A new methodology for the construction of methyl-substituted benzofuran rings from the reactions of calcium carbide with salicylaldehyde p-tosylhydrazones/2-hydroxyacetophenone p-tosylhydrazones is described. Various 2-methylbenzofurans and 2,3-dimethylbenzofurans could be obtained in satisfactory yield by using a cuprous chloride catalyst. The advantages of this protocol include the use of a readily available and easy-to-handle acetylene source and simple workup procedure.

A novel poly(4-vinylpyridine) supported acidic ionic liquid catalyst was synthesized by the reaction of 4-vinylpyridine with 1,3-propanesultone, followed by the polymerization and the addition of the heteropolyacid. Due to the combination of polymer features and ionic liquid, it acted as a heterogeneous catalyst to effectively catalyze the cyclocondensation reaction of anthranilamide with aldehydes under ultrasonic irradiation and afforded the corresponding 2,3-dihydro-4(1H)-quinazolinones compounds in good to excellent yields. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity. More importantly, the use of ultrasonic irradiation can obviously accelerate the reaction.

A new methodology for the direct synthesis of symmetric diarylethynes from the reactions of calcium carbide with arylboronic acids/esters is described. Various symmetric diarylethynes were generated from the corresponding arylboronic acids/esters in satisfactory yield by using a palladium catalyst. The advantages of this protocol include the use of a readily available and easy‐to‐handle acetylene source, and a simple work‐up procedure.

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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.