Coproduct Promoted Povarov Reaction: Synthesis of Substituted Quinolines from Methyl Ketones, Arylamines, and α-Ketoesters

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2015 May 15

PMID 25973528

Citations 7

Authors

Qinghe Gao

Shan Liu

Xia Wu

Jingjing Zhang

Anxin Wu

Affiliations

Soon will be listed here.

Abstract

A highly efficient I2-catalyzed Povarov-type reaction of methyl ketones, arylamines, and α-ketoesters is developed. This reaction utilizes a catalytic amount of HI coproduct as a promoter for the synthesis of substituted quinolones. This simple procedure represents an interesting new form of reactivity for the Povarov reaction with good functional group compatibility.

Citing Articles

Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.

Wu J, Tan X, Wu W, Jiang H Nat Commun. 2024; 15(1):6776.

PMID: 39117681 PMC: 11310316. DOI: 10.1038/s41467-024-51173-4.

Aryl Methyl Ketones: Versatile Synthons in the Synthesis of Heterocyclic Compounds.

Mohammed S, West J, Mitton-Fry M SynOpen. 2023; 6(2):110-131.

PMID: 37206085 PMC: 10195057. DOI: 10.1055/a-1826-2852.

Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review.

Weyesa A, Mulugeta E RSC Adv. 2022; 10(35):20784-20793.

PMID: 35517753 PMC: 9054321. DOI: 10.1039/d0ra03763j.

Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5-chromeno[2,3-]pyridin-5-yl)malonic Acids in DMSO.

Ryzhkova Y, Elinson M, Maslov O, Fakhrutdinov A Molecules. 2021; 26(22).

PMID: 34833930 PMC: 8624304. DOI: 10.3390/molecules26226839.

Mo-Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties.

Hernandez-Ruiz R, Rubio-Presa R, Suarez-Pantiga S, Pedrosa M, Fernandez-Rodriguez M, Tapia M Chemistry. 2021; 27(54):13613-13623.

PMID: 34288167 PMC: 8518888. DOI: 10.1002/chem.202102000.