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3-硝基吲哚作为以氮为中心的亲核试剂用于对醌甲基化物的氮杂-1,6-迈克尔加成反应。

3-Nitroindoles Serving as -Centered Nucleophiles for Aza-1,6-Michael Addition to -Quinone Methides.

作者信息

Zhao Jian-Qiang, Wang Wen-Jie, Zhou Shun, Xiao Qi-Lin, Xue Xi-Sha, Zhang Yan-Ping, You Yong, Wang Zhen-Hua, Yuan Wei-Cheng

机构信息

Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

出版信息

Molecules. 2023 Jul 20;28(14):5529. doi: 10.3390/molecules28145529.

DOI:10.3390/molecules28145529
PMID:37513401
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10384903/
Abstract

An unprecedented -alkylation of 3-nitroindoles with -quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse -diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent -centered nucleophiles to react with -hydrophenyl -QMs for construction of various -diarylmethylindoles.

摘要

首次开发了3-硝基吲哚与醌甲基化物的前所未有的α-烷基化反应。以碳酸钾为碱，通过保护基迁移/ -1,6-迈克尔加成序列，以中等至良好的产率获得了一系列结构多样的α-二芳基甲基吲哚衍生物。对照实验也证明了反应过程。与之前3-硝基吲哚作为被各种亲核试剂捕获的亲电试剂的进展不同，本文的反应特点是3-硝基吲哚被定义为具有潜在α-中心亲核试剂，与α-氢苯基醌甲基化物反应以构建各种α-二芳基甲基吲哚。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/c60562df4c87/molecules-28-05529-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/e4caf1a91aa7/molecules-28-05529-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/0493144b1e77/molecules-28-05529-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/23972db4c194/molecules-28-05529-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/2472c37b399c/molecules-28-05529-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/4a94f79e2f4b/molecules-28-05529-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/3ee2324fa716/molecules-28-05529-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/c60562df4c87/molecules-28-05529-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/e4caf1a91aa7/molecules-28-05529-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/0493144b1e77/molecules-28-05529-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/23972db4c194/molecules-28-05529-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/2472c37b399c/molecules-28-05529-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/4a94f79e2f4b/molecules-28-05529-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/3ee2324fa716/molecules-28-05529-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6575/10384903/c60562df4c87/molecules-28-05529-g001.jpg

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本文引用的文献

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Direct Catalytic Asymmetric and Regiodivergent N1- and C3-Allenylic Alkylation of Indoles.吲哚的直接催化不对称和区域发散 N1-和 C3-烯丙基烷基化反应。
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Diastereoselective synthesis of polycyclic indolines dearomative [4 + 2] cycloaddition of 3-nitroindoles with -aminophenyl -quinone methides.
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Facile construction of dibenzodioxo[3.3.1]nonanes bearing spirocyclohexadienones domino [4 + 2] cycloaddition/C(sp)-H oxidative dehydrogenation coupling reactions.含螺环己二烯酮的二苯并二氧杂[3.3.1]壬烷的简便构建：多米诺[4 + 2]环加成/C(sp)-H氧化脱氢偶联反应
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