Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost

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Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (en)
Тиазолидни и синтетички аналози: реактивност, примена и биолошка активност (sr)
Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (sr_RS)
Authors

Publications

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

Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions

Džambaski, Zdravko; Stojanović, Milovan; Baranac-Stojanović, Marija; Minić, Dragica M.; Marković, Rade

(Serbian Chemical Soc, Belgrade, 2011)

TY  - JOUR
AU  - Džambaski, Zdravko
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
AU  - Minić, Dragica M.
AU  - Marković, Rade
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/910
AB  - Configurational isomerization of stereo-defined 5-substituted and unsubstituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by 1H-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolecular hydrogen bonding and directional non-bonded 1,5-type S∙∙∙O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z→E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established.
AB  - Konfiguraciona izomerizacija stereodefinisanih 5-supstituisanih i nesupstituisanih 2-alkiliden-4-oksotiazolidina 1 u čvrstom stanju, pri čemu se stvara Z/E smesa u različitim odnosima, proučavana je pomoću 1H-NMR spektroskopije, rendgenske kristalografije praha i diferencijalne skenirajuće kalorimetrije (DSK). Odnos Z/E izomera može se objasniti u kontekstu nekovalentnih interakcija, koje obuhvataju intermolekulsko i intramolekulsko vodonično vezivanje i usmerene nevezivne S∙∙∙O interakcije 1,5-tipa. Rendgenska kristalografija praha odabranog kristalnog (Z)-4-oksotiazolidinskog supstrata, potvrdila je transformaciju u amorfno stanje u toku ireverzibilnog Z→E procesa. Postavljena je korelacija između prethodnih rezultata koji se odnose na Z/E izomerizaciju u rastvoru, i sada, u čvrstom stanju.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions
T1  - Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija
VL  - 76
IS  - 3
SP  - 317
EP  - 328
DO  - 10.2298/JSC100607038D
ER  - 
@article{
author = "Džambaski, Zdravko and Stojanović, Milovan and Baranac-Stojanović, Marija and Minić, Dragica M. and Marković, Rade",
year = "2011",
abstract = "Configurational isomerization of stereo-defined 5-substituted and unsubstituted 2-alkylidene-4-oxothiazolidines (1) in the solid state, giving the Z/E mixtures in various ratios, was investigated by 1H-NMR spectroscopy, X-ray powder crystallography and differential scanning calorimetry (DSC). The Z/E composition can be rationalized in terms of non-covalent interactions, involving intermolecular and intramolecular hydrogen bonding and directional non-bonded 1,5-type S∙∙∙O interactions. X-Ray powder crystallography, using selected crystalline (Z)-4-oxothiazolidine substrate, revealed transformation to the amorphous state during the irreversible Z→E process. A correlation between previous results on the Z/E isomerization in solution and now in the solid state was established., Konfiguraciona izomerizacija stereodefinisanih 5-supstituisanih i nesupstituisanih 2-alkiliden-4-oksotiazolidina 1 u čvrstom stanju, pri čemu se stvara Z/E smesa u različitim odnosima, proučavana je pomoću 1H-NMR spektroskopije, rendgenske kristalografije praha i diferencijalne skenirajuće kalorimetrije (DSK). Odnos Z/E izomera može se objasniti u kontekstu nekovalentnih interakcija, koje obuhvataju intermolekulsko i intramolekulsko vodonično vezivanje i usmerene nevezivne S∙∙∙O interakcije 1,5-tipa. Rendgenska kristalografija praha odabranog kristalnog (Z)-4-oksotiazolidinskog supstrata, potvrdila je transformaciju u amorfno stanje u toku ireverzibilnog Z→E procesa. Postavljena je korelacija između prethodnih rezultata koji se odnose na Z/E izomerizaciju u rastvoru, i sada, u čvrstom stanju.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions, Termalna Z/E izomerizacija 2-alkiliden-4-oksotiazolidina u čvrstom stanju - uticaj nekovalentnih interakcija",
volume = "76",
number = "3",
pages = "317-328",
doi = "10.2298/JSC100607038D"
}
Džambaski, Z., Stojanović, M., Baranac-Stojanović, M., Minić, D. M.,& Marković, R.. (2011). Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 76(3), 317-328.
https://doi.org/10.2298/JSC100607038D
Džambaski Z, Stojanović M, Baranac-Stojanović M, Minić DM, Marković R. Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions. in Journal of the Serbian Chemical Society. 2011;76(3):317-328.
doi:10.2298/JSC100607038D .
Džambaski, Zdravko, Stojanović, Milovan, Baranac-Stojanović, Marija, Minić, Dragica M., Marković, Rade, "Thermal solid-state Z/E isomerization of 2-alkylidene-4-oxothiazolidines: Effects of non-covalent interactions" in Journal of the Serbian Chemical Society, 76, no. 3 (2011):317-328,
https://doi.org/10.2298/JSC100607038D . .
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7

Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide

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

(Oxford : Pergamon-Elsevier Science Ltd, 2011)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Marković, Rade
AU  - Stojanović, Milovan
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/936
AB  - Direct oxidation of enolizable ketones to α-hydroxy derivatives, vicinal dicarbonyls or tricarbonyl compounds has been achieved by a catalytic amount of 2-alkylidene-4-oxothiazolidine vinyl bromide in DMSO as a solvent. The yields range from moderate to good.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide
VL  - 67
IS  - 41
SP  - 8000
EP  - 8008
DO  - 10.1016/j.tet.2011.08.022
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Marković, Rade and Stojanović, Milovan",
year = "2011",
abstract = "Direct oxidation of enolizable ketones to α-hydroxy derivatives, vicinal dicarbonyls or tricarbonyl compounds has been achieved by a catalytic amount of 2-alkylidene-4-oxothiazolidine vinyl bromide in DMSO as a solvent. The yields range from moderate to good.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide",
volume = "67",
number = "41",
pages = "8000-8008",
doi = "10.1016/j.tet.2011.08.022"
}
Baranac-Stojanović, M., Marković, R.,& Stojanović, M.. (2011). Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 67(41), 8000-8008.
https://doi.org/10.1016/j.tet.2011.08.022
Baranac-Stojanović M, Marković R, Stojanović M. Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide. in Tetrahedron. 2011;67(41):8000-8008.
doi:10.1016/j.tet.2011.08.022 .
Baranac-Stojanović, Marija, Marković, Rade, Stojanović, Milovan, "Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide" in Tetrahedron, 67, no. 41 (2011):8000-8008,
https://doi.org/10.1016/j.tet.2011.08.022 . .
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17
18

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 . .
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13

Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation

Sazonov, P. K.; Džambaski, Zdravko; Shtern, M. M.; Marković, Rade; Beletskaya, I. P.

(Oxford : Pergamon-Elsevier Science Ltd, 2011)

