Kleinpeter, Erich

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orcid::0000-0001-8993-0033
  • Kleinpeter, Erich (11)
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Author's Bibliography

Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond

Rašović, Aleksandar; Blagojević, Vladimir A.; Baranac-Stojanović, Marija; Kleinpeter, Erich; Marković, Rade; Minić, Dragica M.

(Royal Soc Chemistry, Cambridge, 2016)

TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Blagojević, Vladimir A.
AU  - Baranac-Stojanović, Marija
AU  - Kleinpeter, Erich
AU  - Marković, Rade
AU  - Minić, Dragica M.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1934
AB  - Information about the strength of donor-acceptor interactions in push-pull alkenes is valuable, as this so-called "push-pull effect'' influences their chemical reactivity and dynamic behaviour. In this paper, we discuss the applicability of NMR spectral data and barriers to rotation around the CQC double bond to quantify the push-pull effect in biologically important 2-alkylidene-4-oxothiazolidines. While olefinic proton chemical shifts and differences in C-13 NMR chemical shifts of the two carbons constituting the CQC double bond fail to give the correct trend in the electron withdrawing ability of the substituents attached to the exocyclic carbon of the double bond, barriers to rotation prove to be a reliable quantity in providing information about the extent of donor-acceptor interactions in the push-pull systems studied. In particular all relevant kinetic data, that is the Arrhenius parameters ( apparent activation energy Ea and frequency factor A) and activation parameters ( Delta S-double dagger, Delta H-double dagger and Delta G(double dagger)), were determined from the data of the experimentally studied configurational isomerization of ( E)-9a. These results were compared to previously published related data for other two compounds, ( Z)-1b and ( 2E, 5Z)-7, showing that experimentally determined Delta G(double dagger) values are a good indicator of the strength of push-pull character. Theoretical calculations of the rotational barriers of eight selected derivatives excellently correlate with the calculated CQC bond lengths and corroborate the applicability of Delta G(double dagger) for estimation of the strength of the push-pull effect in these and related systems.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond
VL  - 40
IS  - 7
SP  - 6364
EP  - 6373
DO  - 10.1039/c6nj00901h
ER  - 
@article{
author = "Rašović, Aleksandar and Blagojević, Vladimir A. and Baranac-Stojanović, Marija and Kleinpeter, Erich and Marković, Rade and Minić, Dragica M.",
year = "2016",
abstract = "Information about the strength of donor-acceptor interactions in push-pull alkenes is valuable, as this so-called "push-pull effect'' influences their chemical reactivity and dynamic behaviour. In this paper, we discuss the applicability of NMR spectral data and barriers to rotation around the CQC double bond to quantify the push-pull effect in biologically important 2-alkylidene-4-oxothiazolidines. While olefinic proton chemical shifts and differences in C-13 NMR chemical shifts of the two carbons constituting the CQC double bond fail to give the correct trend in the electron withdrawing ability of the substituents attached to the exocyclic carbon of the double bond, barriers to rotation prove to be a reliable quantity in providing information about the extent of donor-acceptor interactions in the push-pull systems studied. In particular all relevant kinetic data, that is the Arrhenius parameters ( apparent activation energy Ea and frequency factor A) and activation parameters ( Delta S-double dagger, Delta H-double dagger and Delta G(double dagger)), were determined from the data of the experimentally studied configurational isomerization of ( E)-9a. These results were compared to previously published related data for other two compounds, ( Z)-1b and ( 2E, 5Z)-7, showing that experimentally determined Delta G(double dagger) values are a good indicator of the strength of push-pull character. Theoretical calculations of the rotational barriers of eight selected derivatives excellently correlate with the calculated CQC bond lengths and corroborate the applicability of Delta G(double dagger) for estimation of the strength of the push-pull effect in these and related systems.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond",
volume = "40",
number = "7",
pages = "6364-6373",
doi = "10.1039/c6nj00901h"
}
Rašović, A., Blagojević, V. A., Baranac-Stojanović, M., Kleinpeter, E., Marković, R.,& Minić, D. M.. (2016). Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 40(7), 6364-6373.
https://doi.org/10.1039/c6nj00901h
Rašović A, Blagojević VA, Baranac-Stojanović M, Kleinpeter E, Marković R, Minić DM. Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond. in New Journal of Chemistry. 2016;40(7):6364-6373.
doi:10.1039/c6nj00901h .
Rašović, Aleksandar, Blagojević, Vladimir A., Baranac-Stojanović, Marija, Kleinpeter, Erich, Marković, Rade, Minić, Dragica M., "Quantification of the push-pull effect in 2-alkylidene-4-oxothiazolidines by using NMR spectral data and barriers to rotation around the C=C bond" in New Journal of Chemistry, 40, no. 7 (2016):6364-6373,
https://doi.org/10.1039/c6nj00901h . .
6
4
8

2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry

Džambaski, Zdravko; Marković, Rade; Kleinpeter, Erich; Baranac-Stojanović, Marija

(Oxford : Pergamon-Elsevier Science Ltd, 2013)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Marković, Rade
AU  - Kleinpeter, Erich
AU  - Baranac-Stojanović, Marija
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1344
AB  - A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry
VL  - 69
IS  - 31
SP  - 6436
EP  - 6447
DO  - 10.1016/j.tet.2013.05.087
ER  - 
@article{
author = "Džambaski, Zdravko and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija",
year = "2013",
abstract = "A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry",
volume = "69",
number = "31",
pages = "6436-6447",
doi = "10.1016/j.tet.2013.05.087"
}
Džambaski, Z., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2013). 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 69(31), 6436-6447.
https://doi.org/10.1016/j.tet.2013.05.087
Džambaski Z, Marković R, Kleinpeter E, Baranac-Stojanović M. 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron. 2013;69(31):6436-6447.
doi:10.1016/j.tet.2013.05.087 .
Džambaski, Zdravko, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry" in Tetrahedron, 69, no. 31 (2013):6436-6447,
https://doi.org/10.1016/j.tet.2013.05.087 . .
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Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives

Rašović, Aleksandar; Koch, Andreas; Kleinpeter, Erich; Marković, Rade

(Oxford : Pergamon-Elsevier Science Ltd, 2013)

TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Koch, Andreas
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1227
AB  - Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives
VL  - 69
IS  - 51
SP  - 10849
EP  - 10857
DO  - 10.1016/j.tet.2013.10.088
ER  - 
@article{
author = "Rašović, Aleksandar and Koch, Andreas and Kleinpeter, Erich and Marković, Rade",
year = "2013",
abstract = "Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives",
volume = "69",
number = "51",
pages = "10849-10857",
doi = "10.1016/j.tet.2013.10.088"
}
Rašović, A., Koch, A., Kleinpeter, E.,& Marković, R.. (2013). Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 69(51), 10849-10857.
https://doi.org/10.1016/j.tet.2013.10.088
Rašović A, Koch A, Kleinpeter E, Marković R. Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives. in Tetrahedron. 2013;69(51):10849-10857.
doi:10.1016/j.tet.2013.10.088 .
Rašović, Aleksandar, Koch, Andreas, Kleinpeter, Erich, Marković, Rade, "Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives" in Tetrahedron, 69, no. 51 (2013):10849-10857,
https://doi.org/10.1016/j.tet.2013.10.088 . .
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Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions

Stojanović, Milovan; Marković, Rade; Kleinpeter, Erich; Baranac-Stojanović, Marija

(Royal Soc Chemistry, Cambridge, 2012)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Marković, Rade
AU  - Kleinpeter, Erich
AU  - Baranac-Stojanović, Marija
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1011
AB  - Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
VL  - 10
IS  - 3
SP  - 575
EP  - 589
DO  - 10.1039/c1ob06451g
ER  - 
@article{
author = "Stojanović, Milovan and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija",
year = "2012",
abstract = "Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions",
volume = "10",
number = "3",
pages = "575-589",
doi = "10.1039/c1ob06451g"
}
Stojanović, M., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2012). Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 10(3), 575-589.
https://doi.org/10.1039/c1ob06451g
Stojanović M, Marković R, Kleinpeter E, Baranac-Stojanović M. Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions. in Organic & Biomolecular Chemistry. 2012;10(3):575-589.
doi:10.1039/c1ob06451g .
Stojanović, Milovan, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions" in Organic & Biomolecular Chemistry, 10, no. 3 (2012):575-589,
https://doi.org/10.1039/c1ob06451g . .
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13

endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines

Stojanović, Milovan; Marković, Rade; Kleinpeter, Erich; Baranac-Stojanović, Marija

