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Keywords = α-isocyanoacetamides

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10 pages, 1145 KiB  
Proceeding Paper
Synthesis of Imidazo[1,2-a]pyridines via Multicomponent GBBR Using α-isocyanoacetamides
by Manuel A. Rentería Gómez, Alejandro Islas-Jácome and Rocío Gámez-Montaño
Proceedings 2019, 9(1), 53; https://doi.org/10.3390/ecsoc-22-05692 - 14 Nov 2018
Cited by 2 | Viewed by 1852
Abstract
Six novel imidazo[1,2-a]pyridines were synthesized by Groebke–Blackburn–Bienaymé reactions (GBBRs) under eco-friendly conditions (10 mol% ammonium chloride catalyst in EtOH at room temperature) with 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 α-isocyanoacetamide [...] Read more.
Six novel imidazo[1,2-a]pyridines were synthesized by Groebke–Blackburn–Bienaymé reactions (GBBRs) under eco-friendly conditions (10 mol% ammonium chloride catalyst in EtOH at room temperature) with 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 α-isocyanoacetamide in a GBBR, as these reactive isonitriles readily undergo ring-chain tautomerization, as reported in other IMCRs (isonitrile-based multicomponent reactions). The product structures contain a peptidomimetic imidazo[1,2-a]pyridine scaffold linked to an α-aminomorpholide and are of interest to medicinal chemists. Full article
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