Synthesis of acetyl deoxyvasicinone analogues from 2-(4-oxopentyl)quinazolin-4(3H)-ones via linear cyclizations

Abstract

Two deoxyvasicinone analogues were obtained from 2-(4-oxopentyl)quinazolin-4(3H)-ones via different process of linear cyclizations. The first was 1-acetyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one analogue derived from direct cyclization in the presence of I2 in basic condition. The other was 1-acetylpyrrolo[2,1-b]quinazolin-9(3H)-one analogue obtained from two-step procedures beginning with geminal dichlorination in acidic condition, followed by intramolecular CN bond formation in the presence of para-toluenesulfonic acid.