Pyrylium-mediated transformations of natural products. Part 2.1 reaction of 4-(4-methoxy-3-sulphophenyl)-2,6-bis-(4-sulphophenyl)-pyrylium perchlorate with primary amines

Alan R. Katritzky, Jerzy L. Mokrosz, Michael De Rosa

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

The title pyrylium cation reacts with amines in aqueous solution to give mixtures of divinylogous amide and pseudobase. The two products are formed by kinetic control in quantities which then slowly come to equilibrium. Further pyridinium ion is formed slowly from pseudobase. The divinylogous amide cyclises to pyridinium ion. Kinetic rate constants are described for reactions with lysine and other typical primary amines. With s-butylamine appreciable quantities of the 2H-pyran are formed.

Original languageEnglish (US)
Pages (from-to)849-855
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number5
DOIs
StatePublished - Jan 1 1984

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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