Convenient Syntheses of Unsymmetrical Imidazolidines

Unsymmetrical imidazolidines 10 − 14, optically active imidazolidines 20 − 22, and 2,3-dihydro-1H-benzimidazoles 28 and 29 were synthesized in good to excellent yields by Mannich reactions of 1,2-ethanediamines 8a − c, 18a − c, or N-methyl-1,2-benzenediamine (26a) with benzotriazole and formaldehyde...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (9), p.3109-3114
Main Authors: Katritzky, Alan R, Suzuki, Kazuyuki, He, Hai-Ying
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:Unsymmetrical imidazolidines 10 − 14, optically active imidazolidines 20 − 22, and 2,3-dihydro-1H-benzimidazoles 28 and 29 were synthesized in good to excellent yields by Mannich reactions of 1,2-ethanediamines 8a − c, 18a − c, or N-methyl-1,2-benzenediamine (26a) with benzotriazole and formaldehyde, followed by the nucleophilic substitution of the benzotriazolyl group with C-nucleophiles (Grignard reagents, sodium cyanide), an S-nucleophile (benzenethiol), and a P-nucleophile (triethyl phosphite).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010868n