1,2-Disubstituted Hexahydro-1H-benzo[d]imidazoles: Synthesis, Characterization, and Stability

Abstract

Starting from commercially available (hetero)aromatic nitriles and (1R,2R)-cyclohexane-1,2-diamine, nine NH-imidazolines (hexahydro-1H-benzo[d]imidazoles) were synthesized in good yields. The molecular structures of three imidazolines were confirmed by X-ray analysis. N-Benzylation afforded some of the desired N-benzylimidazolines, but was incompatible with imidazolines that possessed strong electron-accepting heteroaromatic groups at C2. In the latter cases, the products decomposed during column chromatography to form N,N′-disubstituted cyclohexane-1,2-diamines.

Key words

heterocycles - imidazolines - chiral pool - N-benzylation - stability

References

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CCDC 775750, CCDC 775752, and CCDC 775751 contain the supplementary crystallographic data of compounds 8, 11, and 12, respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone];
E-mail: [e-mail]].