A Resilient and Reusable Ion-Tagged Cu(II) Catalyst for the Microwave-Assisted Synthesis of 2-(N-Arylamino)benzothiazoles

Md Gulzar Ahmad; M M Balamurali; Kaushik Chanda

doi:10.1055/a-2463-4827

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DOI: 10.1055/a-2463-4827

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Emerging Trends in Organic Chemistry: A Focus on India

A Resilient and Reusable Ion-Tagged Cu(II) Catalyst for the Microwave-Assisted Synthesis of 2-(N-Arylamino)benzothiazoles

Md Gulzar Ahmad

^aDepartment of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, 632014, India

,

M M Balamurali∗

^bChemistry Division, School of Advanced Sciences, Vellore Institute of Technology, Chennai Campus, Chennai, 600127, India

,

Kaushik Chanda ∗

^cDepartment of Chemistry, Rabindranath Tagore University, Hojai, 782435, India

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Abstract

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Abstract

A simple, quick, and cost-effective protocol is presented herein for the sustainable synthesis of 2-(N-arylamino)benzothiazoles from 2-haloanilines and arylisothiocyanates by using an ionic liquid supported heterogeneous Cu(II) catalyst derived from N-methylimidazole. Compared to the use of homogeneous catalysts and additives, which require long reaction times and high reaction temperatures, this methodology has a broad substrate scope and proceeds in short reaction times to afford compounds in excellent yields under microwave irradiation. In addition, the catalyst can be extracted easily and is recyclable up to five times with no significant loss in catalytic activity.

Key words

2-aminobenzothiazoles - ionic liquids - microwave irradiation - Cu(II) catalysts - sustainable synthesis

