Synthesis of the New 5-(Fluorobenzenethiolated)-2-furfuraldehyde Thiosemicarbazones

Abstract

Four new fluorinated aldehydes (5-R_fS-2-furfuraldehyde; R_f = 4-CF₃C₆F₄ for 1, 4-C₆HF₄ for 2, 4-CF₃C₆H₄ for 3 and 2,4-C₆H₃F₂ for 4) derived from 5-bromo-2-furfuraldehyde have been prepared. Treatment of compounds 1-4 with thiosemicarbazide afford the corresponding 5-R_fS-2-furfuraldehyde thiosemicarbazones (R_f = 4-CF₃C₆F₄ for 5, 4-C₆HF₄ for 6, 4-CF₃C₆H₄ for 7 and 2,4-C₆H₃F₂ for 8). The molecular structure of compound 6 has been determined.

Key words

fluorine - furans - sulfur - thiosemicarbazones - furfuraldehyde

References

• 1a Babb JEV. Burrows AD. Harrington RW. Mahon MF. Polyhedron  2003,  22:  673 
• 1b Burrows AD. Menzer S. Mingos DMP. White AJP. Williams DJ. J. Chem. Soc., Dalton Trans.  1997,  4237 ; and references therein
• 2a Ren P. Liu T. Qin J. Chen C. Spectrochim. Acta, Part A  2003,  59:  1095 
• 2b Tian Y. Yu W. Zhao C. Jiang M. Cai Z. Fun HK. Polyhedron  2002,  21:  1217 
• 2c Tian Y. Duan C. Zhao C. You X. Mak TCW. Zhang Z. Inorg. Chem.  1997,  36:  1247 
• 3a Philip V. Suni V. Kurup MRP. Nethaji M. Polyhedron  2004,  23:  1225 
• 3b Quiroga AG. Ranninger CN. Coord. Chem. Rev.  2004,  248:  119 
• 3c Chen J. Huang Y. Liu G. Afrasiabi Z. Sin E. Padhye S. Ma Y. Tox. Appl. Pharm.  2004,  197:  40 
• 3d Ferrari MB. Bisceglie F. Pelosi G. Tarasconi P. Albertini R. Dall’Aglio PP. Pinelli S. Bergamo A. Sava G. J. Inorg. Biochem.  2004,  98:  301 
• 3e Baldini M. Ferrari MB. Bisceglie F. Pelosi G. Pinelli S. Tarasconi P. Inorg. Chem.  2003,  42:  2049 
• 4a Yoshida S. Meyer OGJ. Rosen TC. Haufe G. Ye S. Sloan MJ. Kirk KL. J. Med. Chem.  2004,  47:  1796 
• 4b Zheng X. Li Z. Wang Y. Chen W. Huang Q. Liu C. Song G. J. Fluorine Chem.  2003,  123:  163 
• 4c Kline T. Andersen NH. Harwood EA. Bowman J. Malanda A. Endsley S. Erwin AL. Doyle M. Fong S. Harris AL. Mendelsohn B. Mdluli K. Raetz CRH. Stover CK. Witte PR. Yabannavar A. Zhu S. J. Med. Chem.  2002,  45:  3112 
• 4d Nakazato A. Kumagai T. Sakagami K. Yoshikawa R. Suzuki Y. Chaki S. Ito H. Taguchi T. Nakanishi S. Okuyama S. J. Med. Chem.  2000,  43:  4893 
• 5a Kurup MRP. Joseph M. Synth. React. Inorg. Metal-Org. Chem.  2003,  33:  1275 
• 5b Jouad EM. Larcher G. Allain M. Riou A. Bouet GM. Khan MA. Thanh XD. J. Inorg. Biochem.  2001,  86:  565 
• 5c Ibrahim G. Chebli E. Khan MA. Bouet GM. Trans. Met. Chem.  1999,  24:  294 
• 6a Wang Q. Mao Y. Hu C. J. Fluorine Chem.  1999,  94:  79 
• 6b Ferrari MB. Capacchi S. Bisceglie F. Pelosi G. Tarasconi P. Inorg. Chim. Acta  2001,  312:  81 
• 8a Alonso R. Bermejo E. Carballo R. Castiñeiras A. Pérez T. J. Mol. Struct.  2002,  606:  155 
• 8b Casas JS. García-Tasende MS. Sordo J. Coord. Chem. Rev.  2000,  209:  197 
• 9 Jouad EM. Allain M. Khan MA. Bouet GM. J. Mol. Struct.  2002,  604:  205 
• 10 Sundararaman A. Lalancette RA. Zakharov LN. Rheingold AL. Jäkle F. Organometallics  2003,  22:  3526 
• 11a Martin E. Tovilla J. Torrens H. Synthesis  2000,  1109 
• 11b Kurup MRP. Joseph M. Synth. React. Inorg. Metal-Org. Chem.  2003,  33:  1275 
• 12a Jouad EM. Allain M. Khan MA. Bouet GM. J. Mol. Struct.  2002,  604:  205 
• 12b Vàzquez-García D. Fernández A. Fernández JJ. López-Torres M. Suárez A. Ortigueira JM. Vila JM. Adams H. J. Organomet. Chem.  2000,  595:  199 

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CCDC 247008 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing [e-mail], or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone].