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Synthesis 2025; 57(01): 196-208
DOI: 10.1055/a-2369-3893
DOI: 10.1055/a-2369-3893
paper
Special Topic Dedicated to Prof. H. Ila
Transition-Metal-Catalyzed Rapid Synthesis of Imidazo[2,1-b]thiazoles: Access to Aza-Fused Heterocycles via Aerobic Oxidative Coupling of 2-Aminothiazoles and Acetophenones
J.D. thanks the Wellcome Trust DBT India Alliance (Grant Number IA/S/18/2/503986) and Department of Science and Technology, Ministry of Science and Technology, India (CRG) for funding. S.J.B. thanks the Council of Scientific and Industrial Research, India for a senior research fellowship.
Dedicated to Professor Hiriyakkanavar Ila on the occasion of her 80th birthday.
Abstract
We report an efficient synthesis of 6-substituted imidazo[2,1-b]thiazoles from 2-aminothiazoles and acetophenones through intramolecular cyclization of in situ generated thiazolium ylides. This one-pot cascade process efficiently forms two C–N bonds and is facilitated by both Cu(OTf)2/KI and FeCl3/ZnI2 systems. The method utilizes commercially available starting materials and features mild reaction conditions, tolerance to different functional groups, and ease of operation. The synthetic applicability has further been demonstrated through post-modification of imidazo[2,1-b]thiazole analogues.
Key words
2-aminothiazoles - acetophenones - 6-phenylimidazo[2,1-b]thiazoles - thiazolium ylide intermediate - transition-metal-catalyzed C–H bond activationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2369-3893.
- Supporting Information
Publication History
Received: 31 May 2024
Accepted after revision: 18 July 2024
Accepted Manuscript online:
18 July 2024
Article published online:
13 August 2024
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References
- 1a Budriesi R, Ioan P, Leoni A, Pedemonte N, Locatelli A, Micucci M, Chiarini A, Galietta LJ. V. J. Med. Chem. 2011; 54: 3885
- 1b Güzeldemirci NU, Küçükbasmacı Ö. Eur. J. Med. Chem. 2010; 45: 63
- 1c Metaye T, Millet C, Kraimps JL, Saunier B, Barbier J, Begon F. Biochem. Pharmacol. 1992; 43: 1507
- 2a 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
- 2b Gürsoy E, Güzeldemirci NU. Eur. J. Med. Chem. 2007; 42: 320
- 2c Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Calonghi N, Cappadone C, Farruggia G, Zini M, Stefanelli C, Masotti L, Radin NS, Shoemaker RH, Andreani A. J. Med. Chem. 2008; 51: 809
- 2d Park J.-H, El-Gamal MI, Lee YS, Oh C.-H. Eur. J. Med. Chem. 2011; 46: 5769
- 2e Sbenati RM, Semreen MH, Semreen AM, Shehata MK, Alsaghir FM, El-Gamal MI. Bioorg. Med. Chem. 2021; 29: 115897
- 3 Raeymaekers AH. M, Allewijn FT. N, Vandenberk J, Demoen PJ. A, Van Offenwert TT. T, Janssen PA. J. J. Med. Chem. 1966; 9: 545
- 4 Scribner A, Meitz S, Fisher M, Wyvratt M, Leavitt P, Liberator P, Gurnett A, Brown C, Mathew J, Thompson D, Schmatz D, Biftu T. Bioorg. Med. Chem. Lett. 2008; 18: 5263
- 5 Yousefi BH, Manook A, Drzezga A, v. Reutern B, Schwaiger M, Wester H.-J, Henriksen G. J. Med. Chem. 2011; 54: 949
- 6 Lipson VV, Yaremenko FG, Vakula VM, Kovalenko SV, Kyrychenko AV, Desenko SM, Musatov VI, Borysko PO, Zozulya SO. Funct. Matter. 2023; 30: 486
- 7a Herath A, Dahl R, Cosford ND. P. Org. Lett. 2010; 12: 412
- 7b Denora N, Laquintana V, Pisu MG, Dore R, Murru L, Latrofa L, Trapani G, Sanna E. J. Med. Chem. 2008; 51: 6876
- 7c Paudler WW, Kuder JE. J. Org. Chem. 1966; 31: 809
- 7d Brouwer C, Sinclair K, Cuevas J, Pike VW, Cai L. Synthesis 2006; 133
- 7e Chunavala KC, Joshi G, Suresh E, Adimurthy S. Synthesis 2011; 635
- 7f Mohamadi A, Sheikhi E, Ansari S, Bijanzadeh HR, Adib M. Synlett 2010; 1606
- 8a Xie Y.-Y, Zheng Q.-G, Chen Q.-G. Synthesis 2002; 1505
- 8b Yadav JS, Subba Reddy BV, Gopal Rao Y, Srinivas M, Narsaiah AV. Tetrahedron 2007; 48: 7717
- 8c Sumran G, Aggarwal R. Synth. Commun. 2006; 36: 875
- 8d Mukku N, Maiti B. RSC Adv. 2020; 10: 770
- 8e Bangade VM, Reddy BC, Thakur PB, Babu BM, Meshram HM. Tetrahedron Lett. 2013; 54: 4767
- 9 Omar MA, Frey W, Conrad J, Beifuss U. J. Org. Chem. 2014; 79: 10367
- 10 Rassokhina IV, Tikhonova TA, Kobylskoy SG, Babkin IY, Shirinian VZ, Gevorgyan V, Zavarzin IV, Volkova YA. J. Org. Chem. 2017; 82: 9682
- 11 Chen Z, Jin W, Xia Y, Zhang Y, Xie M, Ma S, Liu C. Org. Lett. 2020; 22: 8261
- 12 Chen Z, Xue F, Zhang Y, Jin W, Wang B, Xia Y, Xie M, Abdukader A, Liu C. Org. Lett. 2022; 24: 3149
- 13 Mishra S, Monir K, Mitra S, Hajra A. Org. Lett. 2014; 16: 6084
- 14a Louillat M.-L, Patureau FW. Chem. Soc. Rev. 2014; 43: 901
- 14b Shi ZZ, Zhang C, Tang CH, Jiao N. Chem. Soc. Rev. 2012; 41: 3381
- 14c Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
- 14d Punniyamurthy T, Velusamy S, Iqbal J. Chem. Rev. 2005; 105: 2329
- 14e Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
- 14f Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
- 15a Midya GC, Paladhi S, Dhara K, Dash J. Chem. Commun. 2011; 47: 6698
- 15b Maiti S, Burgula L, Chakraborti G, Dash J. Eur. J. Org. Chem. 2017; 332
- 15c Maiti S, Mandal T, Dash B, Dash J. J. Org. Chem. 2021; 86: 1396
- 16a Dhara K, Mandal T, Das J, Dash J. Angew. Chem. Int. Ed. 2015; 54: 15831 ; Angew. Chem. 2015, 127, 16057
- 16b Mandal T, Chakraborti G, Karmakar S, Dash J. Org. Lett. 2018; 20: 4759
- 16c Mandal T, Karmakar S, Kapat A, Dash J. ACS Omega 2021; 6: 27062
- 16d Ghosh T, Mandal I, Basak SJ, Dash J. J. Org. Chem. 2021; 86: 14695
- 16e Basak SJ, Dash J. J. Org. Chem. 2024; 89: 233
- 16f Basak SJ, Dash J. J. Org. Chem. 2024; 89: 3612
- 17 CCDC 2359527 (3af) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures