Events The 22nd International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session C. General Organic Synthesis of the event The 22nd International Electronic Conference on Synthetic Organic Chemistry

Published date

14 Nov, 2018

Citation

Manuel A. Rentería Gómez, Rocío Gámez-Montaño, Alejandro Islas-Jácome, Synthesis of imidazo[1,2-a]pyridines via multicomponent GBBR using a-isocyanoacetamides, in Proceedings of The 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-22-05692

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Synthesis of imidazo[1,2-a]pyridines via multicomponent GBBR using a-isocyanoacetamides

Manuel A. Rentería Gómez ¹

Alejandro Islas-Jácome ²

Rocío Gámez-Montaño 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

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.

Manuscript

ECSOC 2018-10112018.pdf

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