Pd-Catalyzed De Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 22

PMID 31433186

Citations 4

Authors

Qian Wang

Angelina Osipyan

Markella Konstantinidou

Roberto Butera

Kumchok C Mgimpatsang

Svitlana V Shishkina

Alexander Domling

Affiliations

Soon will be listed here.

Abstract

Here we describe a facile, tandem synthetic route for indolo[3,2-]quinolinones, a class of natural alkaloid analogues of high biological significance. A Ugi four-component reaction with indole-2-carboxylic acid and an aniline followed by a Pd-catalyzed cyclization yields tetracyclic indoloquinolines in good to moderate yields. Commercially available building blocks yield highly diverse analogues in just two simple steps.

Citing Articles

Access to Isoquinolin-2(1)-yl-acetamides and Isoindolin-2-yl-acetamides from a Common MCR Precursor.

Li X, Wang Q, Zheng Q, Kurpiewska K, Kalinowska-Tluscik J, Domling A J Org Chem. 2022; 87(21):14463-14475.

PMID: 36282152 PMC: 9639002. DOI: 10.1021/acs.joc.2c01905.

Isoquinolone-4-Carboxylic Acids by Ammonia-Ugi-4CR and Copper-Catalyzed Domino Reaction.

Wang Q, Mgimpatsang K, Li X, Domling A J Org Chem. 2021; 86(14):9771-9780.

PMID: 34184894 PMC: 8291606. DOI: 10.1021/acs.joc.1c01170.

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones.

Hong W, Shin I, Lim H Molecules. 2020; 25(22).

PMID: 33233747 PMC: 7699938. DOI: 10.3390/molecules25225450.

Copper-Catalyzed Modular Assembly of Polyheterocycles.

Wang Q, Tuinhof J, Mgimpatsang K, Kurpiewska K, Kalinowska-Tluscik J, Domling A J Org Chem. 2020; 85(15):9915-9927.

PMID: 32615764 PMC: 7418108. DOI: 10.1021/acs.joc.0c01238.

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