Direct Synthesis of 3-Coumaranones with Calcium Carbide as an Acetylene Source
Rugang Fu, Yongzheng Lu, Guoren Yue, Dongqing Wu, Xu Li, Hai Song, Cheng Cao, Xinghai Yu, Yingxiao Zong
Abstract
A novel synthesis method for the construction of 3-coumaranones from the reaction of two molecules, calcium carbide and salicylaldehyde, was reported. Various 2-methyl-2-vinylbenzofuran-3(2H)-ones could be obtained in moderate yields in the absence of a metal catalyst. The salient features of this protocol involve widely available starting materials, an inexpensive and easy-to-handle alkyne source, and a cost-efficient route. The reaction mechanism was verified by density functional theory calculations of possible intermediates and corresponding transition states.
Topics & Concepts
AcetyleneChemistryCalcium carbideAlkyneCatalysisCombinatorial chemistrySalicylaldehydeDensity functional theoryMoleculeComputational chemistryCalciumOrganic chemistryPolymer chemistrySchiff baseSynthesis and Characterization of PyrrolesSynthesis of Organic CompoundsOxidative Organic Chemistry Reactions