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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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.

Original language	English
Pages (from-to)	74845-74858
Number of pages	14
Journal	RSC Advances
Volume	6
Issue number	78
DOIs	https://doi.org/10.1039/c6ra15002k
Publication status	Published - 2016

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/c6ra15002k

Cite this

@article{9a57585808d14afdab2cd9a85b64f529,

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",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "78",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/84982171776

UR - https://www.scopus.com/pages/publications/84982171776#tab=citedBy

U2 - 10.1039/c6ra15002k

DO - 10.1039/c6ra15002k

M3 - Article

AN - SCOPUS:84982171776

SN - 2046-2069

VL - 6

SP - 74845

EP - 74858

JO - RSC Advances

JF - RSC Advances

IS - 78

ER -

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

Abstract

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CCDC 1484056: Experimental Crystal Structure Determination

CCDC 1484059: Experimental Crystal Structure Determination

CCDC 1484057: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 1484056: Experimental Crystal Structure Determination

CCDC 1484059: Experimental Crystal Structure Determination

CCDC 1484057: Experimental Crystal Structure Determination

Cite this