Studies on diazepines. XXV. Syntheses of fully unsaturated 1, 4-oxazepines and 1H-1, 4-diazepines using photochemical valence isomerization of tricycloheptene …

J KURITA, K IWATA, T TSUCHIYA

Index: Kurita, Jyoji; Iwata, Kuniyoshi; Tsuchiya, Takashi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 8 p. 3166 - 3174

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Citation Number: 23

Abstract

3-Azatricyclo [4.1. 0.0 2.5] hept-3-ene derivatives prepared from pyridines via five steps were found to be useful synthons for fully unsaturated monocyclic seven-membered heterocyclic rings. Photolysis of the 7-oxa derivatives 15 resulted in valence isomerization with ring opening to give the 1, 4-oxazepines (19), which are the first examples of fully conjugated 1, 4-oxazepines. Similarly, the 7-aza derivatives 16, upon irradiation, afforded the novel 1H- ...