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Bismuth (III) Chloride Catalyzed Multicomponent Synthesis of Substituted Hexahydroimidazo[1, 2-<i>a</i>]Pyridines
Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
Centre for Applied Chemistry, School of Applied Material Sciences, Central University of Gujarat, Gandhinagar, India
Centre for Applied Chemistry, School of Applied Material Sciences, Central University of Gujarat, Gandhinagar, India
Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
- 1 Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
- 2 Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
- 3 Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
- 4 Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
- 5 Centre for Applied Chemistry, School of Applied Material Sciences, Central University of Gujarat, Gandhinagar, India
- 6 Centre for Applied Chemistry, School of Applied Material Sciences, Central University of Gujarat, Gandhinagar, India
- 7 Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, IL, USA
Green and Sustainable Chemistry·Volume 11 (2021)·Pages 89–95·Published 30 July 2021·DOI10.4236/gsc.2021.113008
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Abstract
The synthesis of nitrogen containing heterocycles is of particular interest in the pharmaceutical industry due to the range of biological activities exhibited by such compounds. Their synthesis using multicomponent reactions saves steps and minimizes waste generation. The bismuth (III) chloride multicomponent synthesis of a series of hexahydroimidazo[1, 2- <i> a </i> ]pyridines is reported. Bismuth (III) compounds are especially attractive from a green chemistry perspective because they are remarkably nontoxic, non-corrosive and relatively inexpensive. The reported method avoids chromatography and an aqueous waste stream to afford the products in a very mass efficient manner.
KeywordsBismuth ChlorideGreen ChemistryHeterocyclesMulticomponent Reactions
- Cabrele, C. and Reiser, O. (2016) The Modern Face of Synthetic Heterocyclic Chemistry. The Journal of Organic Chemistry, 81, 10109-10125. https://doi.org/10.1021/acs.joc.6b02034
- Taylor, A.P., Robinson, R.P., Fobian, Y.M., Blakemore, D.C., Jones, L.H. and Fadeyi, O. (2016) Modern Advances in Heterocyclic Chemistry in Drug Discovery. Organic & Biomolecular Chemistry, 14, 6611-6637. https://doi.org/10.1039/C6OB00936K
- Kerru, N., Gummidi, L., Maddila, S., Gangu, K.K. and Jonnalagadda, S.B. (2020) A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications. Molecules, 25, 1909. https://doi.org/10.3390/molecules25081909
- Hanson, S.M., Morlock, E.V., Satyshur, K.A. and Czajkowski, C. (2008) Structural Requirements for Eszopiclone and Zolpidem Binding to the GABAA Receptor Are Different. Journal of Medicinal Chemistry, 51, 7243-7252. https://doi.org/10.1021/jm800889m
- Enguehard-Gueiffier, C. and Gueiffier, A. (2007) Recent Progress in the Pharmacology of Imidazo[1,2-a]pyridines. Mini-Reviews in Medicinal Chemistry, 7, 888-899. https://doi.org/10.2174/138955707781662645
- Yan, R., Yan, H., Ma, C., et al. (2012) Cu(I)-Catalyzed Synthesis of Imidazo[1,2-a]pyridines from Aminopyridines and Nitroolefins Using Air as the Oxidant. Journal of Organic Chemistry, 77, 2024-2028. https://doi.org/10.1021/jo202447p
- Stasyuk, A.J., Banasiewicz, M., Cyrański, M.K. and Gryko, D.T. (2012) Imidazo[1,2-a]pyridines Susceptible to Excited State Intramolecular Proton Transfer: One-Pot Synthesis via an Ortoleva-King Reaction. Journal of Organic Chemistry, 77, 5552-5558. https://doi.org/10.1021/jo300643w
- Cai, Z., Wang, S. and Ji, S. (2013) Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines. Advanced Synthesis & Catalysis, 355, 2686-2692. https://doi.org/10.1002/adsc.201300333
- Monir, K., Bagdi, A.K., Ghosh, M. and Hajra, A. (2014) Unprecedented Catalytic Activity of Fe(NO3)3·9H2O: Regioselective Synthesis of 2-Nitroimidazopyridines via Oxidative Amination. Organic Letters, 16, 4630-4633. https://doi.org/10.1021/ol502218u
- Bagdi, A.K., Rahman, M., Santra, S., Majee, A. and Hajra, A. (2013) Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale. Advanced Synthesis & Catalysis, 355, 1741-1747. https://doi.org/10.1002/adsc.201300298