Previous Article in event
Next Article in event
Next Article in session
Synthesis of imidazo[1,2-a]pyridines via multicomponent GBBR using a-isocyanoacetamides
Published:
14 November 2018
by MDPI
in The 22nd International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract:
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.