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Research Articles

New Methods for the Synthesis of 3-Aroylimidazo[1,2-a]Pyridines: A Review

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Pages 7673-7699 | Received 29 Aug 2022, Accepted 17 Oct 2022, Published online: 04 Nov 2022

References

  • C. Enguehard-Gueiffier and A. Gueiffier, “Recent Progress in the Pharmacology of Imidazo[1,2-a]Pyridines,” Mini Reviews in Medicinal Chemistry 7, no. 9 (2007): 888–99.
  • M. Hayakawa, H. Kaizawa, K.-I. Kawaguchi, N. Ishikawa, T. Koizumi, T. Ohishi, M. Yamano, M. Okada, M. Ohta, S.-I. Tsukamoto, et al, “Synthesis and Biological Evaluation of Imidazo[1,2-a]Pyridine Derivatives as Novel PI3 Kinase p110α Inhibitors,” Bioorganic & Medicinal Chemistry 15, no. 1 (2007): 403–12.
  • Z.A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir, and G. Revial, “Synthesis and Anticandidal Activity of Some Imidazopyridine Derivatives,” Journal of Enzyme Inhibition and Medicinal Chemistry 23, no. 6 (2008): 866–70.
  • L. Almirante, L. Polo, P. Rugarli, and A. Mugnaini, “Derivatives of Imidazole. I. Synthesis and Reactions of Imidazo[1,2-α]Pyridines with Analgesic, Antiinflammatory, Antipyretic, and Anticonvulsant Activity,” ACS Publications 8, no. 3 (1965): 305–12.
  • M. Lhassani, O. Chavignon, J.-M. Chezal, J.-C. Teulade, J.-P. Chapat, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, and A. Gueiffier, “Synthesis and Antiviral Activity of Imidazo [1, 2-a] Pyridines,” European Journal of Medicinal Chemistry 34, no. 3 (1999): 271–4.
  • A. Anaflous, N. Benchat, M. Mimouni, S. Abouricha, T. Ben-Hadda, B. El-Bali, A. Hakkou, and B. Hacht, “Armed Imidazo [1, 2-a] Pyrimidines (Pyridines): Evaluation of Antibacterial Activity,” Letters in Drug Design & Discovery 1, no. 3 (2004): 224–9.
  • T. Biftu, D. Feng, M. Fisher, G.-B. Liang, X. Qian, A. Scribner, R. Dennis, S. Lee, P.A. Liberator, C. Brown, et al, “Synthesis and SAR Studies of Very Potent Imidazopyridine Antiprotozoal Agents,” Bioorganic & Medicinal Chemistry Letters 16, no. 9 (2006): 2479–83.
  • J.J. Byrnes, D.J. Greenblatt, and L.G. Miller, “Benzodiazepine Receptor Binding of Nonbenzodiazepines in Vivo: Alpidem, Zolpidem and Zopiclone,” Brain Research Bulletin 29V., no. 6 (1992): 905–8.
  • H. Depoortere, B. Zivkovic, K.G. Lloyd, D.J. Sanger, G. Perrault, S.Z. Langer, and G. Bartholini, “Zolpidem, a Novel Nonbenzodiazepine Hypnotic. I. Neuropharmacological and Behavioral Effects,” The Journal of Pharmacology and Experimental Therapeutics 237, no. 2 (1986): 649–58.
  • S. Renard, A. Olivier, P. Granger, P. Avenet, D. Graham, M. Sevrin, P. George, and F. Besnard, “Structural Elements of the γ-Aminobutyric Acid Type a Receptor Conferring Subtype Selectivity for Benzodiazepine Site Ligands,” The Journal of Biological Chemistry 274, no. 19 (1999): 13370–4.
  • H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang, and Q. Zhu, “Copper-Catalyzed Intramolecular Dehydrogenative Aminooxygenation: Direct Access to Formyl-Substituted Aromatic N-Heterocycles,” Angewandte Chemie 123, no. 25 (2011): 5796–9.
  • T. Yuasa, M. Nogawa, S. Kimura, A. Yokota, K. Sato, H. Segawa, J. Kuroda, and T. Maekawa, “A Third-Generation Bisphosphonate, Minodronic Acid (YM529), Augments the Interferon a/B-Mediated Inhibition of Renal Cell Cancer Cell Growth Both in Vitro and in Vivo,” Clinical Cancer Research 11, no. 2 (2005): 853–9.
  • K. Mizushige, T. Ueda, H. Suzuki, and K. Yukiiri, “Olprinone: A Phosphodiesterase III Inhibitor with Positive Inotropic and Vasodilator Effects,” Cardiovascular Drug Reviews 20, no. 3 (2002): 163–74.
  • Y. Zhang, Z. Chen, W. Wu, Y. Zhang, and W. Su, “CuI-Catalyzed Aerobic Oxidative alpha-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles,” The Journal of Organic Chemistry 78, no. 24 (2013): 12494–504.
  • A.K. Bagdi, S. Santra, K. Monir, and A. Hajra, “Synthesis of Imidazo[1,2-a]Pyridines: A Decade Update,” Chemical Communications (Cambridge, England) 51, no. 9 (2015): 1555–75.
  • J. Koubachi, S.E. Kazzouli, M. Bousmina, and G. Guillaumet, “Functionalization of Imidazo[1,2-a]Pyridines by Means of Metal-Catalyzed Cross-Coupling Reactions,” European Journal of Organic Chemistry 2014, no. 24 (2014): 5119–38.
