Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N -(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor

We developed an efficient method for synthesis of substituted -benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted -(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including -acetyl and -Ts substrates) and substituted indoles were obtained in good to excell...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-03, Vol.25 (5), p.1233
Main Authors: Chang, Zhe, Ma, Tong, Zhang, Yu, Dong, Zheng, Zhao, Heng, Zhao, Depeng
Format: Article
Language:English
Subjects:
Benzamide
Benzamides - chemical synthesis
Benzamides - chemistry
Benzoxazines
c-h functionalization
Catalysis
Chromatography
Communication
Cyclization
indole
Indoles
Indoles - chemical synthesis
Indoles - chemistry
Indomethacin
Indomethacin - chemical synthesis
Indomethacin - chemistry
Methods
Palladium
Palladium - chemistry
Selectivity
Substitutes
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We developed an efficient method for synthesis of substituted -benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted -(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including -acetyl and -Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for -benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted -benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25051233