Literature DB >> 17253825

Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot.

Erin F Dimauro1, Joseph M Kennedy.   

Abstract

The rapid and efficient synthesis of various 2,6-disubstituted-3-amino-imidazopyridines using a microwave-assisted one-pot cyclization/Suzuki coupling approach is described. The utility of a 2-aminopyridine-5-boronic acid pinacol ester as a robust and versatile building block for the synthesis of diverse compound libraries is emphasized. The boronate functional group is remarkably tolerant to the Lewis acid catalyzed cyclizations, and the subsequent Pd(0)-catalyzed Suzuki coupling reactions proceed cleanly in the presence of magnesium salts. This work highlights the vast potential of microwave-assisted, metal-catalyzed, multicomponent reactions.

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Year:  2007        PMID: 17253825     DOI: 10.1021/jo0622072

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 in total

1.  Facile microwave-assisted synthesis of benzimidazole scaffolds via Ugi-type three-component condensation (3CC) reactions.

Authors:  Gui-Ting Song; Zhi-Gang Xu; Dian-Yong Tang; Shi-Qiang Li; Zhi-Gang Xie; Hong-Liang Zhong; Zhi-Wei Yang; Jin Zhu; Jin Zhang; Zhong-Zhu Chen
Journal:  Mol Divers       Date:  2015-11-18       Impact factor: 2.943

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

Review 3.  Emerging approaches for the syntheses of bicyclic imidazo[1,2-x]-heterocycles.

Authors:  Christopher Hulme; Yeon-Sun Lee
Journal:  Mol Divers       Date:  2008-04-12       Impact factor: 2.943

4.  General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: one-pot synthesis of alpidem and zolpidem.

Authors:  Natalia Chernyak; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

5.  One-pot synthesis of 2-phenylimidazo[1,2-α]pyridines from acetophenone, [Bmim]Br(3) and 2-aminopyridine under solvent-free conditions.

Authors:  Zhang-Gao Le; Zong-Bo Xie; Jian-Ping Xu
Journal:  Molecules       Date:  2012-11-09       Impact factor: 4.411

Review 6.  Groebke-Blackburn-Bienaymé multicomponent reaction: emerging chemistry for drug discovery.

Authors:  Saad Shaaban; Bakr F Abdel-Wahab
Journal:  Mol Divers       Date:  2015-05-28       Impact factor: 2.943

7.  Catalyst free, C-3 functionalization of imidazo[1,2-a]pyridines to rapidly access new chemical space for drug discovery efforts.

Authors:  Naresh Gunaganti; Anupreet Kharbanda; Naga Rajiv Lakkaniga; Lingtian Zhang; Rose Cooper; Hong-Yu Li; Brendan Frett
Journal:  Chem Commun (Camb)       Date:  2018-11-15       Impact factor: 6.222

8.  Gold Catalysed Redox Synthesis of Imidazo[1,2-a]pyridine using Pyridine N-Oxide and Alkynes.

Authors:  Eric P A Talbot; Melodie Richardson; Jeffrey M McKenna; F Dean Toste
Journal:  Adv Synth Catal       Date:  2014-03-10       Impact factor: 5.837

Review 9.  Microwave multicomponent synthesis.

Authors:  Helmut M Hügel
Journal:  Molecules       Date:  2009-12-01       Impact factor: 4.411

10.  Iodine Promoted Efficient Synthesis of 2-Arylimidazo[1,2-a]pyridines in Aqueous Media: A Comparative Study between Micellar Catalysis and an "On-Water" Platform.

Authors:  Zigmee T Bhutia; Padmini C Panjikar; Shruti Iyer; Amrita Chatterjee; Mainak Banerjee
Journal:  ACS Omega       Date:  2020-05-26
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