Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles was written by Xie, Zengyang;Chen, Ruijiao;Ma, Mingfang;Kong, Lingdong;Liu, Jun;Wang, Cunde. And the article was included in Applied Organometallic Chemistry in 2019.Application of 15864-32-1 This article mentions the following:
An efficient and practical C-N bond formation methodol. for the synthesis of N-(alkyl)benzothiazoles I [R = H, 4-Me, 6-Br, etc.; R1 = n-Pr, Ph, 4-MeOC6H4, etc.] and N-(alkyl)thiazoles II [R2 = H, Me; R3 = Ph, 2-MeC6H4, 2-naphthyl, etc.; R2R3 = (CH2)5; R4 = H, 4-Me, 5-Me] was developed via Cu-catalyzed one-pot two-step cross-coupling of 2-aminobenzothiazoles/2-aminothiazoles and aldehydes/ketones with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups. A variety of functionalized benzothiazoles/thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-6-bromobenzothiazole (cas: 15864-32-1Application of 15864-32-1).
2-Amino-6-bromobenzothiazole (cas: 15864-32-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application of 15864-32-1
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica