Work

A imple oute to 7-ubstituted Quinolin-2()-ones from -ubstituted nilines

Year: 2025

Type: article

Abstract: Meta -substituted anilines are condensed with methyl 3,3-dimethoxypropionate in a two-step acylation, cyclization sequence to preferentially form 7-substituted quinolinones in an isomeric mixture with 5-substituted quinolinones. The product ratios in this previously unexplored class of substrates depend on the steric and electronic properties of the aniline substituent. Within a series of halogenated anilines, selectivity varies directly with electronegativity and inversely with C–X bond length, up to 93:7 (R = F). For alkyl substituted anilines, a Charton analysis reveals a linear free-energy relationship between steric bulk of the alkyl substituent and selectivity for 7-substituted products, where selectivity for 7-substituted products increases with steric bulk of the alkyl substituent. Alkyl substituted quinolinones are generated with up to 97:3 selectivity for the 7-substituted product when R = t Bu.

Source: Results in Chemistry

DOI: 10.1016/j.rechem.2025.102089

Authors: Marisol Varela Ausec, Mary K. Payne, Jason R. Stewart, Olivia M. Galando, Eliott J. Wright, Sara E.S. Martin

Institution: College of Wooster

Language: English

Topic: Synthesis and Reactivity of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,870

Funders: National Science Foundation, College of Wooster