1370463-40-3Relevant academic research and scientific papers
Stereoselective olefination and regiospecific vicinal difunctionalization of imines with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds
Shao, You-Dong,Wu, Xue-Song,Tian, Shi-Kai
supporting information; experimental part, p. 1590 - 1596 (2012/05/07)
Depending on their structures, imines are able to undergo either olefination or vicinal difunctionalization with various α-(benzothiazol-2- ylsulfonyl) carbonyl compounds in the absence of external bases. The olefination reaction of aromatic imines with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds proceeds smoothly in tetrahydrofuran at 70 °C to give structurally diverse α,β-unsaturated esters, amides, and ketones in good to excellent yields and with extremely high (E) selectivity. In contrast, the carbon-nitrogen double bonds of cyclic imines and the carbon-carbon double bonds of α,β-unsaturated imines are subjected to regiospecific vicinal difunctionalization with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds under the same reaction conditions to give a variety of benzothiazole derivatives in good to excellent yields. It is noteworthy that the benzothiazole moiety is present in a number of antitumor agents and bioluminescent molecules. In addition, plausible reaction pathways have been proposed to account for these transformations, and these are substantially supported by ESI-MS analysis of the reaction mixtures.
