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Synthesis of imidazo[1,2-a]pyridines via multicomponent GBBR using a-isocyanoacetamides
1 , 2 , * 1
1  Universidad de Guanajuato, División de Ciencias Naturales y Exactas, Departamento de Química
2  Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico


Abstract: A series of new six novel imidazo[1,2-a]pyridines were synthesized by Groebke-Blackburn-Bienaymé reactions (GBBRs) by employing ammonium chloride (10 mol%) as a catalyst in moderate to good yields (76–44%) using 2-isocyano-1-morpholino-3-phenylpropan- 1-one. This is the first successful use of this type of a-isocyanoacetamide in a GBBR, as these reactive isonitriles readily undergo ring-chain tautomerization, as reported in other IMCR (isonitrile-based multicomponent reactions). The product structures contain a peptidomimetic imidazo[1,2-a]pyridine scaffold linked to an a-aminomorpholide and are of interest to medicinal chemists.

Keywords: Multicomponent reactions; imidazo[1,2-a]pyridine; GBBR; a-isocyanoacetamides.