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

Department of Chemistry

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

8 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 Jan 1

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

Access to Document

10.1039/c6ra15002k

Fingerprint Dive into the research topics of 'Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives'. Together they form a unique fingerprint.

Cite this

Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives. / Villuri, Bharath Kumar; Kotipalli, Trimurtulu; Kavala, Veerababurao; Ichake, Sachin S.; Bandi, Vijayalakshmi; Kuo, Chun Wei; Yao, Ching Fa.

In: RSC Advances, Vol. 6, No. 78, 01.01.2016, p. 74845-74858.

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

@article{f7bf4d8dc119400c87066a9f59ee0999,

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}",

year = "2016",

month = jan,

day = "1",

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 - 2016/1/1

Y1 - 2016/1/1

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 - http://www.scopus.com/inward/record.url?scp=84982171776&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84982171776&partnerID=8YFLogxK

U2 - 10.1039/c6ra15002k

DO - 10.1039/c6ra15002k

M3 - Article

AN - SCOPUS:84982171776

VL - 6

SP - 74845

EP - 74858

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 78

ER -