(Oxford : Pergamon-Elsevier Science Ltd, 2011)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Marković, Rade
AU  - Kleinpeter, Erich
AU  - Baranac-Stojanović, Marija
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/814
AB  - endo-Mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined as a route to the synthesis of condensed thiazolidines. The scope of these reactions and stereochemical outcome are discussed and explained using quantum chemical calculations.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines
VL  - 67
IS  - 49
SP  - 9541
EP  - 9554
DO  - 10.1016/j.tet.2011.10.011
ER  - 
@article{
author = "Stojanović, Milovan and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija",
year = "2011",
abstract = "endo-Mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined as a route to the synthesis of condensed thiazolidines. The scope of these reactions and stereochemical outcome are discussed and explained using quantum chemical calculations.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines",
volume = "67",
number = "49",
pages = "9541-9554",
doi = "10.1016/j.tet.2011.10.011"
}
Stojanović, M., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2011). endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 67(49), 9541-9554.
https://doi.org/10.1016/j.tet.2011.10.011
Stojanović M, Marković R, Kleinpeter E, Baranac-Stojanović M. endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines. in Tetrahedron. 2011;67(49):9541-9554.
doi:10.1016/j.tet.2011.10.011 .
Stojanović, Milovan, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "endo-Mode cyclizations of vinylogous N-acyliminium ions as a route to the synthesis of condensed thiazolidines" in Tetrahedron, 67, no. 49 (2011):9541-9554,
https://doi.org/10.1016/j.tet.2011.10.011 . .
13
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14

Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives

Baranac-Stojanović, Marija; Klaumuenzer, Ute; Marković, Rade; Kleinpeter, Erich

(Oxford : Pergamon-Elsevier Science Ltd, 2010)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Klaumuenzer, Ute
AU  - Marković, Rade
AU  - Kleinpeter, Erich
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3172
AB  - Structures of a series of push-pull 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives were optimized at the B3LYP/6-31G(d) level of theory in the gas phase and discussed with respect to configurational and conformational stability. Employing the GIAO method, C-13 NMR chemical shifts of the C-2, C-2', C-4 and C-5 atoms were calculated at the same level of theory in the gas phase and with inclusion of solvent, and compared with experimental data. Push-pull effect of all compounds was quantified by means of the quotient pi*/pi, length of the partial double bond, C-13 NMR chemical shift difference (Delta delta(C=C)) and H-1 NMR chemical shifts of olefinic protons. The effect of bromine on donating and accepting ability of other substituents of the push-pull C=C double bond is discussed, too. (C) 2010 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives
VL  - 66
IS  - 46
SP  - 8958
EP  - 8967
DO  - 10.1016/j.tet.2010.09.040
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Klaumuenzer, Ute and Marković, Rade and Kleinpeter, Erich",
year = "2010",
abstract = "Structures of a series of push-pull 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives were optimized at the B3LYP/6-31G(d) level of theory in the gas phase and discussed with respect to configurational and conformational stability. Employing the GIAO method, C-13 NMR chemical shifts of the C-2, C-2', C-4 and C-5 atoms were calculated at the same level of theory in the gas phase and with inclusion of solvent, and compared with experimental data. Push-pull effect of all compounds was quantified by means of the quotient pi*/pi, length of the partial double bond, C-13 NMR chemical shift difference (Delta delta(C=C)) and H-1 NMR chemical shifts of olefinic protons. The effect of bromine on donating and accepting ability of other substituents of the push-pull C=C double bond is discussed, too. (C) 2010 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives",
volume = "66",
number = "46",
pages = "8958-8967",
doi = "10.1016/j.tet.2010.09.040"
}
Baranac-Stojanović, M., Klaumuenzer, U., Marković, R.,& Kleinpeter, E.. (2010). Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 66(46), 8958-8967.
https://doi.org/10.1016/j.tet.2010.09.040
Baranac-Stojanović M, Klaumuenzer U, Marković R, Kleinpeter E. Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives. in Tetrahedron. 2010;66(46):8958-8967.
doi:10.1016/j.tet.2010.09.040 .
Baranac-Stojanović, Marija, Klaumuenzer, Ute, Marković, Rade, Kleinpeter, Erich, "Structure, configuration, conformation and quantification of the push pull-effect of 2-alkylidene-4-thiazolidinones and 2-alkylidene-4,5-fused bicyclic thiazolidine derivatives" in Tetrahedron, 66, no. 46 (2010):8958-8967,
https://doi.org/10.1016/j.tet.2010.09.040 . .
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High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety

