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Paper | Regular issue | Vol 63, No. 11, 2004, pp.2557-2572
Published online, 8th October, 2004
DOI: 10.3987/COM-04-10191
1-Aryl-3-alkyl-1,4,5,6-tetrahydropyrimidinium Salts. Part 2. Reactions with Nucleophiles

María B. García, Mariana Zani, Isabel A. Perillo, and Liliana R. Orelli*

*Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113) Buenos Aires, Argentina

Abstract

The reactivity of 1-aryl-3-alkyl-1,4,5,6-tetrahydropyrimidinium salts (1) towards nucleophiles was studied. Hydrolysis of salts (1) afforded initially compounds (2, kinetic products) through the corresponding amidinium hydroxides (4). The regioselectivity of the reaction was analyzed considering the relative leaving group abilities and the stereoelectronic control theory. Amino amides (2a-c) in the reaction medium underwent spontaneous formyl migration, affording compounds (3, thermodynamic products). Reduction of salts (1) with sodium borohydride led to acyclic trimethylenediamines (5) or to the corresponding hexahydropyrimidines (6), according to the reaction conditions. Aminolysis of compound (1f) with isopropylamine yielded an acyclic formamidine (7f).