Synthesis p. 863 - 867 (1991)
Update date:2022-09-26
Topics:
Katritzky
Hitchings
Zhao
N-Arylmethylene[(benzotriazol-1-yl)arylmethyl]amines 1 are prepared by the reaction of arylaldehydes, benzotriazole, and ammonia in dry ethanol. Deprotonation of these imines with butyllithium yields N-lithiated azomethine ylides 2 which readily undergo 1,3-dipolar cycloaddition with a large range of dipolarophiles. The cyclisations are regiospecific and generally exhibit high stereoselectivity. Benzotriazolate is eliminated during the course of the reaction, and the method thereby provides a route to 2,5-diaryl substituted pyrroles, 3,4-dihydro-2H-pyrroles and c-ring fused 3,4-dihydro-2H-pyrroles.
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Doi:10.1055/s-0037-1611752
(2019)Doi:10.1007/s11164-012-0696-5
(2013)Doi:10.1016/0040-4039(91)80432-6
(1991)Doi:10.1021/acs.joc.8b02919
(2019)Doi:10.1016/j.tetlet.2012.05.141
(2012)Doi:10.1055/s-0031-1290824
(2012)