Chemoselective synthesis of 5,4′-imidazolinyl spirobarbiturates NBS-promoted cyclization of unsaturated barbiturates and amidines

A selective cyclization of unsaturated barbiturates and amidines promoted by N -bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure a...

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Published inOrganic & biomolecular chemistry Vol. 19; no. 22; pp. 4978 - 4985
Main Authors Xu, Hui, Huang, Rong-Lu, Shu, Zhu, Hong, Ran, Zhang, Ze
Format Journal Article
Published 09.06.2021
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Summary:A selective cyclization of unsaturated barbiturates and amidines promoted by N -bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure and mild reaction conditions, providing a novel strategy for the highly selective and efficient construction of structurally diverse spiroimidazolines. The cyclization of unsaturated barbiturates and amidines promoted by N -bromosuccinimide furnished a variety of structurally novel 5,4′-imidazolinyl spirobarbiturates with high chemoselectivity, good yields and remarkable functional group tolerance.
Bibliography:Electronic supplementary information (ESI) available: NMR spectra. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/d1ob00508a
1982766
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00508a