  • C. Burkholder, W. Dolbier, M. Medebielle, and S. Ait-Mohand, “Synthesis and Electron-Transfer Reactions of Some 3-Difluoroacetylated Imidazo[1,2- a] Pyridine Derivatives,” Tetrahedron Letters 42, no. 17 (2001): 3077–80.
  • A.K. Bagdi and A. Hajra, “Design, Synthesis, and Functionalization of Imidazoheterocycles,” Chemical Record (New York, N.Y.) 16, no. 4 (2016): 1868–85.
  • P. Kaswan, K. Pericherla, H.K. Saini, and H.S. Kumar, “One-Pot, Three Component Tandem Reaction of 2-Aminopyridines, Acetophenones and Aldehydes: synthesis of 3-Aroylimidazo[1,2- a] Pyridines,” RSC Advances 5, no. 5 (2015): 3670–7.
  • Y.-S. Tung, M.S. Coumar, Y.-S. Wu, H.-Y. Shiao, J.-Y. Chang, J.-P. Liou, P. Shukla, C.-W. Chang, C.-Y. Chang, C.-C. Kuo, et al, “Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics to Identify Orally Bioavailable Anticancer Agents,” Journal of Medicinal Chemistry 54, no. 8 (2011): 3076–80.
  • P.J. Sanfilippo, M. Urbanski, J.B. Press, and B. Dubinsky, “Synthesis of (Aryloxy)Alkylamines. 2. Novel Imidazo-Fused Heterocycles with Calcium Channel Blocking and Local Anesthetic Activity,” Journal of the American Chemical Society 138, no. 8 (2016): 2563–70.
  • M.-M. Xing, M. Xin, C. Shen, J.-R. Gao, J.-H. Jia, and Y-J. Li, “Iodine-Promoted Oxidative Coupling Reaction: A Simple and Efficient Process to Access Imidazo[1,2-a]Pyridines from 2-Aminopyridines and Chalcones,” Tetrahedron 72, no. 29 (2016): 4201–4.
  • X. Meng, J. Zhang, B. Chen, Z. Jing, and P. Zhao, “Copper Supported on H + -Modified Manganese Oxide Octahedral Molecular Sieves (Cu/H-OMS-2) as a Heterogeneous Biomimetic Catalyst for the Synthesis of Imidazo[1,2-a]-N-Heterocycles,” Catalysis Science & Technology 6, no. 3 (2016): 890–6.
  • P.V.S. Ramya, S. Angapelly, C.S. Digwal, U. Yadav, B.N. Babu, and A. Kamal, “An Efficient RuCl 3 ·H 2 O/I 2 Catalytic System: A Facile Access to 3-Aroylimidazo[1,2- a] Pyridines from 2-Aminopyridines and Chalcones,” Journal of Saudi Chemical Society 22, no. 1 (2018): 90–100.
  • F. Nemati, M. Kaveh, A. Elhampour, and M.S. Mirhosseyni, “Cu2O/Nano-CuFe2O4 as a Magnetically Recoverable Catalyst for Ligand-Free Synthesis of Imidazo[1,2-a] Pyridines and 3-Aroylimidazo[1,2-a] Pyridines,” National Academy Science Letters 42, no. 6 (2019): 479–84.
  • O.T.K. Nguyen, P.T. Ha, H.V. Dang, Y.H. Vo, T.T. Nguyen, N.T.H. Le, and N.T.S. Phan, “Superparamagnetic Nanoparticle-Catalyzed Coupling of 2-Amino Pyridines/Pyrimidines with Trans -Chalcones,” RSC Advances 9, no. 10 (2019): 5501–11.
  • N.H. Jadhav, S.S. Sakate, D.R. Shinde, M.G. Chaskar, and R.A. Pawar, “A Transition Metal-Free Cascade Reaction Using Heterogeneous Tin(IV)Oxide Catalyzed and Iodine Promoted Synthesis of 3-Aroylimidazo[1,2-a]Pyridines,” Tetrahedron Letters 61, no. 34 (2020): 152250.
  • K.R. Reddy, A.P. Gupta, and P. Das, “Metal-Free Aminooxygenation of Alkynes: Efficient Synthesis of 3-Aroylimidazo[1,2- a] - N -Heterocycles,” Asian Journal of Organic Chemistry 5, no. 7 (2016): 900–906.
  • Z. Chen, B. Liu, P. Liang, Z. Yang, and M. Ye, “Iron(III)-Catalyzed Synthesis of 3-Aroylimidazo[1,2-a]Pyridines from 2-Aminopyridines and Ynals,” Tetrahedron Letters 59, no. 7 (2018): 667–670.
  • L. Wei, F. Yao, F. Yi, and M. Cai, “Heterogeneous Gold(I)-Catalysed Annulation between 2-Aminopyridines and Propiolaldehydes Leading to 3-Acylimidazo[1,2-A]Pyridines,” Journal of Chemical Research 42, no. 7 (2018): 341–346.
  • C. Huo, J. Tang, H. Xie, Y. Wang, and J. Dong, “CBr4 Mediated Oxidative C–N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]Pyridines and Imidazo[1,2-α]Pyrimidines,” Organic Letters 18, no. 5 (2016): 1016–9.
  • B. Frett, N. McConnell, A. Kharbanda, G. Naresh, B. Rounseville, C. Warner, J. Chang, N. Debolske, and H.-Y. Li, “Selective, C-3 Friedel-Crafts Acylation to Generate Functionally Diverse, Acetylated Imidazo[1,2-a]Pyridine Derivatives,” Tetrahedron 74, no. 35 (2018): 4592–4600.
  • Y. Zhang, R. Chen, Z. Wang, L. Wang, and Y. Ma, “I2-Catalyzed Three-Component Consecutive Reaction for the Synthesis of 3-Aroylimidazo[1,2-a]-N-Heterocycles,” The Journal of Organic Chemistry 86V, no. 9 (2021): 6239–6246.

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