Synthesis of N-Substituted-2-Aminobenzothiazoles by Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of 2-Haloanilines with Isothiocyanates

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 34; pp. 5897 - 5901
• Main Authors: Shen, Guodong, Lv, Xin, Bao, Weiliang
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.12.2009; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Chemistry; Chemistry, Organic; Copper; Cross-coupling; Domino reactions; Exact sciences and technology; Fused-ring systems; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Hetero­cycles; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; BENZOTHIAZOLE; Heterocycles; ANALOGS; ARYLATION; EFFICIENT SYNTHESIS; 2-AMINOBENZOTHIAZOLES; Cross-coupling; Domino reactions; N BOND FORMATION; INHIBITORS; Copper; DERIVATIVES; Fused-ring systems; Sulfur nitrogen heterocycle; Catalytic reaction; Mild operating conditions; Ligand; Aniline derivatives; Benzothiazole derivatives; Chemical coupling; Amine; Organic isothiocyanate; Cross reaction; Benzenic compound; Copper I; Copper I Iodides; Chemical synthesis; Successive reaction
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200900953

A novel and efficient formation of N‐substituted‐2‐aminobenzothiazoles by a ligand‐free copper(I)‐catalyzed one‐pot cascade process was developed. A variety of isothiocyanates coupled with 2‐iodoanilines to give N‐substituted‐2‐aminobenzothiazoles in moderate to excellent yields under mild conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) A novel and efficient formation of N‐substituted‐2‐aminobenzothiazoles by a ligand‐free copper(I)‐catalyzed one‐pot cascade process was developed. Various N‐substituted‐2‐aminobenzothiazoles, whichmight be potentially applicable in the pharmaceutical and biochemical areas, were conveniently synthesized in moderate toexcellent yields.