Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones
Vladimir A. Ogurtsov
1, 2
,
Yury V Karpychev
3, 4
,
Petr V Primakov
5, 6, 7, 8
,
Oleg A. Rakitin
1, 2, 10, 11
3
JSC State Scientific Research Institute “Kristall”; 606007 Dzerzhinsk, Nizhny Novgorod Region Russian Federation
|
4
JSC State Scientific Research Institute “Kristall” 606007 Dzerzhinsk, Nizhny Novgorod Region Russian Federation
|
6
Department of Chemistry; Moscow State; 119899 Moscow Russia
|
8
Department of Chemistry Moscow State 119899 Moscow Russia
|
Publication type: Journal Article
Publication date: 2019-04-05
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of 6,7‐dihydropyrrolo[2,1‐c][1,3]thi‐azino[3,2‐a]pyrazine‐4(11bH)‐(thi)ones from readily available 1,2‐di‐thiolo‐3‐(thi)ones and 3,4‐dihydropyrrolo[1,2‐a]pyrazine is reported. The S2 atom in both monocyclic and fused 1,2‐dithioles is selectively replaced by aminomethylene to afford fused, rigid six‐membered 1,3‐thiazines. The scope of this two‐step one‐pot reaction was investigated: 1,2‐dithiolo‐3‐ones were more reactive than the corresponding 1,2‐dithiole‐3‐thiones. Optimized reaction conditions and a mechanistic rationale for the ring transformation are presented.
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9
Total citations:
9
Citations from 2024:
5
(55.55%)
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Ogurtsov V. A. et al. Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 26. pp. 4149-4158.
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Ogurtsov V. A., Karpychev Y. V., Nelyubina Y. V., Primakov P. V., Koutentis P. A., Rakitin O. A. Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 26. pp. 4149-4158.
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TY - JOUR
DO - 10.1002/ejoc.201900142
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900142
TI - Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones
T2 - European Journal of Organic Chemistry
AU - Ogurtsov, Vladimir A.
AU - Karpychev, Yury V
AU - Nelyubina, Yulia V.
AU - Primakov, Petr V
AU - Koutentis, Panayiotis A.
AU - Rakitin, Oleg A.
PY - 2019
DA - 2019/04/05
PB - Wiley
SP - 4149-4158
IS - 26
VL - 2019
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2019_Ogurtsov,
author = {Vladimir A. Ogurtsov and Yury V Karpychev and Yulia V. Nelyubina and Petr V Primakov and Panayiotis A. Koutentis and Oleg A. Rakitin},
title = {Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones},
journal = {European Journal of Organic Chemistry},
year = {2019},
volume = {2019},
publisher = {Wiley},
month = {apr},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900142},
number = {26},
pages = {4149--4158},
doi = {10.1002/ejoc.201900142}
}
Cite this
MLA
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Ogurtsov, Vladimir A., et al. “Synthesis of 6,7-Dihydropyrrolo[2,1-c][1,3]thiazino[3,2-a]pyrazine-4(11bH)-(thi)ones from 1,2-Dithiolo-3-(thi)ones.” European Journal of Organic Chemistry, vol. 2019, no. 26, Apr. 2019, pp. 4149-4158. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900142.