Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles was written by Jin, Lvnan;Zhou, Xuan;Zhao, Yunbo;Guo, Jing;Stephan, Douglas W.. And the article was included in Organic & Biomolecular Chemistry in 2022.Electric Literature of C7H4ClNOS This article mentions the following:
The chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles were achieved using B(C6F5)3, Rh2(OAc)4 or TfOH as the catalyst. This afforded routes to 54 benzothiazole derivatives These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Bronsted acid catalyzes. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Electric Literature of C7H4ClNOS).
6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Electric Literature of C7H4ClNOS
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica