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

Synlett, Table of Contents

Synlett 2025; 36(15): 2345-2349
DOI: 10.1055/a-2463-4827

letter

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

Authors

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

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

Full Text

References

References and Notes
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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.

Supplementary Material

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