Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Letter Article

Sonication Assisted One-Pot Synthesis of Substituted Imidazopyridine from Styrene in Water

Author(s): Sanjay Subhas Gaikwad, Nitin Madhu Thorat and Limbraj Rajaram Patil*

Volume 18, Issue 4, 2021

Published on: 05 November, 2020

Page: [366 - 370] Pages: 5

DOI: 10.2174/1570179417999201105160447

Price: $65

Abstract

The present protocol is a simple and eco-friendly approach for the one-pot procedure for the synthesis of substituted imidazopyridines ranging from important feedstock’s like styrene promoted by NBS. Through sonicator and microwave commercially available styrene with NBS in water followed by reaction with 2- aminopyridines afforded important heterocyclic scaffolds in an one-pot procedure.

Keywords: One-pot synthesis, imidazopyridines, microwave condition, sonication condition, green synthesis, NBS.

Graphical Abstract

[1]
Bowles, K.D.; Quincy, D.; Mallet, B.; McKenna, J.I.; Natale, N.R. Heterocycles and reactive intermediates in the undergraduate organic lab. J. Chem. Educ., 1985, 62(12), 1118.
[http://dx.doi.org/10.1021/ed062p1118]
[2]
Ikemoto, T.; Wakimasu, M. Reactions with n-chlorosuccinimide of various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position. Heterocycles, 2001, 55, 99.
[http://dx.doi.org/10.3987/COM-00-9063]
[3]
Feng, S.; Hong, D.; Wang, B.; Zheng, X.; Miao, K.; Wang, L.; Yun, H.; Gao, L.; Zhao, S.; Shen, H.C. Discovery of imidazopyridine derivatives as highly potent respiratory syncytial virus fusion inhibitors. ACS Med. Chem. Lett., 2015, 6(3), 359-362.
[http://dx.doi.org/10.1021/acsmedchemlett.5b00008] [PMID: 25941547]
[4]
Saint-Ruf, G.; Loukakou, B.; N’Zouzi, C. Discovery of imidazopyridine derivatives as highly potent respiratory syncytial virus fusion inhibitors. J. Heterocycl. Chem., 1981, 18, 1565.
[http://dx.doi.org/10.1002/jhet.5570180816]
[5]
Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.; Biancotti, A.; Gamba, A.; Murmann, W. DERIVATIVES OF IMIDAZOLE. I. Synthesis and reactions of imidazo(1,2-a)pyridines with analgesic, anti-inflammatory, antipyretic, and anticonvulsant activity. J. Med. Chem., 1965, 8, 305-312.
[http://dx.doi.org/10.1021/jm00327a007] [PMID: 14329509]
[6]
Chen, G.; Liu, Z.; Zhang, Y.; Shan, X.; Jiang, L.; Zhao, Y.; He, W.; Feng, Z.; Yang, S.; Liang, G. Synthesis and anti-inflammatory evaluation of novel benzimidazole and imidazopyridine derivatives. ACS Med. Chem. Lett., 2012, 4(1), 69-74.
[http://dx.doi.org/10.1021/ml300282t] [PMID: 24900565]
[7]
Lacerda, R.B.; de Lima, C.K.F.; da Silva, L.L.; Romeiro, N.C.; Miranda, A.L.P.; Barreiro, E.J.; Fraga, C.A.M. Discovery of novel analgesic and anti-inflammatory 3-arylamine-imidazo[1,2-a]pyridine symbiotic prototypes. Bioorg. Med. Chem., 2009, 17(1), 74-84.
[http://dx.doi.org/10.1016/j.bmc.2008.11.018] [PMID: 19059783]
[8]
Tully, W.R.; Gardner, C.R.; Gillespie, R.J.; Westwood, R. 2-(oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors. J. Med. Chem., 1991, 34(7), 2060-2067.
[http://dx.doi.org/10.1021/jm00111a021] [PMID: 1648620]
[9]
Langer, S.Z.; Arbilla, S.; Benavides, J.; Scatton, B. Zolpidem and alpidem: two imidazopyridines with selectivity for omega 1- and omega 3-receptor subtypes. Adv. Biochem. Psychopharmacol., 1990, 46, 61-72.
