Electrosynthesis of 2,4-Disubstituted Quinolines via Formal (5+1) Cycloaddition

Talukder, Angshuman (2025) Electrosynthesis of 2,4-Disubstituted Quinolines via Formal (5+1) Cycloaddition. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Angshuman Talukder (20MS005)) 20MS005_Thesis_file.pdf Restricted to Repository staff only Download (9MB)

Abstract

A novel electrochemical cycloaddition method utilizing HAT is reported for creating a Quinoline-2,4-dicarboxylate framework. Various functional groups demonstrate good compatibility within this metal-free, mild, and scalable electro-redox process. Mechanistic analysis suggest that the chloride radical functions as a hydrogen atom transfer (HAT) agent, enabling the transformation of the oxidized N-aryl alaninate intermediate into the corresponding enamine species, which subsequently undergoes a (5 + 1) cycloaddition with the imine intermediate produced electrochemically, resulting in the formation of C−C bonds, followed by tautomerization, additional oxidation, and aromatization that leads to the biologically relevant six-membered quinoline core.

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