4H-3, 1-benzoxazines from benzyl cyclopropanes. First example of acid catalyzed rearrangement in ortho-substituted benzylcyclo-propanes

EV Trofimova, BP Archegov, AN Fedotov…

Index: Trofimova; Archegov; Fedotov; Gazzaeva; Mochalov; Zefirov Chemistry of Heterocyclic Compounds, 2009 , vol. 45, # 9 p. 1095 - 1104

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Citation Number: 2

Abstract

The synthesis of 2-N-acylamino-substituted benzylcyclopropanes has been carried out. It was established that under the action of acids 2-N-acylamino-substituted benzylcyclopropanes are rearranged into the corresponding 4H-3, 1-benzoxazines and not into the expected 3, 1-benzoxazepines. It was shown that a similar type of rearrangement is also characteristic for 2-N-acylamino-substituted allylbenzenes.