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Synlett 2000; 2000(12): 1831-1833
DOI: 10.1055/s-2000-8697
DOI: 10.1055/s-2000-8697
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Convenient Synthesis of (±)2-Thiazolidine Acetic Acid Derivatives by Ring Contraction of 1,4-Thiazepine Derivatives
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Publication History
Publication Date:
31 December 2000 (online)
The ring contraction of 1,4-thiazepine derivatives into methyl ester as well as anilides of (±)2-(thiazolidine-4-on)-acetic acid derivatives is reported. The new procedure involves CAN oxidation of 1,4-thiazepine derivatives in methanol or acetonitrile to give rearrangement of seven membered ring of 1,4-thiazepine to 2-thiazolidine acetic acid derivatives 3 and 4. This process can be carried out as one-pot reaction.
ring contractions - thiazepine - thiazolidine - rearrangements - oxidations