2‐Amino‐4‐arylthiazoles through One‐Pot Transformation of Alkylarenes with NBS and Thioureas

Abstract

Treatment of alkylarenes with N‐bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2‐amino‐ 4‐arylthiazoles or 2,4‐diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one‐pot transformation method of alkylarenes into 2‐amino‐4‐arylthiazoles and 2,4‐diarylthiazoles directly under mild and transition‐metal‐free conditions.

Sulfur‐Centered Radicals in Visible Light Isocyanide Photochemistry

“…While visible light photoredox reactions involving thioketones, thioamides, and benzothioates mainly afforded desulfurization products [67,68] and heterocyclic compounds such as thiazoles [69] and thiadiazoles, [70,71] the current section will highlight the handful of transformations harnessing C=S containing compounds to form C-centered radicals, such as xanthates and Nhydroxy-2-thiopyridones.…”

Harnessing Diazoketones for the Efficient Synthesis of 2,4-Disubstituted-(1,3)Thiazoles: Scalable and Versatile Approach to Important Heterocyclic Scaffolds

“…The shift to multicomponent, one-pot reactions signified a major advancement towards sustainability and efficiency in thiazole synthesis. The choice of solvent, a critical aspect of reaction efficiency and environmental impact, became a focal point, with solvent-mediated reactions gaining prominence [47][48][49][50][51][52][53] . Also the recent method for regioselective synthesis of substituted thiazoles from chromone derivatives and thioamides, is worth mentioning in the context 54 .…”

Enhancing C–S and C–N bond formation with ultrasound assistance: lipase-catalyzed synthesis of 2,4-disubstituted thiazole derivatives from arylethanones and thioamides

“…1. 11,12 The existence of these patterns in natural substances and their diverse biological functions has sparked interest in synthesizing them. 13,14 Nowadays, there are numerous methods for the synthesis of thiazole moiety.…”