A convenient three-component synthesis of substituted cyclopentadienyl tricarbonyl rhenium complexes

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4514-4515

  Minutolo, Filippo ^a   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001400985     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja980433q     Document Type: Letter

References (23)

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2. (b) Hom, R. K.; Katzenellenbogen, J. A. Nucl. Med. Biol. 1997, 24, 485-498.
3. Schwochau, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 2258-2267.
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12. The large size and significant dipole moment associated with most inorganic Re and Tc complexes (generally tetradentate oxo-metal species) can change the properties of the ligand to which they are attached (or are part of) very significantly, thereby interfering with receptor binding affinity and cell membrane permeability. Some of these complexes also have limited stability under physiological conditions (see ref 6). These inconveniences may be avoided with cyclopentadienyl tricarbonyl metal systems.
13. See: Boog, N. M.; Kaesz, H. D. Technetium and Rhenium. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, G. F. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 4, pp 161-242.
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18. Nesmeyanov, A. N.; Kolobova, N. E.; Makarov, Yu. V.; Anisimov, K. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 2, 1992-1996.
19. 3CN (1 mL). If free carboxylic acids were used as the nucleophile, 0.20 mmol of triethylamine was also added. The mixture was heated at 80 °C for 45 min, then concentrated under vacuum. The crude reaction product was purified by flash chromatography. Characterization data and purification conditions of compounds 6b-f are given in the Supporting Information.
20. Nesmeyanov, A. N.; Kolobova, N. E.; Anisimov, K. N.; Makarov, Yu. V. IzV. Akad. Nauk SSSR, Ser. Khim. 1969, 2, 357-359.
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23. 99mTc] pertechnetate; yields comparable to those with perrhenate were obtained. This demonstrates that this reaction works well with technetium at both the macroscopic and tracer level.