4.6 Article

A silver catalyzed domino reaction of N-cyanamide alkenes and 1,3-dicarbonyls for the synthesis of quinazolinones

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 32, Pages 5899-5906

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01252k

Keywords

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Funding

  1. National Basic Research Program of China (973 Program) [2011CB710800]
  2. Hi-Tech Research and Development Program of China (863 Program) [2011AA02A209]

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A silver catalyzed domino reaction of N-cyanamide alkenes and 1,3-dicarbonyls including 1,3-diketones and ethyl acetoacetate has been developed for the facile synthesis of quinazolinones. In the presence of AgNO3/K2S2O8, the diketones could be converted to radicals and coupled with N-cyanamide alkenes to undergo a cyclization cascade for accessing quinazolinones. This method features mild reaction conditions, readily available starting materials, and valuable synthetic utility. Moreover, the products could be further transformed into various heterocycles.

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