The Journal of Organic Chemistry

Displacements at the nitrogen of lithioalkoxylamides by organometallic reagents

P Beak, GW Selling

Index: Beak, Peter; Selling, Gordon W. Journal of Organic Chemistry, 1989 , vol. 54, # 23 p. 5574 - 5580

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Citation Number: 47

Abstract

Cyclizations. This amination strategy can be used to form nitrogen-containing rings. The sequence which begins with the preparation of the appropriate (o-bromo-pheny1) alkanylmethoxylamine by straightforward methodology is illustrated by the synthesis of N- acetylbenzoazetine (l), N-acetyltetrahydroquinoline (2), and N-acetylbenzazapine (3). The key step is double lithiation of the aryl bromide to give an (o-1ithiophenyl) alkyIlithio- ...