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Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinone via intramolecular aza-Prins type reaction†
Abstract
A novel aza-Prins type cyclization reaction involving N-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis of N-heterocyclic frameworks. Further, post-synthetic modification results in the unprecedented formation of its triazole, tetracyclic diazacyclopenta[def]phenanthrene-1,4(9a1H)-dione and carbonyl derivatives.
![Graphical abstract: Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinone via intramolecular aza-Prins type reaction](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D1CC04554G&imageInfo.ImageIdentifier.Year=2021)
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