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Synlett 2024; 35(16): 1899-1905
DOI: 10.1055/s-0042-1751565
DOI: 10.1055/s-0042-1751565
letter
Ultrasound-Mediated Green Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles through C(sp3)–H Functionalization
Abstract
An ultrasound-assisted expedient protocol has been developed for the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles by the C–H functionalization of ketones using a KI/tert-butyl hydroperoxide catalytic system. The reaction takes place in water, a green solvent, and does not require a metal catalyst; it also gives good yields of the products. The method offers numerous noteworthy characteristics, including mild reaction conditions, the absence of a base, broad functional-group compatibility, and excellent reaction yields. Moreover, it avoids the use of costly and air-sensitive chemicals, and can be conducted under ambient reaction conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751565.
- Supporting Information
Publication History
Received: 05 February 2024
Accepted: 07 February 2024
Article published online:
26 February 2024
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References and Notes
- 1a Pericherla K, Kaswan P, Khedar P, Khungar B, Parang K, Kumar A. RSC Adv. 2013; 3: 18923
- 1b Chen K, Baran PS. Nature 2009; 459: 824
- 1c Dangel BD, Godula K, Youn SW, Sezen B, Sames D. J. Am. Chem. Soc. 2002; 124: 11856
- 2a Bhagat SB, Telvekar VN. Tetrahedron Lett. 2017; 58: 3662
- 2b Rupert KC, Henry JR, Dodd JH, Wadsworth SA, Cavender DE, Olini GC, Fahmy B, Siekierka JJ. Bioorg. Med. Chem. Lett. 2003; 13: 347
- 3a Almirante L, Polo L, Mugnaini A, Provinciali E, Rugarli P, Biancotti A, Gamba A, Murmann W. J. Med. Chem. 1965; 8: 305
- 3b Elhakmaoui A, Gueiffier A, Milhavet J.-C, Blache Y, Chapat J.-P, Chavignon O, Teulade J.-C, Snoeck R, Andrei G, De Clercq E. Bioorg. Med. Chem. Lett. 1994; 4: 1937
- 3c Starrett JE. Jr, Montzka TA, Crosswell AR, Cavanagh RL. J. Med. Chem. 1989; 32: 2204
- 3d Hamdouchi C, de Blas J, del Prado M, Gruber J, Heinz BA, Vance L. J. Med. Chem. 1999; 42: 50
- 3e Byth KF, Culshaw JD, Green S, Oakes SE, Thomas AP. Bioorg. Med. Chem. Lett. 2004; 14: 2245
- 3f Lacerda RB, de Lima CK. F, da Silva LL, Romeiro NC, Miranda AL. P, Barreiro EJ, Fraga CA. M. Bioorg. Med. Chem. Lett. 2009; 17: 74
- 3g Abe Y, Kayakiri H, Satoh S, Inoue T, Sawada Y, Imai K, Inamura N, Asano M, Hatori C, Katayama A, Oku T, Tanaka H. J. Med. Chem. 1998; 41: 564
- 3h Humphries AC, Gancia E, Gilligan MT, Goodacre S, Hallett D, Merchant KJ, Thomas SR. Bioorg. Med. Chem. Lett. 2006; 16: 1518
- 3i Boggs S, Elitzin VI, Gudmundsson K, Martin MT, Sharp MJ. Org. Process Res. Dev. 2009; 13: 781
- 3j Jain AN. J. Med. Chem. 2004; 47: 947
- 4a Güzeldemirci NU, Küçükbasmacı Ö. Eur. J. Med. Chem. 2010; 45: 63
- 4b Andreani A, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Lenaz G, Fato R, Bergamini C, Farruggia G. J. Med. Chem. 2005; 48: 3085
- 5a Meng X, Yu C, Chen G, Zhao P. Catal. Sci. Technol. 2015; 5: 372
- 5b Zhu D.-J, Chen J.-X, Liu M.-C, Ding J.-C, Wu H.-Y. J. Braz. Chem. Soc. 2009; 20: 482
- 5c Yan H, Yang S, Gao X, Zhou K, Ma C, Yan R, Huang G. Synlett 2012; 2961
