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

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20 Citations (Scopus)

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

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Biological Products
Amides
Amines
Butylamines
Ions
Pyrans
Kinetics
Lysine
Cations
Rate constants
perchlorate

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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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.",
author = "Katritzky, {Alan R.} and Mokrosz, {Jerzy L.} and {De Rosa}, Michael",
year = "1984",
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T1 - 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

AU - Katritzky, Alan R.

AU - Mokrosz, Jerzy L.

AU - De Rosa, Michael

PY - 1984/1/1

Y1 - 1984/1/1

N2 - 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.

AB - 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.

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