Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones

A. Csámpai, A. Z. Györfi, Gy I. Túrós, P. Sohár

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A series of ferrocene-containing mono- and bis-dihydropyrimidines (DHP's) were prepared by boric acid mediated three-component Biginelli reactions of formyl- and 1,1′-diformylferrocene, 1,3-dioxo-components and urea. A few further transformations including hydrogenolysis of a benzyl 4-ferrocenyl-DHP-5-carboxylate were also performed. Novel cis-fused saturated pyrimido[4,5-d]pyrimidine-2,7(1H,3H)-diones incorporating [3]-ferrocenophane moiety were constructed by means of iron(III)-catalyzed Biginelli-like condensations of 1,1′-diformylferrocene with urea and in situ generated methyl ketone-derived silyl enol ethers. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements.

Original languageEnglish
Pages (from-to)3667-3673
Number of pages7
JournalJournal of Organometallic Chemistry
Volume694
Issue number22
DOIs
Publication statusPublished - Oct 15 2009

Fingerprint

ureas
Urea
hydrogenolysis
boric acids
Hydrogenolysis
Boric acid
Ethers
Dione
pyrimidines
synthesis
Ketones
ketones
carboxylates
Nuclear magnetic resonance spectroscopy
Condensation
Infrared spectroscopy
ethers
Magnetic Resonance Spectroscopy
Iron
condensation

Keywords

  • [3]-Ferrocenophane
  • Biginelli reaction
  • Dihydropyrimidine
  • Ferrocene
  • NMR spectroscopy

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones. / Csámpai, A.; Györfi, A. Z.; Túrós, Gy I.; Sohár, P.

In: Journal of Organometallic Chemistry, Vol. 694, No. 22, 15.10.2009, p. 3667-3673.

Research output: Contribution to journalArticle

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