[PMID: 1981304]
[10]
Sanfilippo, P.J.; Urbanski, M.; Press, J.B.; Dubinsky, B.; Moore, J.B. Jr Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity. J. Med. Chem., 1988, 31(11), 2221-2227.
[http://dx.doi.org/10.1021/jm00119a026] [PMID: 3184128]
[11]
Gueiffier, A.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.C.; Kerbal, A.; Essassi, E.M.; Debouzy, J.C.; Witvrouw, M.; Blache, Y.; Balzarini, J.; De Clercq, E.; Chapat, J.P. Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents. J. Med. Chem., 1996, 39(14), 2856-2859.
[http://dx.doi.org/10.1021/jm9507901] [PMID: 8709116]
[12]
Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.C.; Witvrouw, M.; Balzarini, J.; De Clercq, E.; Chapat, J.P. Synthesis of imidazo[1,2-a]pyridines as antiviral agents. J. Med. Chem., 1998, 41(25), 5108-5112.
[http://dx.doi.org/10.1021/jm981051y] [PMID: 9836626]
[13]
Banie, H.; Sinha, A.; Thomas, R.J.; Sircar, J.C.; Richards, M.L. 2-phenylimidazopyridines, a new series of golgi compounds with potent antiviral activity. J. Med. Chem., 2007, 50(24), 5984-5993.
[http://dx.doi.org/10.1021/jm0704907] [PMID: 17973358]
[14]
Rival, Y.; Grassy, G.; Michel, G. Synthesis and antibacterial activity of some imidazo[1,2-a]pyrimidine derivatives. Chem. Pharm. Bull. (Tokyo), 1992, 40(5), 1170-1176.
[http://dx.doi.org/10.1248/cpb.40.1170] [PMID: 1394630]
[15]
Rival, Y.; Grassy, G.; Taudou, A.; Ecalle, R. Antifungal activity in vitro of some imidazo[1,2-a]pyrimidine derivatives Activité antifongique in vitro de quelques dérivés de l’imidazo[1,2-a]pyrimidine. Eur. J. Med. Chem., 1991, 26, 13.
[http://dx.doi.org/10.1016/0223-5234(91)90208-5]
[16]
Swainston Harrison, T.; Keating, G.M. Zolpidem: A review of its use in the management of insomnia. CNS Drugs, 2005, 19(1), 65-89.
[http://dx.doi.org/10.2165/00023210-200519010-00008] [PMID: 15651908]
[17]
Bochis, R.J.; Olen, L.E.; Fisher, M.H.; Reamer, R.A.; Wilks, G.; Taylor, J.E.; Olson, G. Isomeric phenylthioimidazo[1,2-alpha]pyridines as anthelmintics. J. Med. Chem., 1981, 24(12), 1483-1487.
[http://dx.doi.org/10.1021/jm00144a022] [PMID: 7310824]
[18]
Spitzer, W.A.; Victor, F.; Pollock, G.D.; Hayes, J.S. Imidazo[1,2-a]pyrimidines and imidazo[1,2-a]pyrazines: The role of nitrogen position in inotropic activity. J. Med. Chem., 1988, 31(8), 1590-1595.
[http://dx.doi.org/10.1021/jm00403a018] [PMID: 3397997]
[19]
Tomoda, H.; Hirano, T.; Saito, S.; Mutai, T.; Araki, K. Substituent effects on fluorescent properties of imidazo[1,2-a]pyridine-based compounds. Bull. Chem. Soc. Jpn., 1999, 72, 1327.
[http://dx.doi.org/10.1246/bcsj.72.1327]
[20]
Gudmundsson, K.S.; Johns, B.A. Synthesis of novel imidazo[1,2-a]pyridines with potent activity against herpesviruses. Org. Lett., 2003, 5(8), 1369-1372.
[http://dx.doi.org/10.1021/ol0343616] [PMID: 12688761]
[21]
Ghosh, K.; Nishii, Y.; Miura, M. Oxidative C-H/C-H annulation of imidazopyridines and indazoles through rhodium-catalyzed vinylene transfer. Org. Lett., 2020, 22(9), 3547-3550.
[http://dx.doi.org/10.1021/acs.orglett.0c00975] [PMID: 32282221]
[22]
Yan, R-L.; Yan, H.; Ma, C.; Ren, Z-Y.; Gao, X-A.; Huang, G-S.; Liang, Y-M. Cu(I)-catalyzed synthesis of imidazo[1,2-a]pyridines from aminopyridines and nitroolefins using air as the oxidant. J. Org. Chem., 2012, 77(4), 2024-2028.
