Tetrahedron, volume 66, issue 24, pages 4330-4338
Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides
Rakitin Oleg A
,
Lyssenko Konstantin A.
,
Nelyubina Yulia V.
,
Bolshakov Oleg I
,
Golova Svetlana P
1
,
Bol'shakov Oleg
1
,
Publication type: Journal Article
Publication date: 2010-06-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract The treatment of 5H-1,2,3-dithiazole-5-thiones 1 in chloroform under reflux and 5H-1,2,3-dithiazol-5-ones 2 in THF at room temperature with primary aliphatic amines and benzylamine afforded 1,2,5-thiadiazole-3(2H)-thiones 3 and 1,2,5-thiadiazol-3(2H)-ones 6, respectively. The structure of dithiazolone 3f was confirmed by X-ray diffraction analysis. The reaction of dithiazolone 2e bearing an electron-donating methyl group in the 4-position gave 2-oxoacetamide 7e in high yield. The reaction of thiones 1 with secondary aliphatic amines in DMSO yielded 2-iminothioacetamides 8 in moderate yields together with elemental sulfur. Interestingly, the treatment of dithiazolones 2 with secondary amines under the same conditions afforded 2-oxoacetamides 9—the products of the hydrolysis of corresponding imino derivatives 10, which was isolated as 10b. A general mechanism was proposed for the formation of the products.
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Citations by publishers
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American Chemical Society (ACS)
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3 publications, 30%
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1 publication, 10%
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Wiley
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Wiley
1 publication, 10%
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Thieme
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1 publication, 10%
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1
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Konstantinova L. S. et al. Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides // Tetrahedron. 2010. Vol. 66. No. 24. pp. 4330-4338.
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Konstantinova L. S., Bolshakov O. I., Obruchnikova N. V., Golova S. P., Nelyubina Y. V., Lyssenko K. A., Rakitin O. A., Bol'shakov O., Nelyubina Y. V., Lyssenko K. A., Rakitin O. A. Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides // Tetrahedron. 2010. Vol. 66. No. 24. pp. 4330-4338.
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TY - JOUR
DO - 10.1016/j.tet.2010.04.033
UR - https://doi.org/10.1016%2Fj.tet.2010.04.033
TI - Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides
T2 - Tetrahedron
AU - Konstantinova, Lidia S.
AU - Bolshakov, Oleg I
AU - Obruchnikova, Natalia V.
AU - Golova, Svetlana P
AU - Nelyubina, Yulia V.
AU - Lyssenko, Konstantin A.
AU - Rakitin, Oleg A
AU - Bol'shakov, Oleg
AU - Nelyubina, Yulia V.
AU - Lyssenko, Konstantin A.
AU - Rakitin, Oleg A.
PY - 2010
DA - 2010/06/01 00:00:00
PB - Elsevier
SP - 4330-4338
IS - 24
VL - 66
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2010_Konstantinova,
author = {Lidia S. Konstantinova and Oleg I Bolshakov and Natalia V. Obruchnikova and Svetlana P Golova and Yulia V. Nelyubina and Konstantin A. Lyssenko and Oleg A Rakitin and Oleg Bol'shakov and Yulia V. Nelyubina and Konstantin A. Lyssenko and Oleg A. Rakitin},
title = {Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides},
journal = {Tetrahedron},
year = {2010},
volume = {66},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016%2Fj.tet.2010.04.033},
number = {24},
pages = {4330--4338},
doi = {10.1016/j.tet.2010.04.033}
}
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Konstantinova, Lidia S., et al. “Reactions of 4-substituted 5H-1,2,3-dithiazoles with primary and secondary amines: fast and convenient synthesis of 1,2,5-thiadiazoles, 2-iminothioacetamides and 2-oxoacetamides.” Tetrahedron, vol. 66, no. 24, Jun. 2010, pp. 4330-4338. https://doi.org/10.1016%2Fj.tet.2010.04.033.