A Straightforward Synthesis of Oxazino[2,3,4-ij]quinoline Derivatives from 8-Hydroxyquinolines

Abstract

A one-step synthesis of tricyclic dihydrofuro[3,2-f]quinoline or tetracyclic oxazinoquinoline derivatives from hydroxyquinolines and ethyl 2,3-dibromopropanoate is described. 3,4-Dibromobutan-2-one afforded 2-acetylfuro[3,2-h]quinoline derivatives and 2,3-dibromopropanenitrile gave only non-cyclized compounds when reacted with 8-hydroxyquinoline.

Key words

hydroxyquinolines - oxazino[2,3,4-ij]quinolines - ethyl dihydrofuro[3,2-h]quinoline-2-carboxylate - cyclization

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11

Similarly compounds 3a and 4 afforded the analogous Z-cyano derivatives.