Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation

Csaba Fehér, Ivan Habuš, Johan Wouters, Rita Skoda-Földes

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The palladium-catalyzed carbonylation of iodoferrocene was investigated in the presence of 2-aminopyrimidine derivatives as nucleophiles. 2-Amino-4-hydroxy-6-methylpyrimidine was found to act both as an O- and an N-nucleophile, leading to an ester and an amide derivative, respectively. Together with other spectroscopic methods, the structure of both products was proved by X-ray crystallography. 2-(Ferrocenoylamino)-4-chloro-6-alkylpyrimidines were obtained during carbonylation of iodoferrocene and 2-amino-4-chloro-6-alkylpyrimidines. The formation of a dimeric product via two subsequent carbonylation steps was also observed. The products may have practical importance as electrochemically detectable biosensors or building blocks for supramolecular assemblies.

Original languageEnglish
Pages (from-to)1981-1986
Number of pages6
JournalMonatshefte fur Chemie
Volume145
Issue number12
DOIs
Publication statusPublished - Sep 4 2014

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Carbonylation
Nucleophiles
Derivatives
X ray crystallography
Palladium
Biosensors
Amides
Esters
ferrocene
2-aminopyrimidine

Keywords

  • Crystal structure
  • Heterocycles
  • Homogeneous catalysis
  • Metallocenes

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of ferrocene-labelled 2-aminopyrimidine derivatives via homogeneous catalytic carbonylation. / Fehér, Csaba; Habuš, Ivan; Wouters, Johan; Skoda-Földes, Rita.

In: Monatshefte fur Chemie, Vol. 145, No. 12, 04.09.2014, p. 1981-1986.

Research output: Contribution to journalArticle

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