2-{8 {60 -Alkoxy-arylmethyl{9 -2-imidazolines and -1,4,5,6-tetrahydropyrimidines

Abstract

Abstract 2-( Alpha -(Lower-alkoxy)- Alpha -R1-Ar-methyl)-2-imidazolines, -1,4,5,6-tetrahydropyrimidines and -4,5,6,7-tetrahydro-1H-1,3diazepines, having pharmacological properties, e.g., hypoglycemic, diuretic, anti-inflammatory, are prepared by heating a 2-(lower-alkoxy)-2-Ar-alkanenitrile with an alkanediamine, wherein 2, 3 or 4 carbon atoms respectively intervene between the two amino groups, in the presence of a catalytic amount of carbon disulfide or hydrogen sulfide, where R1 is hydrogen, lower-alkyl or lower-alkenyl, Ar is phenyl, naphthyl, indanyl, biphenylyl, cyclohexenyl, cyclohexyl and phenyl substituted by from one to three substituents selected from lower-alkyl, lower-alkoxy, halo, trihalomethyl, loweralkylmercapto, lower-alkylsulfonyl, di-(lower-alkyl)amino, amino, hydroxy, nitro, hydroxyamino and benzyloxy. The intermediate 2(lower-alkoxy)-2-Ar-alkanenitriles are prepared preferably by first reacting an aldehyde of the formula Ar-CHO with a tri(lower-alkyl) orthoformate to form the aldehyde di-(lower-alkyl) acetal, reacting the latter with an acyl halide to form the corresponding Alpha -halo-Ar-methyl lower-alkyl ether and reacting said ether with an alkali cyanide to yield said intermediate nitrile.

Inventors

• 👤 Denis M Bailey

Bibliographic Details