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Synthesis and properties of 1-aryl-2-alkyl-1,4,5,6-tetrahydropyrimidines

✍ Scribed by Liliana R. Orelli; Fernando Niemevz; María B. García; Isabel A. Perillo

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
543 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A general method is described for the synthesis of 1‐aryl‐2‐alkyl‐1,4,5,6‐tetrahydropyrimidines 1, by cyclization of N‐acyl‐N′‐aryltrimethylenediamines 2 with trimethylsilyl polyphosphate. Precursors 2 were obtained by aminolysis of the corresponding N‐(3‐bromopropyl)amides 3. The ^1^H nmr spectra of tetrahydropyrimidines 1 are analyzed, discussing the influence of substituents in positions 1 and 2 of the heterocyclic ring. Alkaline hydrolysis of compounds 1, which originates exclusively N‐acyl‐N′‐aryltrimethylenediamines 2, through an intermediate carbinolamine, was also studied. Cleavage of such an intermediate is discussed in the light of the stereoelectronic control theory. Reduction of compounds 1 with borane, leads regiospecifically to N‐alkyl‐N′‐aryltrimethylenediamines 6.

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