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Synlett 2016; 27(09): 1387-1390
DOI: 10.1055/s-0035-1561575
DOI: 10.1055/s-0035-1561575
letter
Catalyst-Free Synthesis of 2-Arylbenzothiazoles in an Air/DMSO Oxidant System
Further Information
Publication History
Received: 04 November 2015
Accepted after revision: 23 January 2016
Publication Date:
25 February 2016 (online)
Abstract
A straightforward strategy for the synthesis of 2-arylbenzothiazoles from 2-aminothiophenol and aryl aldehydes in air/DMSO oxidant system has been developed. This reaction is operationally simple, proceeds without catalysts, tolerates a wide range of functionalities, and provides desired products in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561575.
- Supporting Information
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- 14 Typical Procedure 2-Aminothiophenol (1a, 0.5 mmol, 1.0 equiv) and benzaldehyde (2a, 0.6 mmol, 1.2 equiv) were dissolved in DMSO (3 mL). Then, the reaction mixture was stirred at 60 °C for 6 h. After the reaction, H2O was added to the mixture. The mixture was extracted with EtOAc (3 × 20 mL). The combined organic layers were then washed with sat. aq NaCl (30 mL). The solution was dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified with silica gel chromatography (EtOAc–PE, 1:30) to give pure compound 3a in 96% yield. Selected Spectral Data for 2-Phenylbenzothiazole (3a) 1H NMR (300 MHz, CDCl3): δ = 8.07–8.12 (m, 3 H), 7.91 (d, J = 9.0 Hz, 1 H), 7.48–7.51 (m, 4 H), 7.39 (t, J = 9.0 Hz, 1 H).