Synthesis of 1, 3-diazepines and ring contraction to cyanopyrroles

A Reisinger, PV Bernhardt, C Wentrup

Index: Reisinger, Ales; Bernhardt, Paul V.; Wentrup, Curt Organic and Biomolecular Chemistry, 2004 , vol. 2, # 2 p. 246 - 256

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Citation Number: 25

Abstract

Several tetrazolo [1, 5-a] pyridines/2-azidopyridines undergo photochemical nitrogen elimination and ring expansion to 1, 3-diazacyclohepta-1, 2, 4, 6-tetraenes (7, 10, 13, 16, 19, 22) as well as ring cleavage to cyanovinylketenimines (8, 17, 20b) in low temperature Ar matrices. 6, 8-Dichlorotetrazolo [1, 5-a] pyridine/2-azido-3, 5-dichloropridine 6 undergoes ready exchange of the chlorine in position 8 (3) with ROH/RONa. 8-Chloro-6- ...