Synthesis of 1-aryl-1,4,5,6-tetrahydropyrimidines and 1-aryl-3-substituted 1,4,5,6-tetrahydropyrimidinium salts

A synthetic approach to 1-aryl-1,4,5,6-tetrahydropyrimidines (1) is described, by ring closure of N-aryl-N'-formyl-1,3-propanediamines (5) with trimethylsilyl polyphosphate (PPSE). Quaternization of compounds (1) with methyl (or ethyl) iodide led to the corresponding cyclic amidinium salts (2),...

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Bibliographic Details
Published inHeterocycles Vol. 53; no. 11; pp. 2437 - 2451
Main Authors Orelli, LR, Garcia, MB, Perillo, IA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.11.2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
DESIGN
CYCLIZATIONS
MODELS
RECEPTOR AGONISTS
PPSE
NEUROCHEMICAL EVALUATION
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Summary:A synthetic approach to 1-aryl-1,4,5,6-tetrahydropyrimidines (1) is described, by ring closure of N-aryl-N'-formyl-1,3-propanediamines (5) with trimethylsilyl polyphosphate (PPSE). Quaternization of compounds (1) with methyl (or ethyl) iodide led to the corresponding cyclic amidinium salts (2), while treatment of compound (la) with 2,4-dinitrochlorobenzene yielded an open chain product resulting from hydrolysis of the salt. An alternative method was employed for the synthesis of 1-aryl-1,4,5,6-tetrahydropyrimidinium salts bearing a branched alkyl or an aryl substituent on N3, not accessible through alkylation. Such compounds were obtained in high yields by dehydrogenation of the corresponding hexahydropyrimidines (3). The scope and limitations of both procedures are discussed.
ISSN:0385-5414
DOI:10.3987/com-00-9018