Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysts

Organic Letters
Kiyofumi InamotoYoshinori Kondo

Abstract

In this study, a facile synthesis of 3-carboxylated indoles involving a tandem-type cyclization of 2-ethynylanilines and subsequent CO2 fixation at the 3-position of the indole ring is realized. The reaction proceeds efficiently at 65 °C under 10 atm of CO2, giving rise to variously substituted 3-carboxylated indoles, generally in high yields. An inorganic base, such as K2CO3, is the only reagent required, and the addition of transition metal catalysts is not necessary. The method provides a novel, simple, and promising strategy for CO2 fixation in the research field of heterocyclic chemistry.

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Citations

May 24, 2016·Organic Letters·Bukeyan MiaoShengming Ma
Oct 27, 2015·Journal of the American Chemical Society·Yusuke MasudaMasahiro Murakami
Sep 12, 2014·ChemSusChem·Bing Yu, Liang-Nian He
Jun 9, 2018·ChemSusChem·Alessio Cherubini-CelliXavier Companyó
Aug 1, 2019·Chemical Communications : Chem Comm·Yuta SadamitsuTohru Yamada
Feb 13, 2013·Beilstein Journal of Organic Chemistry·Maddi Sridhar ReddyMadala Haribabu
Oct 9, 2014·Chemical Communications : Chem Comm·Takuya SugaNobuharu Iwasawa
Jun 20, 2020·Organic & Biomolecular Chemistry·Jose S S Neto, Gilson Zeni
Dec 14, 2016·Topics in Current Chemistry·Xiao-Feng Wu, Feng Zheng
May 18, 2020·Chemistry, an Asian Journal·Takanobu SaitouNobuharu Iwasawa
Nov 27, 2018·Organic Letters·Tsuyoshi MitaYoshihiro Sato
Oct 6, 2012·Organic Letters·Woo-Jin YooShū Kobayashi
May 28, 2013·The Journal of Organic Chemistry·Maddi Sridhar ReddySurendra Puri

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