Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles. / Агафонова, Анастасия Викторовна; Павленко, Юлия Игоревна; Сахаров, Павел Алексеевич; Сметанин, Илья Алексеевич; Хлебников, Александр Феодосиевич; Крюкова, Мария Александровна; Новиков, Михаил Сергеевич.
в: Journal of Organic Chemistry, Том 89, № 9, 17.04.2024, стр. 6281–6291.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles
AU - Агафонова, Анастасия Викторовна
AU - Павленко, Юлия Игоревна
AU - Сахаров, Павел Алексеевич
AU - Сметанин, Илья Алексеевич
AU - Хлебников, Александр Феодосиевич
AU - Крюкова, Мария Александровна
AU - Новиков, Михаил Сергеевич
PY - 2024/4/17
Y1 - 2024/4/17
N2 - An efficient protocol for the synthesis of stable 2-azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2-carboxylates with trimethylsilyl cyanide/Bu4NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C-C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2-C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation-cyclization sequence.
AB - An efficient protocol for the synthesis of stable 2-azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2-carboxylates with trimethylsilyl cyanide/Bu4NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C-C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2-C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation-cyclization sequence.
UR - https://www.mendeley.com/catalogue/ee9c3f3f-b597-376d-aa58-e4ff2d1f8d21/
U2 - 10.1021/acs.joc.4c00264
DO - 10.1021/acs.joc.4c00264
M3 - Article
VL - 89
SP - 6281
EP - 6291
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 9
ER -
ID: 119944543