New Entry to a Three-Component Pyrimidine Synthesis by TMS−Ynones via Sonogashira Coupling
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- 21 August 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (19) , 3451-3454
- https://doi.org/10.1021/ol035212q
Abstract
TMS−ynones are versatile synthetic equivalents of β-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.Keywords
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