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      Recent Progress in Metal-Free Direct Synthesis of Imidazo[1,2- a]pyridines

      review-article
      ACS Omega
      American Chemical Society

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          Abstract

          This Mini-Review highlights the most effective protocols for metal-free direct synthesis of imidazo[1,2- a]pyridines, crucial target products and key intermediates, developed in the past decade. The emphases is given on the ecological impact of the methods and on the mechanistic aspects as well. The procedures efficiently applied in the preparation of important drugs and promising drug candidates are also underlined.

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          Most cited references71

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          Recent progress in the pharmacology of imidazo[1,2-a]pyridines.

          Imidazo[1,2-a]pyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. The paper deals with the recent progress realised in the comprehension of the pharmacological properties of this scaffold. From the many imidazo[1,2-a]pyridine analogues described in the literature, those discussed herein will be presented in three parts concerning first the enzyme inhibitors, then the receptor ligands and finally the anti-infectious agents.
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            Synthesis of imidazo[1,2-a]pyridines: a decade update

            Here we describe the various strategies for the synthesis of imidazo[1,2- a ]pyridines. Imidazopyridine is one of the important fused bicyclic 5–6 heterocycles and it is recognized as a “drug prejudice” scaffold due to its wide range of applications in medicinal chemistry. This moiety is also useful in material science because of its structural character. Synthesis of this moiety from the easily available chemicals is desirable due to its tremendous use in the various branches of chemistry. Here we report a review on the synthesis of this scaffold employing different strategies such as condensation, multicomponent reactions, oxidative coupling, tandem reactions, aminooxygenation, and hydroamination reactions.
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              The Groebke-Blackburn-Bienaymé Reaction : The Groebke-Blackburn-Bienaymé Reaction

              Imidazo[1,2-a]pyridine is a well-known scaffold in many marketed drugs, such as Zolpidem, Minodronic acid, Miroprofen and DS-1 and it also serves as a broadly applied pharmacophore in drug discovery. The scaffold revoked a wave of interest when Groebke, Blackburn and Bienaymé reported independently a new three component reaction resulting in compounds with the imidazo[1,2-a]-heterocycles as a core structure. During the course of two decades the Groebke Blackburn Bienaymé (GBB-3CR) reaction has emerged as a very important multicomponent reaction (MCR), resulting in over a hundred patents and a great number of publications in various fields of interest. Now two compounds derived from GBB-3CR chemistry received FDA approval. To celebrate the first 20 years of GBB-chemistry, we present an overview of the chemistry of the GBB-3CR, including an analysis of each of the three starting material classes, solvents and catalysts. Additionally, a list of patents and their applications and a more in-depth summary of the biological targets that were addressed, including structural biology analysis, is given.
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                Author and article information

                Journal
                ACS Omega
                ACS Omega
                ao
                acsodf
                ACS Omega
                American Chemical Society
                2470-1343
                14 December 2021
                28 December 2021
                : 6
                : 51
                : 35173-35185
                Affiliations
                [1]Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences , Acad. G. Bonchev str., bl. 9, 1113 Sofia, Bulgaria
                Author notes
                [* ]Email: vanya.kurteva@ 123456orgchm.bas.bg . Phone: +359 878940364.
                Author information
                https://orcid.org/0000-0001-8703-0066
                Article
                10.1021/acsomega.1c03476
                8717391
                34984250
                8fb6ae8e-782d-4e02-9b6f-8f4ab46f0a02
                © 2021 The Author. Published by American Chemical Society

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 02 July 2021
                : 30 November 2021
                Categories
                Mini-Review
                Custom metadata
                ao1c03476
                ao1c03476

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