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Paper | Special issue | Vol 39, No. 1, 1994, pp.139-153
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S(B)8
A Two-step Synthesis of Imidazoles from Aldehydes via 4-Tosyloxazolines

David A. Horne, Kenichi Yakusijin, and George Büchi*

*Department of Chemistry, Room 18-390, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, U.S.A.


Imidazoles with substituents in the 4- and 4,5-positions were prepared by heating 4-tosyloxazolines in saturated methanolic ammonia. Similar treatment of these oxazolines with monoalkylamines regioselectively affords 1,4-disubstituted imidazoles. When oxazolines bearing an ethyl group at the 4-position were heated with alkylamines, however, a regioisomeric mixture of di- or trisubstituted imidazoles was produced. These reactions proceed via an intermolecular condensation of α-amino ketones and amidines or intramolecular cyclization of α-amidino ketone intermediates, respectively.