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References

References and Notes
1 Sweeney JB, Rattray M, Pugh V, Powell LA. ACS Med. Chem. Lett. 2018; 9: 552
2 Huang G, Cierpicki T, Grembecka J. Bioorg. Chem. 2023; 135: 106477
3 Salih OM, Al-Sha’er MA, Basheer HA. ACS Omega 2024; 9: 13928
4 Dadmal TL, Katre SD, Mandewale MC, Kumbhare RM. New J. Chem. 2018; 42: 776
5 Ismail TI, El-Khazragy N, Azzam RA. RSC Adv. 2024; 14: 16332
6 Javahershenas R, Han J, Kazemi M, Jervis PJ. ChemistryOpen 2024; e202400185
7 Elsadek MF, Ahmed BM, Farahat MF. Molecules 2021; 26: 1449
8 Awaad SS, Sarhan MO, Mahmoud WR, Nasr T, George RF, Georgey HH. J. Mol. Struct. 2023; 1291: 136042
9 Gu Y, Li Y.-D, Ge Y, Huang J.-L, Xu H.-J, Hu Y. Asian J. Org. Chem. 2024; 13: e202400076
10 Xu Y, Li B, Zhang X, Fan X. J. Org. Chem. 2017; 82: 9637
11 Zhilitskaya LV, Yarosh N. О. Chem. Heterocycl. Compd. 2021; 57: 369
12 Dias RF. C, Ribeiro BM. R. M, Cassani NM, Farago DN, Antoniucci GA, de Oliveira Rocha RE, de Oliveira Souza F, Pilau EJ, Jardim AC. G, Ferreira RS, de Oliveira Rezende Júnior C. Bioorg. Med. Chem. 2023; 95: 117488
13 Catalano A, Carocci A, Defrenza I, Muraglia M, Carrieri A, Van Bambeke F, Rosato A, Corbo F, Franchini C. Eur. J. Med. Chem. 2013; 64: 357
14 Philip RM, Saranya PV, Anilkumar G. ChemistrySelect 2024; 9: e202400001
15 Kant K, Patel CK, Banerjee S, Naik P, Padhi A, Sharma V, Singh V, Almeer R, Keremane KS, Atta AK, Malakar CC. Asian J. Org. Chem. 2024; 13: e202400223
16 Alizadeh SR, Hashemi SM. Med. Chem. Res. 2021; 30: 771
17 Benedí C, Bravo F, Uriz P, Fernández E, Claver C, Castillón S. Tetrahedron Lett. 2003; 44: 6073
18 Joyce LL, Evindar G, Batey RA. Chem. Commun. 2004; 446
19 Wang J, Peng F, Jiang J, Lu Z, Wang L, Bai J, Pan Y. Tetrahedron Lett. 2008; 49: 467
20 Chen L, Huang B, Nie Q, Cai M. Appl. Organomet. Chem. 2016; 30: 446
21 Parmar D, Sharma T, Sharma AK, Sharma U. Chem. Commun. 2023; 59: 9646
22 Qiu J.-W, Zhang X.-G, Tang R.-Y, Zhong P, Li J.-H. Adv. Synth. Catal. 2009; 351: 2319
23 Yang J, Li P, Wang L. Tetrahedron 2011; 67: 5543
24 Mishra N, Singh AS, Agrahari AK, Singh SK, Singh M, Tiwari VK. ACS Comb. Sci. 2019; 21: 389
25 Ding Q, Cao B, Liu X, Zong Z, Peng YY. Green Chem. 2010; 12: 1607
26 Zhao N, Liu L, Wang F, Li J, Zhang W. Adv. Synth. Catal. 2014; 356: 2575
27 Guo Y.-J, Tang R.-Y, Zhong P, Li J.-H. Tetrahedron Lett. 2010; 51: 649
28 Ding Q, He X, Wu J. J. Comb. Chem. 2009; 11: 587
29 Ahmad MG, Chanda K. Coord. Chem. Rev. 2022; 472: 214769
30 Urbán B, Szabó P, Srankó D, Sáfrán G, Kollár L, Skoda-Földes R. Mol. Catal. 2018; 445: 195
31 Deepa M, Selvarasu U, Kalaivani K, Parasuraman K. J. Organomet. Chem. 2021; 954–955: 122073
32 Fujie K, Kitagawa H. Coord. Chem. Rev. 2016; 307: 382
33 Nishanth Rao R, Jena S, Mukherjee M, Maiti B, Chanda K. Environ. Chem. Lett. 2021; 19: 3315
34 Martina K, Cravotto G, Varma RS. J. Org. Chem. 2021; 86: 13857
35 Ahmad MG, Balamurali MM, Chanda K. Tetrahedron Lett. 2024; 146: 155182
36 Dasmahapatra U, Chanda K, Maiti B. J. Heterocycl. Chem. 2024; 61: 761
37 Dasmahapatra U, Maiti B, Chanda K. Org. Biomol. Chem. 2024; 22: 8459
38 Rao RN, Das S, Jacob K, Alam MM, Balamurali MM, Chanda K. Org. Biomol. Chem. 2024; 22: 3249
39 Jena S, Gonzalez G, Vítek D, Kvasnicová M, Štěpánková S, Strnad M, Voller J, Chanda K. Eur. J. Med. Chem. 2024; 276: 116592
40 Synthesis of 2-(N-Arylamino)benzothiazoles 4; General Procedure: All reactions were carried out with a professional microwave oven equipped with a condenser and a glass vial extension (Model No. Cata R; Catalyst Systems, Pune) fitted with an external probe temperature control system to regulate the temperature. 2-Halobenzeneamine 2 (1 mmol) and arylisothiocyanate 3 (1 mmol) were dissolved in DMSO, then catalyst 1 (5 mol%) and K₂CO₃ were added. The mixture was then subjected to microwave irradiation for 12–15 min. The crude products were purified by washing with hexane/ethyl acetate (8:2) and were characterized by ¹H, ¹³C NMR, and HRMS analyses. This methodology has broad substrate scope and gave up to 95% isolated yield.

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