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Synthesis of 9-nitro-5H-spiro[benzo[b]tetrazolo[1,5-d][1,4]oxazepine-4,2′-oxirane] via an unusual ring-expansion
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2018-10-10 , DOI: 10.1016/j.tetlet.2018.10.016
Rao Kolluri , Jing Zhang , Rajinder Singh , Matthew A.J. Duncton

Attempted cyclization of (4-(hydroxymethyl)-8-nitro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazin-4-yl)methyl 4-methylbenzenesulfonate 2 did not give the expected spirooxetane product 1, but instead provided 9-nitro-5H-spiro[benzo[b]tetrazolo[1,5-d][1,4]oxazepine-4,2′-oxirane] 3 via an unusual ring-expansion process. The structure of compound 3 was confirmed by single-crystal X-ray crystallography. The spiroepoxide (oxirane) in compound 3 could be ring-opened with a variety of nucleophiles to give products of potential interest to medicinal chemists.



中文翻译:

通过不寻常的扩环合成9-硝基-5 H-螺[苯并[ b ]四唑并[1,5- d ] [1,4]氧杂氮杂-4,2'-环氧乙烷]

的尝试环化(4-(羟甲基)-8-硝基-4- ħ -苯并[ b ]四唑并[1,5- d ] [1,4]恶嗪-4-基)甲基4-甲基苯磺酸酯2没有给出预期螺氧杂环丁烷产物1,但通过不寻常的扩环过程提供了9-硝基-5 H-螺[苯并[ b ]四唑[1,5- d ] [1,4]奥氮平-4,2'-环氧乙烷] 3 。化合物3的结构通过单晶X射线晶体学确认。化合物3中的螺环氧化物(环氧乙烷)可以用各种亲核试剂进行开环,以使药物化学家可能感兴趣的产品。

更新日期:2018-10-10
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