One‐Pot Synthesis of N‐Benzyl/Allyl‐N‐phenyl‐2‐benzothiazolamines from 1‐(2‐Iodophenyl)‐3‐phenylthioureas and Benzyl/Allyl Halides

• Published in: European journal of organic chemistry 2023-02, Vol.26 (6), p.n/a
• Main Authors: Feng, Rong, Ma, Jie, Dong, Zhi‐Bing
• Format: Article
• Language: English
• Subjects: 2-aminobenzothiazoles; Chemical synthesis; copper; C−N bond; Halides; one-pot; Phenylthiourea; Substrates; synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202201145

A facile method for the copper‐catalyzed synthesis of N‐benzyl‐N‐phenyl‐2‐benzothiazolamines was explored. In the presence of CuI, N‐phenylbenzothiazolamines was in situ generated from substituted 1‐(2‐iodophenyl)‐3‐phenylthioureas, which susequently underwent coupling with benzyl/allyl halides to give the desired N‐benzyl/allyl‐N‐phenyl‐2‐benzothiazolamines fluently in a one‐pot manner. The protocol features easy performance, easily available materials, good yield and broad substrates scope, showing potential synthetic value for the preparation of a variety of biologically or pharmaceutically active compounds. A series of N‐benzyl/allyl‐N‐phenyl‐2‐benzothiazolamines were obtained smoothly from 1‐(2‐Iodophenyl)‐3‐phenylthioureas and benzyl/allyl halides via one‐pot manner. The protocol features easily available starting materials, easy performance, mild reaction conditions, good yields and broad substrates scope, illustrating its synthetic value for the synthesis of a diversity of biologically or pharmaceutically active compounds.