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Synlett 2001; 2001(2): 0218-0221
DOI: 10.1055/s-2001-10767
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Microwave-assisted Regioselective Synthesis of 2,4-Disubstituted Imidazoles: Nortopsentin D Synthesized by Minimal Effort

Pilar M. Fresneda* , Pedro Molina, Miguel A. Sanz
  • *Departamento de Química Orgánica, Facultad de Química. Universidad de Murcia, Campus de Espinardo, 30071, Murcia, Spain; Fax +34 968 364149; E-mail: pmolina§um.es; fresneda§fcu.um.es
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Publication Date:
31 December 2001 (online)

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A two step regioselective synthesis of 2,4-disubstituted imidazoles based on the reaction of α-azidoacetyl indoles with carboxylic acids in the presence of tertiary phosphines followed by cyclization of the resulting ketoamides by the action of ammonium acetate under microwave irradiation is described. The method has successfully been applied to the synthesis of the antifungal nortopsentin D [2,4-bis(3-indolyl)imidazole].

nortopsentin - 2,4-disubstituted imidazoles - microwave chemistry - tertiary phosphines