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Synthesis of diverse dihydropyrimidine-related scaffolds by fluorous benzaldehyde-based Biginelli reaction and post-condensation modifications

  • University of Massachusetts Boston

Research output: Contribution to journal › Article › peer-review

Abstract

Dihydropyrimidinones and dihydropyrimidinethiones generated from the Biginelli reactions of perfluorooctanesulfonyl-attached benzaldehydes are used as common intermediates for post-condensation modifications such as cycloaddition, Liebeskind-Srogl reaction and Suzuki coupling to form biaryl-substituted dihydropyrimidinone, dihydropyrimidine, and thiazolopyrimidine compounds. The high efficiency of the diversity-oriented synthesis is achieved by conducting a multicomponent reaction for improved atom economy, under microwave heating for fast reaction, and with fluorous solid-phase extractions (F-SPE) for ease of purification.

Original languageEnglish
Article number150
Pages (from-to)1294-1298
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume7
DOIs
StatePublished - Sep 16 2011

ASJC Scopus Subject Areas

  • Organic Chemistry

Keywords

  • Biginelli reaction
  • Dihydropyrimidine
  • Diversity-oriented synthesis
  • Fluorous
  • Suzuki coupling

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