4.8 Article

Synthesis of Pyrido[2,1-b]quinazolin-11-ones and Dipyrido[1,2a:2′,3′-d]pyrimidin-5-ones by Pd/DIBPP-Catalyzed Dearomatizing Carbonylation

Journal

ORGANIC LETTERS
Volume 17, Issue 6, Pages 1569-1572

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00452

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Funding

  1. Cytec Canada
  2. Natural Sciences and Engineering Research Council of Canada

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N-Fused heterocycles can be easily synthesized by palladium-catalyzed dearomatizing carbonylation using 1,3-bis(diisobutylphosphino)propane (DIBPP) as the ligand. Pyrido[2,1-b]quinazolin-11-ones were obtained from N-(2-bromophenyl)pyridine-2-amines in up to quantitative yield and dipyrido[1,2-a:2',3'-d]pyrimidin-5-ones from 3-bromo-N-(pyridine-2-yl)pyridine-2-amines in up to 84% yield. The cyclocarbonylation can be also realized without isolation of compound 1 and additional palladium catalyst.

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