Synthesis of Benzo[c]isothiazole 2-Oxides via Copper-Catalyzed Cycloamidation Reaction

Abstract

Herein, a modular and efficient approach towards benzo[c]isothiazole 2-oxides via a copper-catalyzed intramolecular C–N cross-coupling reaction was disclosed. Readily available starting materials, broad substrate scope, outstanding yields (up to 95%), and scalability were observed, highlighting its potential in the pharmaceutical and chemical industries.

Key words

benzo[c]isothiazole 2-oxide - sulfoximine - C–N cross-coupling reaction - copper-catalyzed - Ullmann reaction

Publication History

Received: 06 February 2025

Accepted after revision: 21 February 2025

Accepted Manuscript online:
21 February 2025

Article published online:
15 May 2025

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• 12 Cycloamidation Reaction; General Procedure: A 15 mL Schlenk tube was charged with 1 (0.2 mmol), CuI (0.01 mmol, 5 mol%), and Cs₂CO₃ (0.2 mmol, 1.0 equiv) in 1,4-dioxane (1.0 mL) and the mixture was stirred at 60 °C in oil bath under Ar atmosphere for 4 h. Upon completion of the reaction (as determined by TLC analysis), EtOAc (10 mL) was added to the solution, the mixture was washed with brine, and the aqueous layer was washed with EtOAc (2 × 5 mL). The combined organic phase was dried over Na₂SO₄ and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (EtOAc/hexane = 1:2) to afford target product 2.