Molecular diversity of cycloaddition reactions of the functionalized pyridinium salts with 3-phenacylideneoxindoles

Abstract

The cycloaddition reactions of a series of functionalized pyridinium salts, which were generated from reaction of pyridine with active alkyl halides such as p-nitrobenzyl bromide, N,N-diethyl chloroacetamide and phenacyl bromides with 3-phenacylideneoxindoles in the presence of triethylamine showed very interesting molecular diversities. A series of the functionalized spiro[cyclopropane-1,3′-indolines], and 3-furan-3(2H)-ylidene)indolin-2-ones were successfully prepared depending upon the structures of the pyridinium salts and reaction conditions. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were briefly discussed.