SYNTHESIS OF 1-FUNCTIONAL SUBSTITUTED PYRROLO[1,2-a]QUINAZOLINE-5(1H)-ONE DERIVATIVES
DOI:
https://doi.org/10.15407/dopovidi2023.03.060Keywords:
quinazolinones, pyrroloquinazolinones, reduction, nucleophilic substitution, functional derivativesAbstract
A convenient synthetic method for the preparation of 1-(iodomethyl)-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-ones has been developed. This method involves the selective reduction of 1-iodomethylpyrroloquinazolinium iodides using sodium borohydride. The targeted modification of the iodomethyl moiety of 1-(iodomethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones with S- and N-containing nucleophilic reagents has been demonstrated, leading to the synthesis of derivatives with thioacetate and azide functional groups. Hydrogenation of the latter compounds using 10% Pd/C catalyst yielded promising synthetic building blocks, namely, 1-(aminomethyl)pyrrolo[1,2-a]quinazolin-5(1H)-ones. Furthermore, the behavior of 1-(iodomethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones in the presence of ammonia was investigated, which resulted in the cleavage of the C-N bond of the pyrrolidine ring and the formation of 2-(3-oxobutyl)quinazolin-4(3H)-ones, displaying chain-ring tautomeric behavior.
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