European Journal of Organic Chemistry

, том 2019 , издание 26 , страницы 4149-4158

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

Тип публикации: Journal Article

Дата публикации: 2019-04-05

Wiley

European Journal of Organic Chemistry

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SJR: 0.558

CiteScore: 4.3

Impact factor: 2.7

ISSN: 1434193X, 10990690

DOI: 10.1002/ejoc.201900142

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Organic Chemistry

Physical and Theoretical Chemistry

Краткое описание

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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Доценко Виктор

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Северо-Кавказский федеральный университет

Кубанский государственный университет

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Active methylene compounds

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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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@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}

}

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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.