Alkylation of quinolines with trialkyl phosphates. Part 2. Mechanistic studies

Judit Frank, Zoltán Mészáros, Tamás Kömives, Attila F. Márton, Ferenc Dutka

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The mechanism of alkylation of 4-quinolone (3) by trialkyl phosphates has been studied by preparative, kinetic, and isotopic methods, as welt as by u.v. spectrophotometry. In a kinetically controlled process the transient initial formation of 4-methoxyquinoline (4a) was established ; this was subsequently transformed by trimethyl phosphate to a quaternary N-methyl-4-methoxyquinolinium salt (6a). The latter catalyses the transformation of (4a) by intermolecular O→N methyl transfer to the more stable N-methyl-4-quinolone (5a). The end product is a mixture of (5a) and (6a). Their ratio is shifted at higher temperature in favour of (6a). This is due partly to differences in the temperature dependence of the individual reactions and partly to alkylation of (5a) by trimethyl phosphate at higher temperature. A mechanism for the alkylation reaction is proposed.

Original languageEnglish
Pages (from-to)401-406
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number2
DOIs
Publication statusPublished - 1980

ASJC Scopus subject areas

  • Chemistry(all)

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