Synthesis and reactivity of a N-aryl-2-vinyltetrahydro-4-oxoquinoline

Add time:07/21/2019    Source:sciencedirect.com

Ethyl 2-ethenyl-6,7-methylenedioxy-1,2,3,4,-tetrahydro-1-(3′,4′,5′-trimethoxyphenyl)-4-oxoquinoline-3-carboxylate 1 was prepared by the reaction of vinylcuprate on ethyl 1,4-dihydro-6,7-methylenedioxy-1-(3′,4′,5′-trimethoxyphenyl)-4-oxoquinoline-3-carboxylate 9. Different quinolones and a tetrahydro-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 attempts at protecting the diol obtained by reduction of 1.

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