- 5d Cao H, Zhan H, Lin Y, Lin X, Du Z, Jiang H. Org. Lett. 2012; 14: 1688
- 5e Rodríguez JC, Maldonado RA, Ramírez-García G, Díaz Cervantes E, de la Cruz FN. J. Heterocycl. Chem. 2020; 57: 2279
- 5f Stasyuk AJ, Banasiewicz M, Cyrański MK, Gryko DT. J. Org. Chem. 2012; 77: 5552
- 5g Wang H, Wang Y, Liang D, Liu L, Zhang J, Zhu Q. Angew. Chem. Int. Ed. 2011; 50: 5678
- 5h He C, Hao J, Xu H, Mo Y, Liu H, Han J, Lei A. Chem. Commun. 2012; 48: 11073
- 5i Ge W, Zhu X, Wei Y. Eur. J. Org. Chem. 2013; 2013: 6015
- 5j Santra S, Bagdi AK, Majee A, Hajra A. Adv. Synth. Catal. 2013; 355: 1065
- 5k Cai Q, Liu M.-C, Mao B.-M, Xie X, Jia F.-C, Zhu Y.-P, Wu A.-X. Chin. Chem. Lett. 2015; 26: 881
- 6a Palani T, Park K, Kumar MR, Jung HM, Lee S. Eur. J. Org. Chem. 2012; 2012: 5038
- 6b Masquelin T, Bui H, Brickley B, Stephenson G, Schwerkoske J, Hulme C. Tetrahedron Lett. 2006; 47: 2989
- 6c Khan AT, Basha RS, Lal M. Tetrahedron Lett. 2012; 53: 2211
- 6d Chernyak N, Gevorgyan V. Angew. Chem. Int. Ed. 2010; 49: 2743
- 6e Lyon MA, Kercher TS. Org. Lett. 2004; 6: 4989
- 6f Burchak ON, Mugherli L, Ostuni M, Lacapère JJ, Balakirev MY. J. Am. Chem. Soc. 2011; 133: 10058
- 7a Huang H.-M, Huang F, Li Y.-J, Jia J.-H, Ye Q, Han L, Gao J.-R. RSC Adv. 2014; 4: 27250
- 7b Zhang J, Jiang J, Li Y, Wan X. J. Org. Chem. 2013; 78: 11366
- 7c Li X, Xu X, Hu P, Xiao X, Zhou C. J. Org. Chem 2013; 78: 7343
- 7d Reddy KR, Venkateshwar M, Maheswari CU, Kumar PS. Tetrahedron Lett. 2010; 51: 2170
- 7e Li H.-L, Wang Y, Sun P.-P, Luo X, Shen Z, Deng W.-P. Chem. Eur. J. 2016; 22: 9348
- 7f Maheswari CU, Kumar GS, Venkateshwar M. RSC Adv. 2014; 4: 39897
- 8a Amrollahi MA, Kheilkordi Z. J. Iran. Chem. Soc. 2016; 13: 925
- 8b Chauhan S, Verma P, Mishra A, Srivastava V. Chem. Heterocycl. Compd. 2020; 56: 123
- 8c Kondabanthini S, Katari NK, Srimannarayana M, Gundla R, Kapavarapu R, Pal M. J. Mol. Struct. 2022; 1266: 133527
- 8d Addu N, Miriyala H, Kapavarapu R, Kolli SK, Pal M. J. Mol. Struct. 2023; 1283: 135313
- 9 Imidazo[1,2-a]pyridines 3aa–hc; General Procedure A flask was charged with the appropriate aryl methyl ketone 1 (1.0 mmol), 2-aminopyridine 2 (1.0 mmol), KI (0.5 equiv), TBHP (1.0 equiv), and H2O (3 mL) at r.t., and the mixture was exposed to ultrasound irradiation until the reaction was complete (TLC). The mixture was extracted with EtOAc, and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, EtOAc–hexane). 2-Phenylimidazo[1,2-a]pyridine (3aa)10a White solid; yield:188 mg (97%); mp 135–136 °C. 1H NMR (500 MHz, CDCl3): δ = 8.11 (dt, J = 6.7, 1.1 Hz, 1 H), 7.99–7.93 (m, 2 H), 7.86 (s, 1 H), 7.66–7.60 (m, 1 H), 7.47–7.41 (m, 2 H), 7.37–7.30 (m, 1 H), 7.19–7.13 (m, 1 H), 6.77 (td, J = 6.8, 1.0 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 145.97, 145.83, 133.90, 128.86, 128.11, 126.19, 125.71, 124.77, 117.73, 112.55, 108.24. 2-Phenylimidazo[2,1-b][1,3]benzothiazole (3ae)10b Yellow solid; yield: 235 mg (94%); mp 106–107 °C. 1H NMR (500 MHz, CDCl3): δ = 7.96 (s, 1 H), 7.88 (d, J = 8.2 Hz, 2 H), 7.69 (d, J = 8.5 Hz, 1 H), 7.60 (d, J = 8.0 Hz, 1 H), 7.46–7.40 (m, 3 H), 7.32 (dt, J = 15.0, 7.7 Hz, 2 H). 13C NMR (126 MHz, CDCl3): δ = 148.2, 147.8, 133.9, 132.3, 130.4, 128.8, 127.6, 126.3, 125.3, 124.9, 124.5, 112.7, 106.9.