Direct synthesis of 2-oxo-acetamidines from methyl ketones, aromatic amines and DMF via copper-catalyzed C(sp(3))–H amidination

A convenient method for the synthesis of 2-oxo-acetamidines from methyl ketones using aromatic amines and DMF as nitrogen sources is reported via copper-catalyzed C(sp(3))–H amidination. Various methyl ketones react readily with aromatic amines and DMF, producing 2-oxo-acetamidines in yields of 47 t...

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Detalles Bibliográficos
Autores principales: Xie, Dianke, He, Wei, Xiao, Jiang, Wu, Yao, Guo, Yongjia, Liu, Qiang, Guo, Cancheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9061129/
https://www.ncbi.nlm.nih.gov/pubmed/35519951
http://dx.doi.org/10.1039/c9ra00616h
Descripción
Sumario:A convenient method for the synthesis of 2-oxo-acetamidines from methyl ketones using aromatic amines and DMF as nitrogen sources is reported via copper-catalyzed C(sp(3))–H amidination. Various methyl ketones react readily with aromatic amines and DMF, producing 2-oxo-acetamidines in yields of 47 to 92%. This protocol features the simultaneous formation of C–N and C[double bond, length as m-dash]N bonds using DMF and aromatic amines as two different nitrogen sources. It thus provides an efficient approach to construct acyclic amidines via three C(sp(3))–H bond amidination. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

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