Chemical Research in Chinese Universities ›› 1989, Vol. 5 ›› Issue (1): 61-67.

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Syntheses of Benzoxepinoquinolinone and Benzothiepinoquinolinone

Yang Dingqiao, Jiang Guiji, Gao Yongjun   

  1. Department of Chemistry, Yanbian University, Yanji
  • Received:1988-08-05 Online:1989-01-24 Published:2011-09-09

Abstract: l-Benzoxepino(3, 4-b)quinolin-l3(6H)-one and its halogen,alkyl, alkoxy derivatives Va'-d'and 1-benzothiepino(3,4-b}-quinolin- 13 ( 6H)-one Vf, and its alkyl derivatives Vg, weresynthesized through cyclization of 2-(substituted phenoxymethyl)-3-quinolinecarboxylic acids Va-d and 2-[ (un)substituted phen-ylthiomethyll-3-quinolinecarboxylic acids IVf-g in the presence ofpolyphosphoric acid.The acids IV were obtained from the corresponding ethyl-esters @ whcih were prepared through refluxing ethyl 2-bromo-methyl-3-quinolinecarboxylate(1) with substituted phenol or (un)substituted thiophenol in the presence of NaOEt.The compound Vg, was allowed to react with NBS, KaBH4, NH2OH-HCl to give compounds VII, VIII, and IX, respectively.The structures of 24 new compounds have been confirmed by elemental analysis, IR and 1H NMR.

Key words: Ethyl 2-phenylthiomethyl-3-quinolinecarboxylate, 2- phenylthiomethyl-3-quinolinecarboxylic acid, 1-Ben- zoxepino(3, 4-b)quinoline-13(6H)-one, 1-Benzothie- pino(3, Cyclization