Resnyanskaya E. Hetarylacetonitriles and their derivatives in synthesis of fused pyrrolopyrimidines

The interaction of 2-hetaryl-3-oxo-4-chlorobuty-ronitriles and arylaminoacids or their hetero analogues was investigated, leading to formation of hetarylsubstituted pyrrolo[1,2-a]quinazoline-2,5-diones and pyrrolo[1,2-a]thieno[3,2-e]pyrimidine-4,7-diones. The alkylation of hetarylacetonitriles by chloroacetamides was studied, resulting in 5-amino-4-(2-benzothiazolyl)-1,2-dihydro-2-oxopyrroles and pyrrolo[1,2-a]quinazoline-1,5-dione. An unexpected transformation, yielding 1,3-bis-hetaryl-2-amino-4-oxocyclopentenones was found.The regioselective heteroannelation in 2-(4-oxo-3,4-dihydro-2-quinazolinyl)acetonitriles was found, leading to 2,5-dioxo-1,2,4,5-tetrahydropyrrolo[1,2-a]quinazoline-3-carbonitriles. А facile route to the 2 novel heterocyclic systems was elaborated.