Isocyanide Addition to Pyridinium Salts. Efficient Entry into Substituted Nicotinonitrile Derivatives

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作者：Nana Aba O. Williams ; Carme Masdeu ; José ; Luis Dí ; az ; Rodolfo Lavilla
刊名：Organic Letters
出版年：2006
出版时间：December 7, 2006
年：2006
卷：8
期：25
页码：5789 - 5792
全文大小：82K
年卷期：v.8,no.25(December 7, 2006)
ISSN：1523-7052

文摘

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The addition of isocyanides to pyridinium salts is studied. The process takes place efficiently when a carboxamido group is present in the 3position of the pyridine ring. The outcome of the reaction involves the stabilization of the nitrilium intermediate by the amide, which suffersa mild dehydration, leading regioselectively to

-cyano-

-carbamoyl-1,4-dihydropyridines. In this way, a variety of nicotinamide derivativeswere carbamoylated. Extension to quinolinium, isoquinolinium, and N-acylpyridinium salts is also reported.

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