The synthesis and reactivity of ferrocenyloxy)-2-tetrahydropyran

https://doi.org/10.1016/S0022-328X(00)85552-7Get rights and content

Abstract

Ferrocenylboronic acid was prepared in good yield via the base hydrolysis of ferrocenylboron dibromide. The ferrocenylboronic acid was converted into hydroxyferrocene which was treated with 2,3-dihydropyran to give (ferrocenyl oxy)-2-tetrahydropyran. Lithiation of this pyran gave the corresponding 2-lithiated ferrocene, which was used to prepare some 1,2-disubstituted ferrocenes including 1-carboxy-2-acetoferrocene (“ferrocenyl-aspirin”).

References (25)

  • R. Epton et al.

    J. Organometal. Chem.

    (1976)
  • A.N. Nesmeyanov et al.

    Tetrahedron Lett.

    (1959)
  • E.I. Edwards et al.

    J. Organometal. Chem.

    (1976)
  • G. Marr

    J. Organometal. Chem.

    (1967)
  • G. Marr et al.

    J. Organometal. Chem.

    (1969)
  • A.N. Nesmeyanov et al.

    Doklady Akad. Nauk SSSR

    (1959)
  • A.N. Nesmeyanov et al.

    Doklady Akad. Nauk SSSR

    (1959)
  • D.W. Slocum et al.

    J. Amer. Chem. Soc.

    (1965)
  • G. Marr et al.

    J. Chem. Soc. C

    (1968)
  • G. Marr et al.

    J. Chem. Soc. C

    (1969)
  • H. Gilman et al.

    Org. Reactions

    (1954)
  • Cited by (41)

    • Aryl ferrocenylmethylesters: Synthesis, solid-state structure and electrochemical investigations

      2020, Arabian Journal of Chemistry
      Citation Excerpt :

      These complexes can be synthesized by the reaction of ferrocene acyl chlorides with alcohols (Huang et al., 2012; Ion, 2001; Moore et al., 1993; Kumara and Menon, 2009; Auzias et al., 2009; Murashima et al., 2005; Khan et al., 2007) or in situ functionalization of 1,1′-bisferrocene dicarboxylic acid with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (Al-Momani and Lataifeh, 2013) or N,N′-dicyclohexylcarbodiimide (Tranchant et al., 2006; Lee et al., 2009), in presence of catalytic amounts of 4-(dimethylamino)pyridine or 1,1′-carbonylbis-1H-imidazole (Hyodo et al., 2002), coordination of two cyclopentadienyl rings, bearing ester function, with iron (Busetto et al., 2001; Busetto et al., 2002; Ou-Yang et al., 2013; Li et al., 2012; Zhao et al., 2011), or oxidation of 1,1′-ferrocene ketones (Yu et al., 2008). Ferrocenyl esters were also accessible from iodoferrocene and carboxylic acids catalyzed by copper(I) compounds (Epton et al., 1977). Moreover, ferrocenyl esters can be prepared by reacting ferrocenylboric acid with aldehydes in the presence of air using N-heterocyclic carbenes as catalysts (Denisov et al., 2015).

    • Ferrocenyl chalcone-based Schiff bases and their metal complexes: Highly efficient, solvent-free synthesis, characterization, biological research

      2018, Journal of Organometallic Chemistry
      Citation Excerpt :

      Organometallics and their metal ion complexes are considered as privileged class of compounds due to their biochemical synthesis, electrochemic-alanalysis, antifungal, antimicrobial as well as catalytic activities [1–6]. As an important part of organometallic compounds, ferrocene and its complexes are used in various fields such as catalysis, material science, crystal engineering and bio-organometallic chemistry [7–10]. It had been reported that the activities of certain drugs were enhanced by introducing ferrocene into their structures such as ferrocene aspirin [11], antimalarial drug ferrocene quine [12], anticancer drug ferrocifen [13], ferrocene-hydr- oxytamox-ifen [14] and ferrchloroquine [15].

    • Synthesis, characterization and antitumor activity of novel ferrocene derivatives containing pyrazolyl-moiety

      2014, Journal of Organometallic Chemistry
      Citation Excerpt :

      In last few years organometallics have got extensive attention owing to their unique chemical structures and biological activities [1,2].

    • Synthesis of novel ferrocene containing vic-dioxime ligands and their Ni(II), Cu(II) and Co(II) complexes: Spectral, electrochemical and biological activity studies

      2011, Journal of Organometallic Chemistry
      Citation Excerpt :

      Like oximes, ferrocene-based ligands have been employed in various fields, such as semiconductors, [9] biosensors, [10] asymmetric catalysis, [11] and nonlinear optics. [12]. The activities of certain drugs are reported to be enhanced by the addition of ferrocene moiety to their structures; e.g., ferrocene aspirin [13], the antimalarial drug ferrocene quinine [14], and anticancer drug ferrocifen [15]. The anticancer potential of ferrocene-containing compounds is also well reported [16–18].

    View all citing articles on Scopus

    Some of these results have been presented in a preliminary form [1].

    View full text