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Synlett
DOI: 10.1055/a-2463-4827
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
The authors wish to thank the management of the Vellore Institute of Technology (VIT) for providing seed money as a research grant.
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2463-4827.
- Supporting Information
Publication History
Received: 25 September 2024
Accepted after revision: 07 November 2024
Accepted Manuscript online:
07 November 2024
Article published online:
02 December 2024
© 2024. Thieme. All rights reserved
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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.