2,5-二氢苯并[f][1,2,5]噻二氮杂卓1,1-二氧化物的环收缩：通向4H-苯并[b][1,4]噻嗪1,1-二氧化物
Ring contraction of 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides: access to 4H-benzo[b][1,4]thiazine 1,1-dioxides.
作者信息
Fülöpová Veronika, Krchňáková Anna, Schütznerová Eva, Zajíček Jaroslav, Krchňák Viktor
机构信息
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacky University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
出版信息
J Org Chem. 2015 Feb 6;80(3):1795-801. doi: 10.1021/jo502713k. Epub 2015 Jan 22.
We report an efficient synthesis of 4H-benzo[b][1,4]thiazine 1,1-dioxides via unprecedented ring contraction of 2,5-dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides under mild conditions involving carbon-sulfur bond formation. 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-dioxides are easily accessible from commercially available building blocks, including Fmoc-protected amino acids, 2-nitrobenzenesulfonyl chlorides, and bromo ketones. Benzothiazine 1,1-dioxides represent pharmacologically relevant derivatives with biological, medicinal, and industrial applications.
我们报道了一种通过2,5-二氢苯并[f][1,2,5]噻二氮杂卓1,1-二氧化物在温和条件下前所未有的环收缩反应高效合成4H-苯并[b][1,4]噻嗪1,1-二氧化物的方法，该反应涉及碳-硫键的形成。2,5-二氢苯并[f][1,2,5]噻二氮杂卓1,1-二氧化物可通过市售的起始原料轻松制备，包括Fmoc保护的氨基酸、2-硝基苯磺酰氯和溴代酮。苯并噻嗪1,1-二氧化物是具有生物学、医学和工业应用的药理学相关衍生物。
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