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Report | Regular issue | Vol 23, No. 1, 1985, pp.93-98
Published online, 1st January, 1970
DOI: 10.3987/R-1985-01-0093
Synthesis of Heterocyclic Compounds. XLV. Synthetic Studies Using 2,3-Substituted Propenenitriles: Synthesis of 2-Amino-6-ethylthiopyridines and 3,4-Dihydropyridines

Luis Fuentes,* Juan José Vaquero, Juan Carlos del Castillo, María Isabel Ardid, and José Luis Soto

*Departamento de Química Orgánica, Universidad de Alcalá de Henares, 28871 Alcalá de Henares (Madrid), Spain

Abstract

The reactions of malononitrile and arylmethylmalononitriles in alcohols-sodium ethanothiolate with 3-aryl-2-cyanopropenenitriles (1) are studied as a method of synthesis of 2-amino-4-aryl-3,5-dicyano-6-ethylthiopyridines (2) and 2-amino-4-aryl-3-arylmethyl-3,5-dicyano-6-ethylthio-3,4-dihydropyridines (3) respectively. Compounds 3 are isolated as a mixture of diastereoisomers, here designated as α and β. The structure of the 3a(β) isomer (Ar1=Ar2=Ph) has been determined by X-Ray crystallography. Pyridines 4 were obtained by hydrogen cyanide elimination from dihydropyridines 3.