The first 4-dialkylamino-1,2-dihydropyridine derivatives: synthesis and basic reactions

Abstract

The first two 4-dialkylamino-1,2-dihydropyridine derivatives 4a and 4b are prepared in good yield by addition of n-butyllithium or t-butyllithium to 4-dimethylaminopyridine 1 followed by quench with diethylcarbonate. Compound 4a can be hydrolyzed under mild conditions providing 4-dihydropyridone 5, an interesting acceptor building block. On the other hand reaction of 4a with dimethyl acetylene dicarboxylate gives benzene derivative 7 via a cycloaddition-cycloreversion path.