Synthesis and Halogenocyclization of 2-Allyloxyquinoline Derivatives

Abstract

Alkylation of 4,8-dimethyl- and 4,6,8-trimethylquinolin-2(1H)-one with allyl bromide in the presence of a base proceeds at the oxygen and nitrogen atoms with the predominant formation of the O-isomer. The reaction of 2-allyloxyquinolines with halogens leads to the formation of oxazolo[3,2-a]quinolinium salts. Structure of 1-bromomethyl-5,7,9-trimethyl-1,2-dihydro[1,3]oxazolo[3,2-a]quinolinium iododibromide was established by single crystal X-ray diffraction method.