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Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion.


ABSTRACT: A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.

SUBMITTER: Collet JW 

PROVIDER: S-EPMC7011176 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion.

Collet Jurriën W JW   Morel Bénédicte B   Lin Hung-Chien HC   Roose Thomas R TR   Mampuys Pieter P   Orru Romano V A RVA   Ruijter Eelco E   Maes Bert U W BUW  

Organic letters 20200116 3


A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available <i>N</i>-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., <i>green</i> solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and <i>N</i>-uracil-amidines that are tolerated make this method an interesting alternative to  ...[more]

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