Di-π-methane rearrangement of 4-heteroaryl-1,4(or 3,4)-dihydropyrimidines

Abstract

Several 4-R-1,4(or 3,4)-dihydropyrimidines (R = 2- or 3-thienyl, 2-furyl, 1-methylpyrrol-2-yl, and 3-pyridyl), containing heteroaryl vinyl methane units were shown to undergo photochemical rearrangement into 5-R-1,2(or 2,3)-dihydropyrimidines. These compounds were oxidized to yield 5-heteroarylpyrimidines. The chemical yields of the photorearrangement were found to be strongly dependent on the nature of the heteroaryl group.