Solid-Phase Synthesis of Bis(guanidines) Based on an Aza Wittig/Carbodiimide-Mediated Annulation Process

Pablo López-Cremades; Pedro Molina; Enrique Aller; Angeles Lorenzo

doi:10.1055/s-2000-7635

Synlett 2000; 2000(10): 1411-1414
DOI: 10.1055/s-2000-7635

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Solid-Phase Synthesis of Bis(guanidines) Based on an Aza Wittig/Carbodiimide-Mediated Annulation Process

Pablo López-Cremades^* , Pedro Molina, Enrique Aller, Angeles Lorenzo

^*Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30071, Murcia, Spain; Fax + 34 968 364 149; E-mail: pmolina@um.es

Abstract

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An efficient solid-phase synthetic method towards bis(guanidines) is reported via aza Wittig coupling of a solid-supported bis(iminophosphorane) with an aromatic isothiocyanate to generate the corresponding solid-supported iminophosphorane, which upon exposure to a second aromatic isothiocyanate underwent aza Wittig/intramolecular cyclization and simultaneous cleavage to give the desired bis(guanidines).

bis(guanidines) - iminophosphoranes - solid-phase synthesis - combinatorial chemistry - aza Wittig reaction

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