Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives

Bharath Kumar Villuri; Trimurtulu Kotipalli; Veerababurao Kavala; Sachin S. Ichake; Vijayalakshmi Bandi; Chun Wei Kuo; Ching Fa Yao

doi:10.1039/c6ra15002k

Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives

Bharath Kumar Villuri, Trimurtulu Kotipalli, Veerababurao Kavala, Sachin S. Ichake, Vijayalakshmi Bandi, Chun Wei Kuo, Ching Fa Yao^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

14 引文斯高帕斯（Scopus）

摘要

Copper catalyzed C-terminal and N-terminal attack of 2-alkynylanilines to 2-iodobenzamides afforded isoindolinones and 1,2-disubstituted indoles, respectively. Further, the isoindolinone derivatives were converted to spiro fused isoindolinone-indolines utilizing a halonium ion mediated strategy using NBS/TCC in the presence of acetic anhydride. Also, the ortho effect of the amide group in 2-iodobenzamide has been successfully applied for the synthesis of 1,2-disubstituted indoles.

原文	英語
頁（從 - 到）	74845-74858
頁數	14
期刊	RSC Advances
卷	6
發行號	78
DOIs	https://doi.org/10.1039/c6ra15002k
出版狀態	已發佈 - 2016

ASJC Scopus subject areas

一般化學
一般化學工程

存取文件

10.1039/c6ra15002k

其它文件與鏈接

CCDC 1484061: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Kotipalli, T. (Creator), Kavala, V. (Creator), Ichake, S. S. (Creator), Bandi, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1lt8ym, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt8ym&sid=DataCite
資料集: Dataset
CCDC 1484060: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Kotipalli, T. (Creator), Kavala, V. (Creator), Ichake, S. S. (Creator), Bandi, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1lt8xl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt8xl&sid=DataCite
資料集: Dataset
CCDC 1484057: Experimental Crystal Structure Determination
Villuri, B. K. (Creator), Kotipalli, T. (Creator), Kavala, V. (Creator), Ichake, S. S. (Creator), Bandi, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2016
DOI: 10.5517/ccdc.csd.cc1lt8th, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lt8th&sid=DataCite
資料集: Dataset

引用此

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title = "Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives",

abstract = "Copper catalyzed C-terminal and N-terminal attack of 2-alkynylanilines to 2-iodobenzamides afforded isoindolinones and 1,2-disubstituted indoles, respectively. Further, the isoindolinone derivatives were converted to spiro fused isoindolinone-indolines utilizing a halonium ion mediated strategy using NBS/TCC in the presence of acetic anhydride. Also, the ortho effect of the amide group in 2-iodobenzamide has been successfully applied for the synthesis of 1,2-disubstituted indoles.",

author = "Villuri, {Bharath Kumar} and Trimurtulu Kotipalli and Veerababurao Kavala and Ichake, {Sachin S.} and Vijayalakshmi Bandi and Kuo, {Chun Wei} and Yao, {Ching Fa}",

note = "Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6ra15002k",

language = "English",

volume = "6",

pages = "74845--74858",

journal = "RSC Advances",

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T1 - Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives

AU - Villuri, Bharath Kumar

AU - Kotipalli, Trimurtulu

AU - Kavala, Veerababurao

AU - Ichake, Sachin S.

AU - Bandi, Vijayalakshmi

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2016

Y1 - 2016

N2 - Copper catalyzed C-terminal and N-terminal attack of 2-alkynylanilines to 2-iodobenzamides afforded isoindolinones and 1,2-disubstituted indoles, respectively. Further, the isoindolinone derivatives were converted to spiro fused isoindolinone-indolines utilizing a halonium ion mediated strategy using NBS/TCC in the presence of acetic anhydride. Also, the ortho effect of the amide group in 2-iodobenzamide has been successfully applied for the synthesis of 1,2-disubstituted indoles.

AB - Copper catalyzed C-terminal and N-terminal attack of 2-alkynylanilines to 2-iodobenzamides afforded isoindolinones and 1,2-disubstituted indoles, respectively. Further, the isoindolinone derivatives were converted to spiro fused isoindolinone-indolines utilizing a halonium ion mediated strategy using NBS/TCC in the presence of acetic anhydride. Also, the ortho effect of the amide group in 2-iodobenzamide has been successfully applied for the synthesis of 1,2-disubstituted indoles.

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Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1484061: Experimental Crystal Structure Determination

CCDC 1484060: Experimental Crystal Structure Determination

CCDC 1484057: Experimental Crystal Structure Determination

引用此