Rapid synthesis of a ~13C_6-benzothiazolium salt from ~13C_6-aniline

摘要

~13C_6-labeled aniline was used as a starting material for the facile synthesis of ~13C_6-benzothiazolium salt (1). Introduction:The chemistry of benzothiazolium salts generated by alkylation of benzothiazole thiones has been studied significantly. These salts have been reported to inhibit nitric oxide production and in the treatment of coronaviril infection, and are also useful intermediates in the synthesis of bioactive 2-imino-benzothia-zolines. The hydrolysis of these salts can be effected under a variety of conditions leading to exclusively N-alkyl substituted benzothiazoline structures which are useful building blocks in the synthesis of compounds containing this heterocyclic motif.4 The synthesis of the benzothiazolium salts is readily achieved by double alkylation of an appropriate ambidentate electrophile by benzothiazole thione (2). 2 is itself an important accelerator in the vulcanization of rubber among other applications. Additionally, 2 has been utilized as a convenient leaving group for the introduction of the Fmoc-protecting group (Figure 1).