[http://dx.doi.org/10.1021/jo202447p] [PMID: 22239920]
[23]
Katritzky, A.R.; Xu, Y.J.; He, H.Y.; Mehta, S. Syntheses of 1,4-benzothiazepines and 1,4-benzoxazepines via cyclizations of 1-[2-arylthio(oxy)ethyl]-5-benzotriazolyl-2-pyrrolidinones and 3-benzotriazolyl-2-[2-arylthio(oxy)ethyl]-1-isoindolinones. J. Org. Chem., 2001, 66(16), 5590-5594.
[http://dx.doi.org/10.1021/jo010179b] [PMID: 11485488]
[24]
Liu, P.; Fang, L-s.; Lei, X.; Lin, G-q. Synthesis of imidazo[1,2a]pyridines via three-component reaction of 2-aminopyridines, aldehydes and alkynes. Tetrahedron Lett., 2010, 51(35), 4605-4608.
[http://dx.doi.org/10.1016/j.tetlet.2010.05.139]
[25]
Chernyak, N.; Gevorgyan, V. General and efficient copper-catalyzed three-component coupling reaction towards imidazoheterocycles: One-pot synthesis of alpidem and zolpidem. Angew. Chem. Int. Ed. Engl., 2010, 49(15), 2743-2746.
[http://dx.doi.org/10.1002/anie.200907291] [PMID: 20213787]
[26]
Palani, T.; Park, K.; Kumar, M.R.; Jung, H.M.; Lee, S. Copper‐Catalyzed decarboxylative three‐component reactions for the synthesis of imidazo[1,2‐a]pyridines. Eur. J. Org. Chem., 2012, (26), 5038-5047.
[http://dx.doi.org/10.1002/ejoc.201200679]
[27]
Mandair, G.S.; Light, M.; Russell, A.; Hursthouse, M.; Bradley, M. Re-evaluation of the outcome of a multiple component reaction-2- and 3-amino-imidazo[1,2-a]pyrimidines? Tetrahedron Lett., 2002, 43, 4267.
[http://dx.doi.org/10.1016/S0040-4039(02)00709-8]
[28]
Liu, P.; Deng, C-L.; Lei, X.; Lin, G-q. Tandem amination/cycloisomerization of aryl propargylic alcohols with 2‐aminopyridines as an expedient route to imidazo[1,2‐a]pyridines. Eur. J. Org. Chem., 2011, 2011(36), 7308-7316.
[http://dx.doi.org/10.1002/ejoc.201101053]
[29]
Bristow, N.W.; Charlton, P.T.; Peak, D.A.; Short, W.F. Meso-ionic compounds derived from pyridino(1′: 2′-1: 2)glyoxaline. J. Chem. Soc., 1954, 616.
[http://dx.doi.org/10.1039/JR9540000616]
[30]
Katritzky, A.R.; Xu, Y-J.; Tu, H. Regiospecific synthesis of 3-substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine. J. Org. Chem., 2003, 68(12), 4935-4937.
[http://dx.doi.org/10.1021/jo026797p] [PMID: 12790603]
[31]
Groziak, M.P.; Wilson, S.R.; Clauson, G.L.; Leonard, N.J. Fluorescent heterocyclic systems: syntheses, structures, and physicochemical properties of dipyrido-substituted 1,3,4,6-tetraazapentalenes. J. Am. Chem. Soc., 1986, 108, 8002.
[http://dx.doi.org/10.1021/ja00285a020]
[32]
Zhang, Y.; Chen, Z.; Wu, W.; Zhang, Y.; Su, W. CuI-catalyzed aerobic oxidative α-aminaton cyclization of ketones to access aryl or alkenyl-substituted imidazoheterocycles. J. Org. Chem., 2013, 78(24), 12494-12504.
[http://dx.doi.org/10.1021/jo402134x] [PMID: 24256374]
[33]
Bagdi, A.K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. 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. Adv. Synth. Catal., 2013, 355(9), 1741-1747.
[http://dx.doi.org/10.1002/adsc.201300298]
[34]
Byth, K.F.; Culshaw, J.D.; Green, S.; Oakes, S.E.; Thomas, A.P. Imidazo[1,2-a]pyridines. Part 2: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(9), 2245-2248.
[http://dx.doi.org/10.1016/j.bmcl.2004.02.015] [PMID: 15081017]
[35]
