4.8 Article

New entry to a three-component pyrimidine synthesis by TMS-ynones via Sonogashira coupling

Journal

ORGANIC LETTERS
Volume 5, Issue 19, Pages 3451-3454

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol035212q

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TMS-ynones are versatile synthetic equivalents of beta-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides and (TMS)-acetylene with only one equiv (!) of triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition-cyclocondensation sequence.

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