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Synthesis 1991; 1991(10): 863-867
DOI: 10.1055/s-1991-26595
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The Synthesis of Pyrroles and Dihydropyrroles by 1,3-Dipolar Cyclisations of N-Arylmethylene[(benzotriazol-1-yl)arylmethyl]amines

Alan R. Katritzky* , Gregory J. Hitchings, Xiaohong Zhao
  • *Department of Chemistry, University of Florida, Gainesville, FL 32611-2046, USA
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Publication Date:
29 April 2002 (online)

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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.