Löber, S.; Hübner, H.; Gmeiner, P. Azaindole derivatives with high affinity for the dopamine D4 receptor: Synthesis, ligand binding studies and comparison of molecular electrostatic potential maps. Bioorg. Med. Chem. Lett., 1999, 9(1), 97-102.
[http://dx.doi.org/10.1016/S0960-894X(98)00692-1] [PMID: 9990464]
[36]
Katritzky, A.R.; Lan, X.; Yang, J.Z.; Denisko, O.V. Properties and Synthetic Utility of N-Substituted Benzotriazoles. Chem. Rev., 1998, 98(2), 409-548.
[http://dx.doi.org/10.1021/cr941170v] [PMID: 11848906]
[37]
Knott, E.B. Heterocyclyl-rhodanines and -2-thiohydantoins. J. Chem. Soc., 1956, 1644.
[http://dx.doi.org/10.1039/jr9560001644]
[38]
Pericherla, K. Recent developments in the synthesis of imidazo[1,2-a]pyridines. Synthesis, 2015, 47, 887-912.
[http://dx.doi.org/10.1055/s-0034-1380182]
[39]
Groebke, K.; Weber, L.; Mehlin, F. Synthesis of imidazo[1,2-a] annulated pyridines, pyrazines and pyrimidines by a novel three-component condensation. Synlett, 1998, 661.
[http://dx.doi.org/10.1055/s-1998-1721]
[40]
Katritzky, A.R.; Fan, W.Q.; Fu, C. The chemistry of benzotriazole. A novel method for the synthesis of symmetrical vicinal tertiary and secondary diamines. J. Org. Chem., 1990, 55, 3209.
[http://dx.doi.org/10.1021/jo00297a042]
[41]
Hand, E.S.; Paudler, W.W. Teleamination of the imidazo[1,2-a]pyridine system. J. Org. Chem., 1978, 43, 2900.
[http://dx.doi.org/10.1021/jo00408a033]
[42]
Rydzkowski, R.; Blondeau, D.; Sliwa, H. Synthesis of new heterocyclic phenols: 8-hydroxy-imidazo [1,2-a] pyridine. Tetrahedron Lett., 1985, 26, 2571.
[http://dx.doi.org/10.1016/S0040-4039(00)98839-7]
[43]
Zhang, X.; Li, J.; Tian, H.; Shi, Y. Catalytic asymmetric bromination of unfunctionalized olefins with h2o as a nucleophile. Chemistry, 2015, 21(33), 11658-11663.
[http://dx.doi.org/10.1002/chem.201502133] [PMID: 26137926]
[44]
Chezal, J.M.; Moreau, E.; Delmas, G.; Gueiffier, A.; Blache, Y.; Grassy, G.; Lartigue, C.; Chavignon, O.; Teulade, J.C. Heterocyclization of functionalized vinylic derivatives of imidazo. J. Org. Chem., 2001, 66(20), 6576-6584.
[http://dx.doi.org/10.1021/jo015582x] [PMID: 11578207]
[45]
Simon, M-O.; Li, C-J. Green chemistry oriented organic synthesis in water. Chem. Soc. Rev., 2012, 41(4), 1415-1427.
[http://dx.doi.org/10.1039/C1CS15222J] [PMID: 22048162]
[46]
Alix, A.; Lalli, C.; Retailleau, P.; Masson, G. Highly enantioselective electrophilic α-bromination of enecarbamates: Chiral phosphoric acid and calcium phosphate salt catalysts. J. Am. Chem. Soc., 2012, 134(25), 10389-10392.
[http://dx.doi.org/10.1021/ja304095z] [PMID: 22686436]
[47]
Rajbongshi, K.K.; Hazarika, D.; Phukan, P. Tetrahedron Lett., 2015, 56(2), 356-358.
[http://dx.doi.org/10.1016/j.tetlet.2014.11.096]
[48]
Song, L.; Luo, S.; Cheng, J-P. Catalytic intermolecular haloamidation of simple alkenes with N-halophthalimide as both nitrogen and halogen source. Org. Lett., 2013, 15(22), 5702-5705.
[http://dx.doi.org/10.1021/ol402726d] [PMID: 24156477]
[49]
Zhou, L.; Chen, J.; Zhou, J.; Yeung, Y-Y. N-Bromosuccinimide promoted one-pot synthesis of guanidine: scope and mechanism. Org. Lett., 2011, 13(21), 5804-5807.
[http://dx.doi.org/10.1021/ol202402y] [PMID: 21988188]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy