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

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 ana-logue derived from direct cyclization in the presence of I2 in basic condition. The other was 1-acetylpyr-rolo[2,1-b]quinazolin-9(3H)-one analogue obtained from two-step procedures beginning with geminal dichlorination in acidic condition, followed by intramolecular C-N bond formation in the presence of para-toluenesulfonic acid.CO 2023 Elsevier Ltd. All rights reserved.

Automated summary

Two deoxyvasicinone analogues were synthesized via different linear cyclization processes from 2-(4-oxopentyl)quinazolin-4(3H)-ones. The first analogue, 1-acetyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one, was obtained through direct cyclization with I2 in basic conditions. The second analogue, 1-acetylpyrrolo[2,1-b]quinazolin-9(3H)-one, was synthesized via a two-step procedure involving geminal dichlorination in acidic conditions followed by intramolecular C-N bond formation in the presence of para-toluenesulfonic acid.