HOFMANN ELIMINATION OF HETEROCYCLES CONTAINING BRIDGEHEAD HYDRAZINES .I. 2,6-BENZODIAZONINE AND DIBENZO[C,H][1,6]DIAZECINE DERIVATIVES

Treatment of the methyl halide salts of the bridgehead hydrazines, 5-(p-chlorophenyl)-2,3,5,10-tetrahydro-1H-pyrazolo[ 1,2-6]phthalazine (9) and 5,7,12,14-tetrahydrophthalazino[2,3-b]phthalazine(19), with sodium methoxide-methanol gave the medium-sized heterocycles 1-(p-chlorophenyl)-6-methyl-4,5,6,7-tetrahydro-3H-2,6-benzodiazonine (10) and 6-methyl-5,6,7,14-tetrahydrodibenzo[c,h] [1,6]diazecine (22). The lithium aluminum hydride reduction of 2-(4-chlorobutyl)-4-p-chlorophenylphthalazin-1(2H)-one (5e) resulted in an unusual N-N cleavage and ring formation to give 2-pyrrolidinomethylbenzhydrylamine (16). © 1969, American Chemical Society. All rights reserved.