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Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones

Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona

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2004
137.pdf (152.0Kb)
Authors
Marković, Rade
Rašović, Aleksandar
Baranac, Marija M.
Stojanović, Milovan
Steel, Peter
Jovetić, Stanka L.
Article (Published version)
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Abstract
The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.
Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije.
Keywords:
thiazolidine / enaminone / Lawesson’s reagent / 1,2-dithiole / 3 / 3aλ4,4-trithia
Source:
Journal of the Serbian Chemical Society, 2004, 69, 11, 909-918
Publisher:
  • Serbian Chemical Society
Funding / projects:
  • Project MESTD, br. 1709

DOI: 10.2298/JSC0411909M

ISSN: 0352-5139

WoS: 000226120300010

Scopus: 2-s2.0-31544465959
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/139
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Marković, Rade
AU  - Rašović, Aleksandar
AU  - Baranac, Marija M.
AU  - Stojanović, Milovan
AU  - Steel, Peter
AU  - Jovetić, Stanka L.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/139
AB  - The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.
AB  - Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones
T1  - Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona
VL  - 69
IS  - 11
SP  - 909
EP  - 918
DO  - 10.2298/JSC0411909M
ER  - 
@article{
author = "Marković, Rade and Rašović, Aleksandar and Baranac, Marija M. and Stojanović, Milovan and Steel, Peter and Jovetić, Stanka L.",
year = "2004",
abstract = "The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step., Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones, Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona",
volume = "69",
number = "11",
pages = "909-918",
doi = "10.2298/JSC0411909M"
}
Marković, R., Rašović, A., Baranac, M. M., Stojanović, M., Steel, P.,& Jovetić, S. L.. (2004). Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(11), 909-918.
https://doi.org/10.2298/JSC0411909M
Marković R, Rašović A, Baranac MM, Stojanović M, Steel P, Jovetić SL. Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. in Journal of the Serbian Chemical Society. 2004;69(11):909-918.
doi:10.2298/JSC0411909M .
Marković, Rade, Rašović, Aleksandar, Baranac, Marija M., Stojanović, Milovan, Steel, Peter, Jovetić, Stanka L., "Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):909-918,
https://doi.org/10.2298/JSC0411909M . .

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