Issue 78, 2016

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
09 jun 2016
Accepted
20 jul 2016
First published
22 jul 2016

RSC Adv., 2016,6, 74845-74858

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

B. K. Villuri, T. Kotipalli, V. kavala, S. S. Ichake, V. Bandi, C. Kuo and C. Yao, RSC Adv., 2016, 6, 74845 DOI: 10.1039/C6RA15002K

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