Catalytic alkynone generation by Sonogashira reaction and its application in three-component pyrimidine synthesis.
The Sonogashira alkynylation of acid chlorides can be efficiently conducted in less than an hour by performing the reaction in tetrahydrofuran as a solvent and in the presence of one stoichiometrically necessary equivalent of triethylamine as a base. This approach also opens new avenues for consecutive one-pot multicomponent reactions. As an example, the one-pot three-component pyrimidine synthesis illustrates the versatility of this modified Sonogashira protocol as an entry to diversity-oriented heterocycle synthesis in a one-pot fashion. The protocol can be completed within a few hours.
D'Souza
Daniel M
DM
School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, UK.
Müller
Thomas J J
TJ
D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003300:Copper; D005021:Ethylamines / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium; D011743:Pyrimidines / Q000138:chemical synthesis*
D002712:Chlorides; D005021:Ethylamines; D011743:Pyrimidines; D010165:Palladium; D003300:Copper; C016162:triethylamine