Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor

[摘要] A novel approach to the synthesis of 2-cyano-6-methoxybenzothiazole via the Cu-catalyzed cyanation of 2-iodo-6-methoxybenzothiazole was developed. K 4 [Fe(CN) 6 ] was used as a source of cyanide, and a Cu/N,N,N′,N′-tetramethylethylenediamine (TMEDA) system was utilized as a catalyst. This approach is scalable and can be practiced with operational benign. The most stable conformation of 2-cyano-6-methoxybenzothiazole was delineated using the density functional theory (DFT)/B3LYP method with 6-311++G(d, p) basis set.

[学科分类] 内科医学

[关键词] 2-cyano-6-methoxybenzothiazole;2-iodo-6-methoxyenzothiazole;Cu catalyst;cyanation;DFT;firefly luciferin;K4[Fe(CN)6]