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一种用于合成C4-乙胺吲哚和C7-氨基二氢吲哚的可控碳消除的转换策略。

A switch strategy for the synthesis of C4-ethylamine indole and C7-aminoindoline controllable carbon elimination.

作者信息

Zhang Bo-Sheng, Deng Bao-Jie, Zhi Yuan-Xin, Guo Tian-Jiao, Wang Yi-Ming, Gou Xue-Ya, Quan Zheng-Jun, Wang Xi-Cun, Liang Yong-Min

机构信息

Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, College of Chemistry and Chemical Engineering, Northwest Normal University Lanzhou 730070 China

State Key Laboratory of Applied OrganicChemistry, Lanzhou University Lanzhou 730000 China.

出版信息

Chem Sci. 2024 Sep 6;15(39):16169-75. doi: 10.1039/d4sc05111d.

Abstract

Controllable β-carbon elimination to extrude norbornene remains a long-standing challenge in palladium and norbornene chemistry. Herein, this manuscript describes a switchable synthesis of biologically active C4-ethylaminoindole and C7-aminoindoline scaffolds by controlling β-carbon elimination, utilizing aziridine as a C-H ethylamination reagent through a C-N bond cleavage reaction. Furthermore, the protecting groups of the product can be easily removed, offering an unusual method for the synthesis of dopamine receptor agonists.

摘要

在钯和降冰片烯化学领域,可控的β-碳消除以挤出降冰片烯仍是一个长期存在的挑战。本文描述了一种通过控制β-碳消除,以氮丙啶作为C-H乙基化试剂,通过C-N键裂解反应,可切换合成生物活性C4-乙基氨基吲哚和C7-氨基吲哚啉支架的方法。此外,产物的保护基团可轻松去除,为多巴胺受体激动剂的合成提供了一种独特的方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66d1/11463288/c1a0c7770471/d4sc05111d-f1.jpg

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