Pyrylium-mediated transformations of natural products. Part 2. Reaction of 4-(4-methoxy-3-sulphophenyl)-2,6-bis-(4-sulphophenyl)pyrylium perchlorate with primary amines
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 849-855
- https://doi.org/10.1039/p29840000849
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.Keywords
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