A Cu2O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water was written by Zhang, Jinli;Chen, Ling;Dong, Yibo;Yang, Jinchen;Wu, Yangjie. And the article was included in Organic & Biomolecular Chemistry in 2020.Formula: C13H10N2S This article mentions the following:
An efficient approach to synthesize heteroaromatic 2-amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to synthesize heteroaromatic 2-amines in moderate to excellent yields. A plausible mechanism was proposed and the role of TBAB and Cu2O in the present strategy was suggested with the help of ESI mass spectrometry. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: C13H10N2S).
N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. 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.Formula: C13H10N2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica