Tetrahedron letters

11-(Tetrahydro-3 and 4-pyridinyl) dibenzo [b, e][1, 4] diazepines undergo novel rearrangements on treatment with concentrated HBr

J Cairns, TR Clarkson, JAM Hamersma, DR Rae

Index: Cairns, James; Clarkson, Thomas R.; Hamersma, Johan A.M.; Rae, Duncan R. Tetrahedron Letters, 2002 , vol. 43, # 8 p. 1583 - 1585

Full Text: HTML

Citation Number: 9

Abstract

11-(1, 2, 5, 6-Tetrahydro-1-methyl-3-pyridinyl)-5-methyl-5H-dibenzo [b, e][1, 4] diazepine on heating in conc. HBr afforded trans-5-(2-aminophenyl)-1, 3, 4, 4a, 5, 10a-hexahydro-2- methylbenzo [b][1, 6] naphthyridin-10 (2H)-one in one step. The isomer 11-(1, 2, 5, 6- tetrahydro-1-methyl-4-pyridinyl)-5-methyl-5H-dibenzo [b, e][1, 4] diazepine underwent a novel rearrangement resulting in the pentacycle, 4-amino-5, 13-diaza-13-methyl-bicyclo [ ...