2‐Amino‐4‐arylthiazoles through One‐Pot Transformation of Alkylarenes with NBS and Thioureas. Issue 14 (2nd April 2019)

• Record Type: Journal Article
• Authors: Shibasaki, Kaho; Togo, Hideo
• Is Part Of: European journal of organic chemistry. Issue 14(2019)
• Page Start: 2520
• Page End: 2527
• Publication Date: 2019-04-02
• Subjects: Heterocycles -- Thiazoles -- Cyclization -- One‐pot reactions -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900100
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Various alkylarenes were successfully transformed into the corresponding 2‐amino‐4‐arylthiazoles and 2, 4‐diarylthiazoles in good to moderate yields by the treatment with NBS, followed by the reaction with thioureas or arenethioamides.