Synthesis of 2,4-Disubstituted Quinolines by Reactions of o-Isocyano-β-methoxystyrene Derivatives with Organolithiums

Abstract

Alkyl(or aryl)lithiums reacted efficiently with o-isocyano-β-methoxystyrene derivatives, prepared in three steps from o-aminophenyl ketones, to afford the corresponding 2,4-disubstituted quinolines in satisfactory yields.

Visible Light‐Promoted Three‐Component Reaction for the Synthesis of Fluoroalkyl‐Substituted Amides from Isocyanides

“…The authors have cited additional references within the Supporting Information. [16,17] Liaoning Province (Nos. 2022MS361 and 2021BS249) and the Research Project Fund of Liaoning Provincial Department of Education (Nos.…”

Silver-Catalyzed Nucleophilic Addition of β-Dicarbonyls to Isocyano Group: Facile Access to Indolin-3-ol Derivatives

“…A few examples of reaction with highly reactive organometallic nucleophiles such as Grignard reagents, , organolithiums, and organozincs were documented to date. The reaction of o -alkynylaryl isocyanides with nucleophiles to generate quinolines by a tandem nucleoaddition and cyclization sequence was documented . Additionally, the electrophilicity of isocyanides can also be activated by Lewis acid in some insertion reactions .…”

A convenient synthesis of quinolines by reactions of o-isocyano-β-methoxystyrenes with nucleophiles

“…3 Therefore, a large number of general methods for the preparation of substituted quinolines have recently been reported, 4 and any new general route to quinoline derivatives is of interest and value. In this paper we wish to report in full on the results of our investigation, 5,6 which offer a simple and general method for preparing 2,4-disubstituted quinolines and 4-substituted N,N-dialkylquinolin-2-amines by reactions of o-isocyano-b-methoxystyrenes with alkyl(or aryl)lithiums and lithium dialkylamides, respectively. 7 2-Alkylated quinoline derivatives 8 and quinolin-2-amines 9 have been reported to exhibit notable biological activities.…”