An Efficient Synthesis of 6-Substituted Aminohexahydro-1H-1, 4-diazepines from 2-Substituted Aminopropenals.

H Harada, T Morie, Y Hirokawa, S KATO

Index: Harada, Hiroshi; Morie, Toshiya; Hirokawa, Yoshimi; Kato, Shiro Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 12 p. 2205 - 2212

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Citation Number: 23

Abstract

Swern oxidation of 2-substituted amino-1, 3-propanediols 20a-d, 38, 41, and 42 smoothly proceeded to give the oxidative dehydration products, 2-substituted aminopropenals 17a-d, 43, 45 and 46, respectively. Reaction of the intriguing 2-substituted aminopropenals 17a-d with N-benzyl-N'-methyl-or N, N'-dimethylethylenediamine (12o or 12p) followed by NaBH 4 reduction of the iminium salt intermediates afforded the corresponding 6-substituted ...