Synthesis of pyrimido[2, 1-a]isoindolone and isoindolo[2, 1-a]quinazolinone via intramolecular aza-Prins type reaction. Issue 88 (25th October 2021)

• Record Type: Journal Article
• Authors: Biswas, Subhamoy; Porashar, Bikoshita; Arandhara, Pallav Jyoti; Saikia, Anil K.
• Is Part Of: Chemical communications. Volume 57:Issue 88(2021)
• Page Start: 11701
• Page End: 11704
• Publication Date: 2021-10-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc04554g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient approach for the synthesis of pyrimido[2, 1- a ]isoindolone and isoindolo[2, 1- a ]quinazolinone via intramolecular aza-Prins type reaction of N -acyliminium ions and amides in excellent yields is reported. 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, 6 a -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(9 a 1 H )-dione and carbonyl derivatives.