Cu/Ag-Catalyzed Reaction of Azirines with Anthranils: Synthesis of (Quinazolin-2-yl)methanone Derivatives

A Cu/Ag-catalyzed annulation of 3-aryl-2H-azirines with anthranils has been developed to expedite syntheses of (quinazolin2-yl)­methanone derivatives. The transformation represents an unprecedented approach which employs a copper catalysis to cleave both a N–C2 azirine bond and N–O anthranil bond. S...

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Veröffentlicht in:Organic letters 2020-09, Vol.22 (17), p.6756-6759
Hauptverfasser: Sun, Yajun, Sun, Huimin, Wang, Ying, Xie, Fang
Format: Artikel
Sprache:eng
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Zusammenfassung:A Cu/Ag-catalyzed annulation of 3-aryl-2H-azirines with anthranils has been developed to expedite syntheses of (quinazolin2-yl)­methanone derivatives. The transformation represents an unprecedented approach which employs a copper catalysis to cleave both a N–C2 azirine bond and N–O anthranil bond. Subsequently, an unexplored 1,3-hydroxyl migration and β-N elimination are likely the key to access (quinazolin-2-yl)­methanone derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02222