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铜(0)/PPh 介导的 -硝基炔与甲基酮肟的双杂环化反应,构建吡唑并[3,4-d]吲哚。

Copper(0)/PPh-Mediated Bisheteroannulations of -Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls.

机构信息

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.

出版信息

Org Lett. 2020 Aug 7;22(15):6117-6121. doi: 10.1021/acs.orglett.0c02180. Epub 2020 Jul 20.

DOI:10.1021/acs.orglett.0c02180
PMID:32686941
Abstract

A copper(0)/PPh-mediated cascade bisheteroannulation reaction of -nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.

摘要

一种铜(0)/PPh 介导的 -硝基炔烃与甲基酮肟的级联双杂环化反应已经被开发出来,为合成多种吡唑并融合的伪吲哚类化合物提供了可行的途径。包括敏感的 C-I 键在内的合成上有用的官能团与该体系兼容。机理研究表明,该反应经历了 PPh 介导的脱氧环化异构化和铜催化的[3+2]吡唑环化的级联反应。

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Org Lett. 2020 Aug 7;22(15):6117-6121. doi: 10.1021/acs.orglett.0c02180. Epub 2020 Jul 20.
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