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

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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 languageEnglish
Pages (from-to)74845-74858
Number of pages14
JournalRSC Advances
Volume6
Issue number78
DOIs
Publication statusPublished - 2016 Jan 1

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Villuri, B. K., Kotipalli, T., Kavala, V., Ichake, S. S., Bandi, V., Kuo, C. W., & Yao, C. F. (2016). Synthesis of spiro isoindolinone-indolines and 1,2-disubstituted indoles from 2-iodobenzamide derivatives. RSC Advances, 6(78), 74845-74858. https://doi.org/10.1039/c6ra15002k