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铑(III)催化3-芳基喹喔啉-2(1)-酮与炔烃的螺环化反应:通往螺环喹喔啉酮的实用方法

Rh(iii)-catalyzed spiroannulation of 3-arylquinoxalin-2(1)-ones with alkynes: practical access to spiroquinoxalinones.

作者信息

Zhang Yuanfei, Huang Ting, Li Xinghua, Zhang Min, Song Ying, Huang Kelin, Su Weiping

机构信息

Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University Nanning 530001 China.

State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences Fuzhou 350002 China

出版信息

RSC Adv. 2020 Jun 10;10(37):22216-22221. doi: 10.1039/d0ra03348k. eCollection 2020 Jun 8.

DOI:10.1039/d0ra03348k
PMID:35516638
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9054490/
Abstract

The Rh(iii)-catalyzed synthesis of spiroquinoxalinone derivatives from 3-arylquinoxalin-2(1)-ones and alkynes a C-H functionalization/[3 + 2] annulation sequence has been developed. This method, featuring low catalyst loading, was amenable to Gram scale synthesis and tolerated a variety of functional groups and substitution patterns on the aryl rings, providing the target products in good to excellent yields.

摘要

已开发出一种由铑(III)催化的、从3-芳基喹喔啉-2(1)-酮和炔烃合成螺喹喔啉酮衍生物的方法,该方法是一种C-H官能团化/[3+2]环化序列。此方法催化剂负载量低,适用于克级规模的合成,并且能耐受芳环上的各种官能团和取代模式,以良好至优异的产率提供目标产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/ac84136d37a2/d0ra03348k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/950e48ac4abb/d0ra03348k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/a52a36314506/d0ra03348k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/56b8e0574f99/d0ra03348k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/06e3c6c5065e/d0ra03348k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/ac84136d37a2/d0ra03348k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/950e48ac4abb/d0ra03348k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/a52a36314506/d0ra03348k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/56b8e0574f99/d0ra03348k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/06e3c6c5065e/d0ra03348k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/451d/9054490/ac84136d37a2/d0ra03348k-s4.jpg

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本文引用的文献

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J Am Chem Soc. 2020 Mar 25;142(12):5531-5537. doi: 10.1021/jacs.0c01171. Epub 2020 Mar 12.
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A Rhodium-Catalyzed [3 + 2] Annulation of General Aromatic Aldimines/Ketimines and N-Substituted Maleimides.铑催化的通用芳基醛亚胺/酮亚胺和 N-取代马来酰亚胺的[3+2]环化反应。
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Rh(III)-Catalyzed Diastereodivergent Spiroannulation of Cyclic Imines with Activated Alkenes.
铑(III)催化的环状亚胺与活化烯烃的非对映选择性螺环化反应。
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Computational Studies of Carboxylate-Assisted C-H Activation and Functionalization at Group 8-10 Transition Metal Centers.第八族到第十族过渡金属中心羧酸辅助的 C-H 活化和功能化的计算研究。
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