One-pot synthesis of novel 2-oxo(2H)-spiro[benzofuran-3,3′-pyrrolines] via 1,4-dipolar cycloaddition reaction

An efficient synthesis of novel spiro[2-oxobenzofuran-3,3′-pyrrolines] is achieved via a three-component 1,4-dipolar cycloaddition reaction at rt involving benzofuran-2,3-diones, dimethyl acetylenedicarboxylate along with imidazo[1,5-a]pyridine, or imidazo[1,5-a]quinoline or imidazo[5,1-a]isoquinoli...

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Published in:Results in Chemistry 2022-01, Vol.4, p.100643, Article 100643
Main Authors: Al-Mahadeen, Mohammed M., Zahra, Jalal A., El-Abadelah, Mustafa M., Jaber, Areej M., Khanfar, Monther A.
Format: Article
Language:English
Subjects:
Benzofuran-2,3-diones
Dimethyl acetylenedicarboxylate
N-Bridgehead imidazo-heterocycles
Spiro cycloadducts
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creator Al-Mahadeen, Mohammed M.
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description An efficient synthesis of novel spiro[2-oxobenzofuran-3,3′-pyrrolines] is achieved via a three-component 1,4-dipolar cycloaddition reaction at rt involving benzofuran-2,3-diones, dimethyl acetylenedicarboxylate along with imidazo[1,5-a]pyridine, or imidazo[1,5-a]quinoline or imidazo[5,1-a]isoquinoline. The expected isomeric benzofuro[3,2-f]oxazepines (kinetic control cycloadducts) were, however, not detected. Structures of the title spiro products are evidenced from HRMS and NMR spectral data and further confirmed by single-crystal X-ray crystallography.
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subjects Benzofuran-2,3-diones
Dimethyl acetylenedicarboxylate
N-Bridgehead imidazo-heterocycles
Spiro cycloadducts
title One-pot synthesis of novel 2-oxo(2H)-spiro[benzofuran-3,3′-pyrrolines] via 1,4-dipolar cycloaddition reaction
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