Highly efficient four-component synthesis of 4(3H)-quinazolinones: Palladium-catalyzed carbonylative coupling reactions

Lin He, Haoquan Li, Helfried Neumann, Matthias Beller, Xiao Feng Wu

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83 Scopus citations

Abstract

Given the importance of quinazolinones and carbonylative transformations, a palladium-catalyzed fourcomponent carbonylative coupling system for the synthesis of diverse 4(3H)-quinazolinone in a concise and convergent fashion has been developed. Starting from 2-bromoanilines (1 mmol), trimethyl orthoformate (2 mmol), and amines (1.1 mmol), under 10 bar of CO, the desired products were isolated in good yields in the presence of Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%) in 1,4-dioxane (2 mL) at 1008C, using N,Ndiisopropylethylamine (2 mmol) as the base. Notably, the process tolerates the presence of various reactive functional groups and is very selective for quinazolinones, and was used in the synthesis of the precursor to the bioactive dihydrorutaempine.

Original languageEnglish
Pages (from-to)1420-1424
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume53
Issue number5
DOIs
StatePublished - 27 Jan 2014
Externally publishedYes

Keywords

  • Heterocycles
  • Multicomponent reactions
  • Palladium
  • Synthesis design
  • Synthetic methods

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