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通过贝斯曼-大平试剂与亚甲基吲哚酮的碱介导[1,3] -偶极环加成反应,高效一锅法区域选择性合成3,3'-螺磷酰基吡唑-氧化吲哚骨架。

An efficient one pot regioselective synthesis of a 3,3'-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann-Ohira reagent with methyleneindolinones.

作者信息

Shelke Anil M, Suryavanshi Gurunath

机构信息

Chemical Engineering & Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, Maharashtra, India-411008.

出版信息

Org Biomol Chem. 2015 Aug 28;13(32):8669-75. doi: 10.1039/c5ob01020a. Epub 2015 Jul 16.

Abstract

A one pot, highly regioselective synthesis of racemic 3,3'-spiro-phosphonylpyrazole-oxindole by 1,3-dipolar cycloaddition of an in situ generated anion of dialkyl 1-diazomethylphosphonate from the Bestmann-Ohira reagent (BOR) & methyleneindolinones has been developed. The synthesis affords the highly functionalized pyrazole scaffolds in good yields with excellent regioselectivity under mild reaction conditions within a short reaction time.

摘要

通过由贝斯德曼-大平试剂(BOR)原位生成的二烷基1-重氮甲基膦酸酯阴离子与亚甲基吲哚酮进行1,3-偶极环加成反应,开发了一种一锅法、高区域选择性合成外消旋3,3'-螺-膦酰基吡唑-氧化吲哚的方法。该合成方法在温和的反应条件下、短反应时间内以良好的产率和优异的区域选择性提供了高度官能化的吡唑支架。

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