A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates. Issue 54 (16th June 2016)

• Record Type: Journal Article
• Authors: He, Yimiao; Li, Jing; Luo, Shuang; Huang, Jinbo; Zhu, Qiang
• Is Part Of: Chemical communications. Volume 52:Issue 54(2016)
• Page Start: 8444
• Page End: 8447
• Publication Date: 2016-06-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc04394a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Abstract : A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n -Bu4 NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.