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通过芳炔与 3-重氮吲哚啉-2-酮和吲唑并[2,3-c]喹唑啉-6(5H)-酮的[3 + 2]偶极环加成反应及随后的热异构化合成螺[吲唑-3,3'-吲哚啉]-2'-酮

Synthesis of Spiro[indazole-3,3'-indolin]-2'-ones via [3 + 2] Dipolar Cycloaddition of Arynes with 3-Diazoindolin-2-ones and Indazolo[2,3-c]quinazolin-6(5H)-ones by Subsequent Thermal Isomerization.

机构信息

The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou 730000, China.

Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University , Shenzhen 518055, China.

出版信息

J Org Chem. 2017 Aug 4;82(15):8228-8233. doi: 10.1021/acs.joc.7b00990. Epub 2017 Jul 19.

Abstract

An efficient protocol for facile construction of spiro[indazole-3,3'-indolin]-2'-ones was developed via [3 + 2] dipolar cycloaddition of arynes with 3-diazoindolin-2-ones under mild conditions in excellent yields. Subsequent thermal isomerization of the spiro[indazole-3,3'-indolin]-2'-ones readily afforded indazolo[2,3-c]quinazolin-6(5H)-ones.

摘要

发展了一种高效的通过温和条件下芳炔与 3-重氮吲哚啉-2-酮的[3+2]偶极环加成反应来构建螺[吲唑-3,3'-吲哚啉]-2-酮的方法,该方法产率优异。随后,螺[吲唑-3,3'-吲哚啉]-2-酮的热异构化很容易得到吲唑并[2,3-c]喹唑啉-6(5H)-酮。

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