SYNTHESIS AND REACTIVITY OF A N-ARYL-2-VINYLTETRAHYDRO-4-OXOQUINOLINE

Ethyl ro-1-(3',4',5'-trimethoxyphenyl)-4-oxoquinoline-3- carboxylate 1 was prepared by the reaction of vinylcuprate on ethyl ,5'-trimethoxyp henyl)-4-oxoquinoline-3-carboxylate 9. Different quinolones and a tetr ahydro-4-oxoquinoline have been obtained by oxidation of 1. Depending on the reagent, the initial addition occurs either at only one of the reactive functions, namely the vinyl double bond or the enolate, or at both. New unexpected 1,2-dihydroquinolines were synthesized in attemp ts at protecting the diol obtained by reduction of 1. (C) 1997 Elsevie r Science Ltd. All rights reserved.