Baranac-Stojanović, Marija; Tatar, Jovana; Kleinpeter, Erich; Marković, Rade

(Georg Thieme Verlag Kg, Stuttgart, 2008)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Tatar, Jovana
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/457
AB  - A new series of unsubstituted and substituted pyridinium salts bearing a 4-oxothiazolidinyl moiety has been prepared by an efficient rearrangement of 2-(l-bromoalkylidene)thiazolidin-4-ones. The process is based on three steps, namely carbon - bromine cleavage, bromine transfer, and substitution, each induced by pyridine or its derivatives, acting as base and reactant.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety
IS  - 13
SP  - 2117
EP  - 2121
DO  - 10.1055/s-2008-1067113
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Tatar, Jovana and Kleinpeter, Erich and Marković, Rade",
year = "2008",
abstract = "A new series of unsubstituted and substituted pyridinium salts bearing a 4-oxothiazolidinyl moiety has been prepared by an efficient rearrangement of 2-(l-bromoalkylidene)thiazolidin-4-ones. The process is based on three steps, namely carbon - bromine cleavage, bromine transfer, and substitution, each induced by pyridine or its derivatives, acting as base and reactant.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety",
number = "13",
pages = "2117-2121",
doi = "10.1055/s-2008-1067113"
}
Baranac-Stojanović, M., Tatar, J., Kleinpeter, E.,& Marković, R.. (2008). High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety. in Synthesis
Georg Thieme Verlag Kg, Stuttgart.(13), 2117-2121.
https://doi.org/10.1055/s-2008-1067113
Baranac-Stojanović M, Tatar J, Kleinpeter E, Marković R. High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety. in Synthesis. 2008;(13):2117-2121.
doi:10.1055/s-2008-1067113 .
Baranac-Stojanović, Marija, Tatar, Jovana, Kleinpeter, Erich, Marković, Rade, "High-yield synthesis of substituted and unsubstituted pyridinium salts containing a 4-oxothiazolidine moiety" in Synthesis, no. 13 (2008):2117-2121,
https://doi.org/10.1055/s-2008-1067113 . .
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13

CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"

Rašović, Aleksandar; Steel, Peter J.; Kleinpeter, Erich; Marković, Rade

(The Cambridge Crystallographic Data Centre (CCDC), 2007)

TY  - DATA
AU  - Rašović, Aleksandar
AU  - Steel, Peter J.
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4589
AB  - JEYHUR : 2-ethyl-6-phenyl-2,3-dihydro-4H-1,3-thiazine-4-thione Space Group: P 1 (2), Cell: a 5.6687(8)Å b 11.0149(15)Å c 11.056(2)Å, α 116.540(9)° β 94.285(10)° γ 102.679(7)°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"
DO  - 10.5517/ccndh7r
ER  - 
@misc{
author = "Rašović, Aleksandar and Steel, Peter J. and Kleinpeter, Erich and Marković, Rade",
year = "2007",
abstract = "JEYHUR : 2-ethyl-6-phenyl-2,3-dihydro-4H-1,3-thiazine-4-thione Space Group: P 1 (2), Cell: a 5.6687(8)Å b 11.0149(15)Å c 11.056(2)Å, α 116.540(9)° β 94.285(10)° γ 102.679(7)°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"",
doi = "10.5517/ccndh7r"
}
Rašović, A., Steel, P. J., Kleinpeter, E.,& Marković, R.. (2007). CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccndh7r
Rašović A, Steel PJ, Kleinpeter E, Marković R. CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions". 2007;.
doi:10.5517/ccndh7r .
Rašović, Aleksandar, Steel, Peter J., Kleinpeter, Erich, Marković, Rade, "CCDC 607824: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"" (2007),
https://doi.org/10.5517/ccndh7r . .

CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"

Rašović, Aleksandar; Steel, Peter J.; Kleinpeter, Erich; Marković, Rade

(The Cambridge Crystallographic Data Centre (CCDC), 2007)

TY  - DATA
AU  - Rašović, Aleksandar
AU  - Steel, Peter J.
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4588
AB  - JEYHOL : 2-methyl-6-phenyl-4λ4-[1,2]dithiolo[1,5-b][1,2,4]dithiazole Space Group: P 21/c (14), Cell: a 13.4197(7)Å b 7.2797(4)Å c 11.8980(6)Å, α 90° β 108.161(2)° γ 90°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"
DO  - 10.5517/ccndh6q
ER  - 
@misc{
author = "Rašović, Aleksandar and Steel, Peter J. and Kleinpeter, Erich and Marković, Rade",
year = "2007",
abstract = "JEYHOL : 2-methyl-6-phenyl-4λ4-[1,2]dithiolo[1,5-b][1,2,4]dithiazole Space Group: P 21/c (14), Cell: a 13.4197(7)Å b 7.2797(4)Å c 11.8980(6)Å, α 90° β 108.161(2)° γ 90°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"",
doi = "10.5517/ccndh6q"
}
Rašović, A., Steel, P. J., Kleinpeter, E.,& Marković, R.. (2007). CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccndh6q
Rašović A, Steel PJ, Kleinpeter E, Marković R. CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions". 2007;.
doi:10.5517/ccndh6q .
Rašović, Aleksandar, Steel, Peter J., Kleinpeter, Erich, Marković, Rade, "CCDC 607823: Experimental Crystal Structure Determination. Crystallographic data for "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions"" (2007),
https://doi.org/10.5517/ccndh6q . .

Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions

Rašović, Aleksandar; Steel, Peter J.; Kleinpeter, Erich; Marković, Rade

(Elsevier, 2007)

TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Steel, Peter J.
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4587
AB  - A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.
PB  - Elsevier
T2  - Tetrahedron
T1  - Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions
VL  - 63
IS  - 9
SP  - 1937
EP  - 1945
DO  - 10.1016/j.tet.2006.12.075
ER  - 
@article{
author = "Rašović, Aleksandar and Steel, Peter J. and Kleinpeter, Erich and Marković, Rade",
year = "2007",
abstract = "A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions",
volume = "63",
number = "9",
pages = "1937-1945",
doi = "10.1016/j.tet.2006.12.075"
}
Rašović, A., Steel, P. J., Kleinpeter, E.,& Marković, R.. (2007). Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron
Elsevier., 63(9), 1937-1945.
https://doi.org/10.1016/j.tet.2006.12.075
Rašović A, Steel PJ, Kleinpeter E, Marković R. Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron. 2007;63(9):1937-1945.
doi:10.1016/j.tet.2006.12.075 .
Rašović, Aleksandar, Steel, Peter J., Kleinpeter, Erich, Marković, Rade, "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions" in Tetrahedron, 63, no. 9 (2007):1937-1945,
https://doi.org/10.1016/j.tet.2006.12.075 . .
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Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions

Rašović, Aleksandar; Steel, Peter J.; Kleinpeter, Erich; Marković, Rade

(Elsevier, 2007)

TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Steel, Peter J.
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4255
AB  - A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.
PB  - Elsevier
T2  - Tetrahedron
T1  - Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions
VL  - 63
IS  - 9
SP  - 1937
EP  - 1945
DO  - 10.1016/j.tet.2006.12.075
ER  - 
@article{
author = "Rašović, Aleksandar and Steel, Peter J. and Kleinpeter, Erich and Marković, Rade",
year = "2007",
abstract = "A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions",
volume = "63",
number = "9",
pages = "1937-1945",
doi = "10.1016/j.tet.2006.12.075"
}
Rašović, A., Steel, P. J., Kleinpeter, E.,& Marković, R.. (2007). Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron
Elsevier., 63(9), 1937-1945.
https://doi.org/10.1016/j.tet.2006.12.075
Rašović A, Steel PJ, Kleinpeter E, Marković R. Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron. 2007;63(9):1937-1945.
doi:10.1016/j.tet.2006.12.075 .
Rašović, Aleksandar, Steel, Peter J., Kleinpeter, Erich, Marković, Rade, "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions" in Tetrahedron, 63, no. 9 (2007):1937-1945,
https://doi.org/10.1016/j.tet.2006.12.075 . .
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