New Pathway to the Synthesis of Substituted 4H-3, 1-Benzoxazines

SS Mochalov, RA Gazzaeva, AN Fedotov…

Index: Mochalov; Gazzaeva; Fedotov; Shabarov; Zefirov Chemistry of Heterocyclic Compounds, 2003 , vol. 39, # 6 p. 794 - 801

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Abstract

Abstract The intramolecular rearrangement of N-acyl-2-cyclopropylanilines by the action of protic acids gives substituted 4H-3, 1-benzoxazines. The reaction proceeds in high yield through the formation of benzoxazine precursors, namely, the corresponding 3, 1- benzoxazinium ions, which are stable in acid solution. N-Acylamino-2-alkenylbenzenes, in which the double bond of the alkyl chain is conjugated with the benzene ring, are capable ...