Regioselective four-component synthesis of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine and
Tooran Aghaalizadeh1, Farough Nasiri2
1Department of Applied Chemistry, University of Mohaghegh Ardabili, P.O. Box 56199-11367, Ardabil, Iran.
Abstract:
Four-component reaction between primary amines, dialkylacetylendicarboxylates, tetrazolo[1,5-a] quinoline-4-carbaldehyde and ethyl-2-cyanoacetate in the presence of 1,4-diaza-bicyclo[2.2.2]octane and zinc oxide nanoparticles results to the regioselective production of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine or pyridin-2(1H)-one derivatives in good to high yields. The selectivity of the catalyzed reaction toward the generation of the dihydropyridine or pyridin-2(1H)-one derivatives was found to be strongly dependent on the size of the alkyl groups in the ester moieties of the acetylenic esters. According to single-crystal X-ray diffraction and NMR studies, the pyridin-2(1H)-one derivatives involve a restricted rotation around the C-C bond connecting the tetrazoloquinoline and dihydropyridinone cyclic systems.
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