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The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4 Научная публикация

Журнал Molecules
, E-ISSN: 1420-3049
Вых. Данные Год: 2021, Том: 26, Номер: 19, Номер статьи : 6000, Страниц : DOI: 10.3390/molecules26196000
Ключевые слова Alkylation; Appel reaction; Azepane; Hofmann elimination; Nitroxide
Авторы Khoroshunova Y.V. 1,2 , Morozov D.A. 1 , Taratayko A.I. 1,2 , Dobrynin S.A. 1 , Eltsov I.V. 2 , Rybalova T.V. 1 , Sotnikova Y.S. 1 , Polovyanenko D.N. 1 , Asanbaeva N.B. 1,2 , Kirilyuk I.A. 1
Организации
1 N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, Novosibirsk, 630090, Russian Federation
2 Department of Natural Sciences, Novosibirsk State University, Pirogova Str. 1, Novosibirsk, 630090, Russian Federation

Реферат: Activation of a hydroxyl group towards nucleophilic substitution via reaction with me-thanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes 1a–d (Х = O·; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahy-dro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocy-clopenta[c]azepines (4–6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Библиографическая ссылка: Khoroshunova Y.V. , Morozov D.A. , Taratayko A.I. , Dobrynin S.A. , Eltsov I.V. , Rybalova T.V. , Sotnikova Y.S. , Polovyanenko D.N. , Asanbaeva N.B. , Kirilyuk I.A.
The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4
Molecules. 2021. V.26. N19. 6000 . DOI: 10.3390/molecules26196000 WOS Scopus
Идентификаторы:
Web of science WOS:000707772900001
Scopus 2-s2.0-85116594968
OpenAlex W3202874250
Альметрики: