期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 8, 页码 1590-1596出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101684
关键词
Alkenes; Reaction mechanisms; Regioselectivity; Sulfur heterocycles; Synthetic methods
资金
- National Natural Science Foundation of China [20972147, 20732006]
- National Basic Research Program of China (973 Program) [2010CB833300]
Depending on their structures, imines are able to undergo either olefination or vicinal difunctionalization with various a-(benzothiazol-2-ylsulfonyl) carbonyl compounds in the absence of external bases. The olefination reaction of aromatic imines with alpha-(benzothiazol-2-ylsulfonyl) carbonyl compounds proceeds smoothly in tetrahydrofuran at 70 degrees C to give structurally diverse alpha, beta-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 alpha,beta-unsaturated imines are subjected to regiospecific vicinal difunctionalization with alpha-(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.
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