Copper and manganese co-mediated cascade aza-Michael addition/cyclization and azidation of 1,3-enynes: regioselective synthesis of fully substituted azido pyrroles

An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN 3 ) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-11, Vol.18 (43), p.898-8915
Hauptverfasser: Ge, Junying, Ding, Qiuping, Yang, Man, He, Tian, Peng, Yiyuan
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Sprache:eng
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Zusammenfassung:An efficient Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide (TMSN 3 ) for the synthesis of fully substituted azido pyrroles has been developed. The three-component reaction has the characteristics of high regioselectivity, wide substrate scope, and mild reaction conditions. A preliminary mechanism for this transformation is proposed. A Cu and Mn co-mediated aerobic oxidative cyclization and azidation reaction of 1,3-enynes with amines and trimethylsilyl azide has been developed to synthesize fully substituted azido pyrroles.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01927e