TY  - JOUR
AU  - Sazonov, P. K.
AU  - Džambaski, Zdravko
AU  - Shtern, M. M.
AU  - Marković, Rade
AU  - Beletskaya, I. P.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/927
AB  - Bromophilic attack by the transition metal carbonyl anion, [Re(CO)(5)]Na (pK(a) = 21.1), on 2-(1-bromoalkylidene)thiazolidin-4-ones is significantly faster than abstraction of an acidic lactam hydrogen (pK(a) similar to 17-18), when the generated carbanion is stabilized by an alpha-CN or alpha-PhCO group. The bromophilic reaction of 2-(1-bromoalkylidene)thiazolidin-4-one, having an alpha-CN electron-withdrawing group, resulted in formation of a new metallacyclic anionic complex. With less reactive vinyl bromides, containing an alpha-CONHPh or alpha-CO(2)Et group, only deprotonation is observed. The role of the metal carbonyl anion is highlighted by a comparison with the 9-methylfluorenide carbanion (pK(a) of 9-methylfluorene is 22.3), which reacts exclusively via a deprotonation pathway.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation
VL  - 52
IS  - 1
SP  - 29
EP  - 33
DO  - 10.1016/j.tetlet.2010.10.112
ER  - 
@article{
author = "Sazonov, P. K. and Džambaski, Zdravko and Shtern, M. M. and Marković, Rade and Beletskaya, I. P.",
year = "2011",
abstract = "Bromophilic attack by the transition metal carbonyl anion, [Re(CO)(5)]Na (pK(a) = 21.1), on 2-(1-bromoalkylidene)thiazolidin-4-ones is significantly faster than abstraction of an acidic lactam hydrogen (pK(a) similar to 17-18), when the generated carbanion is stabilized by an alpha-CN or alpha-PhCO group. The bromophilic reaction of 2-(1-bromoalkylidene)thiazolidin-4-one, having an alpha-CN electron-withdrawing group, resulted in formation of a new metallacyclic anionic complex. With less reactive vinyl bromides, containing an alpha-CONHPh or alpha-CO(2)Et group, only deprotonation is observed. The role of the metal carbonyl anion is highlighted by a comparison with the 9-methylfluorenide carbanion (pK(a) of 9-methylfluorene is 22.3), which reacts exclusively via a deprotonation pathway.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation",
volume = "52",
number = "1",
pages = "29-33",
doi = "10.1016/j.tetlet.2010.10.112"
}
Sazonov, P. K., Džambaski, Z., Shtern, M. M., Marković, R.,& Beletskaya, I. P.. (2011). Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 52(1), 29-33.
https://doi.org/10.1016/j.tetlet.2010.10.112
Sazonov PK, Džambaski Z, Shtern MM, Marković R, Beletskaya IP. Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation. in Tetrahedron Letters. 2011;52(1):29-33.
doi:10.1016/j.tetlet.2010.10.112 .
Sazonov, P. K., Džambaski, Zdravko, Shtern, M. M., Marković, Rade, Beletskaya, I. P., "Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation" in Tetrahedron Letters, 52, no. 1 (2011):29-33,
https://doi.org/10.1016/j.tetlet.2010.10.112 . .
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4
8

Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles

Baranac-Stojanović, Marija; Tatar, Jovana; Stojanović, Milovan; Marković, Rade

(Oxford : Pergamon-Elsevier Science Ltd, 2010)

TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Tatar, Jovana
AU  - Stojanović, Milovan
AU  - Marković, Rade
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/700
AB  - Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph(3)P, AcS(-), CN(-), I(-), F(-), Ac(2)CH(-) and N(3)(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et(3)N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles
VL  - 66
IS  - 34
SP  - 6873
EP  - 6884
DO  - 10.1016/j.tet.2010.06.057
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Tatar, Jovana and Stojanović, Milovan and Marković, Rade",
year = "2010",
abstract = "Vinyl bromides derived from 2-alkylidene-4-oxothiazolidines represent a class of vinyl halides, which readily undergo a bromophilic attack by a range of nucleophiles. With Ph(3)P, AcS(-), CN(-), I(-), F(-), Ac(2)CH(-) and N(3)(-) the attack ends up with reductive debromination, whereas the bromine substitution takes place with KSCN. When acetate anion and organic bases, such as pyridine, Et(3)N or morpholine, are employed as nucleophiles the initial bromophilic attack is followed by bromine migration to the C(5) position of the ring, allowing the C(5) functionalization of this heterocyclic system.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles",
volume = "66",
number = "34",
pages = "6873-6884",
doi = "10.1016/j.tet.2010.06.057"
}
Baranac-Stojanović, M., Tatar, J., Stojanović, M.,& Marković, R.. (2010). Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 66(34), 6873-6884.
https://doi.org/10.1016/j.tet.2010.06.057
Baranac-Stojanović M, Tatar J, Stojanović M, Marković R. Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles. in Tetrahedron. 2010;66(34):6873-6884.
doi:10.1016/j.tet.2010.06.057 .
Baranac-Stojanović, Marija, Tatar, Jovana, Stojanović, Milovan, Marković, Rade, "Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles" in Tetrahedron, 66, no. 34 (2010):6873-6884,
https://doi.org/10.1016/j.tet.2010.06.057 . .
11
11
11

Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles

Tatar, Jovana; Marković, Rade; Stojanović, Milovan; Baranac-Stojanović, Marija

(Oxford : Pergamon-Elsevier Science Ltd, 2010)

TY  - JOUR
AU  - Tatar, Jovana
AU  - Marković, Rade
AU  - Stojanović, Milovan
AU  - Baranac-Stojanović, Marija
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/703
AB  - alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles
VL  - 51
IS  - 37
SP  - 4851
EP  - 4855
DO  - 10.1016/j.tetlet.2010.07.057
ER  - 
@article{
author = "Tatar, Jovana and Marković, Rade and Stojanović, Milovan and Baranac-Stojanović, Marija",
year = "2010",
abstract = "alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles",
volume = "51",
number = "37",
pages = "4851-4855",
doi = "10.1016/j.tetlet.2010.07.057"
}
Tatar, J., Marković, R., Stojanović, M.,& Baranac-Stojanović, M.. (2010). Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 51(37), 4851-4855.
https://doi.org/10.1016/j.tetlet.2010.07.057
Tatar J, Marković R, Stojanović M, Baranac-Stojanović M. Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles. in Tetrahedron Letters. 2010;51(37):4851-4855.
doi:10.1016/j.tetlet.2010.07.057 .
Tatar, Jovana, Marković, Rade, Stojanović, Milovan, Baranac-Stojanović, Marija, "Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles" in Tetrahedron Letters, 51, no. 37 (2010):4851-4855,
https://doi.org/10.1016/j.tetlet.2010.07.057 . .
10
8
8

Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds

Tatar, Jovana; Baranac-Stojanović, Marija; Stojanović, Milovan; Marković, Rade

(Oxford : Pergamon-Elsevier Science Ltd, 2009)

TY  - JOUR
AU  - Tatar, Jovana
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Marković, Rade
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/595
AB  - An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds
VL  - 50
IS  - 6
SP  - 700
EP  - 703
DO  - 10.1016/j.tetlet.2008.11.104
ER  - 
@article{
author = "Tatar, Jovana and Baranac-Stojanović, Marija and Stojanović, Milovan and Marković, Rade",
year = "2009",
abstract = "An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds",
volume = "50",
number = "6",
pages = "700-703",
doi = "10.1016/j.tetlet.2008.11.104"
}
Tatar, J., Baranac-Stojanović, M., Stojanović, M.,& Marković, R.. (2009). Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 50(6), 700-703.
https://doi.org/10.1016/j.tetlet.2008.11.104
Tatar J, Baranac-Stojanović M, Stojanović M, Marković R. Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds. in Tetrahedron Letters. 2009;50(6):700-703.
doi:10.1016/j.tetlet.2008.11.104 .
Tatar, Jovana, Baranac-Stojanović, Marija, Stojanović, Milovan, Marković, Rade, "Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds" in Tetrahedron Letters, 50, no. 6 (2009):700-703,
https://doi.org/10.1016/j.tetlet.2008.11.104 . .
16
17
19

Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions

Stojanović, Milovan; Marković, Rade

(2009)

TY  - JOUR
AU  - Stojanović, Milovan
AU  - Marković, Rade
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/580
AB  - Synthesis of new thiazolidine-fused five-, six-, and seven-membered heterocycles through vinylogous N-acyliminium ion-cyclization sequence, involving positions 3 and 4 of the thiazolidine ring, is described. The formation of bicyclic products, arising by generally disfavored 5-endo-trig cyclization initiated by sulfur atom acting as a nucleophile, indicates the preparative value of this method.
T2  - Synlett
T1  - Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions
IS  - 12
SP  - 1997
EP  - 2001
DO  - 10.1055/s-0029-1217532
ER  - 
@article{
author = "Stojanović, Milovan and Marković, Rade",
year = "2009",
abstract = "Synthesis of new thiazolidine-fused five-, six-, and seven-membered heterocycles through vinylogous N-acyliminium ion-cyclization sequence, involving positions 3 and 4 of the thiazolidine ring, is described. The formation of bicyclic products, arising by generally disfavored 5-endo-trig cyclization initiated by sulfur atom acting as a nucleophile, indicates the preparative value of this method.",
journal = "Synlett",
title = "Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions",
number = "12",
pages = "1997-2001",
doi = "10.1055/s-0029-1217532"
}
Stojanović, M.,& Marković, R.. (2009). Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions. in Synlett(12), 1997-2001.
https://doi.org/10.1055/s-0029-1217532
Stojanović M, Marković R. Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions. in Synlett. 2009;(12):1997-2001.
doi:10.1055/s-0029-1217532 .
Stojanović, Milovan, Marković, Rade, "Synthesis of the first thiazolidine-condensed five-, six-, and seven-membered heterocycles via cyclization of vinylogous N-acyliminium ions" in Synlett, no. 12 (2009):1997-2001,
https://doi.org/10.1055/s-0029-1217532 . .
10
14
17

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 . .
5
9
13

Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry

Minić, Dragica M.; Cekić, I.; Pastor, Ferenc T.; Jovanović, Vladislava M.; Marković, Rade

(Maik Nauka/Interperiodica/Springer, New York, 2007)

TY  - CONF
AU  - Minić, Dragica M.
AU  - Cekić, I.
AU  - Pastor, Ferenc T.
AU  - Jovanović, Vladislava M.
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/352
AB  - This study demonstrates the electrochemical activity of selected 2-alkylidene-4-oxothiazolidine compounds containing different substituents at the C5-position on the Pt-electrode in 0.1 M TBAHFP + MeCN in the potential range from -2 V to 2 V. The mechanism of electrode processes is discussed. It is shown that a chemical step is involved in irreversible electrochemical processes. The effect of the substituent at the C5-position on reduction and oxidation potentials is also noted. The regions of a linear dependence of the current peak on the concentration of the compounds examined are determined.
PB  - Maik Nauka/Interperiodica/Springer, New York
C3  - Russian Journal of Physical Chemistry A
T1  - Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry
VL  - 81
IS  - 9
SP  - 1458
EP  - 1462
DO  - 10.1134/S003602440709021X
ER  - 
@conference{
author = "Minić, Dragica M. and Cekić, I. and Pastor, Ferenc T. and Jovanović, Vladislava M. and Marković, Rade",
year = "2007",
abstract = "This study demonstrates the electrochemical activity of selected 2-alkylidene-4-oxothiazolidine compounds containing different substituents at the C5-position on the Pt-electrode in 0.1 M TBAHFP + MeCN in the potential range from -2 V to 2 V. The mechanism of electrode processes is discussed. It is shown that a chemical step is involved in irreversible electrochemical processes. The effect of the substituent at the C5-position on reduction and oxidation potentials is also noted. The regions of a linear dependence of the current peak on the concentration of the compounds examined are determined.",
publisher = "Maik Nauka/Interperiodica/Springer, New York",
journal = "Russian Journal of Physical Chemistry A",
title = "Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry",
volume = "81",
number = "9",
pages = "1458-1462",
doi = "10.1134/S003602440709021X"
}
Minić, D. M., Cekić, I., Pastor, F. T., Jovanović, V. M.,& Marković, R.. (2007). Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry. in Russian Journal of Physical Chemistry A
Maik Nauka/Interperiodica/Springer, New York., 81(9), 1458-1462.
https://doi.org/10.1134/S003602440709021X
Minić DM, Cekić I, Pastor FT, Jovanović VM, Marković R. Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry. in Russian Journal of Physical Chemistry A. 2007;81(9):1458-1462.
doi:10.1134/S003602440709021X .
Minić, Dragica M., Cekić, I., Pastor, Ferenc T., Jovanović, Vladislava M., Marković, Rade, "Electrochemical behavior of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives studied by cyclic voltammetry" in Russian Journal of Physical Chemistry A, 81, no. 9 (2007):1458-1462,
https://doi.org/10.1134/S003602440709021X . .
2
2
2