Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

Standard

Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines. / Konev, A.S.; Novikov, M.S.; Khlebnikov, A.F.

In: Russian Journal of Organic Chemistry, Vol. 43, No. 2, 02.2007, p. 286-296.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{e8be2ae3262b4e71835858364d36d703,

title = "Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines",

abstract = "N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.",

keywords = "1,3-DIPOLAR CYCLOADDITION, GENERATION, DIFLUOROCARBENE, PYRROLIDINES, DERIVATIVES, OLEFINS, EXAMPLE, ROUTE",

author = "A.S. Konev and M.S. Novikov and A.F. Khlebnikov",

year = "2007",

month = feb,

doi = "10.1134/S1070428007020224",

language = "Английский",

volume = "43",

pages = "286--296",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "2",

}

RIS

TY - JOUR

T1 - Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

AU - Konev, A.S.

AU - Novikov, M.S.

AU - Khlebnikov, A.F.

PY - 2007/2

Y1 - 2007/2

N2 - N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.

AB - N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.

KW - 1,3-DIPOLAR CYCLOADDITION

KW - GENERATION

KW - DIFLUOROCARBENE

KW - PYRROLIDINES

KW - DERIVATIVES

KW - OLEFINS

KW - EXAMPLE

KW - ROUTE

U2 - 10.1134/S1070428007020224

DO - 10.1134/S1070428007020224

M3 - статья

VL - 43

SP - 286

EP - 296

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 2

ER -

ID: 5022843