Tetrahedron

The triflic acid-mediated cyclisation of N-benzylcinnamanilides

FD King, S Caddick

Index: King, Frank D.; Caddick, Stephen Tetrahedron, 2013 , vol. 69, # 40 p. 8592 - 8601

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Citation Number: 8

Abstract

Abstract N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2, 4-dihydro- 1H-quinolin-2-ones and 2, 5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho- substituted anilides, N-debenzylation also occurs to give 4-aryl-2, 4-dihydro-1H-quinoline-2- ones.