Abstract
Four new fluorinated aldehydes (5-Rf S-2-furfuraldehyde; Rf = 4-CF3 C6 F4 for 1 , 4-C6 HF4 for 2 , 4-CF3 C6 H4 for 3 and 2,4-C6 H3 F2 for 4 ) derived from 5-bromo-2-furfuraldehyde have been prepared. Treatment of compounds 1 -4 with thiosemicarbazide afford the corresponding 5-Rf S-2-furfuraldehyde thiosemicarbazones (Rf = 4-CF3 C6 F4 for 5 , 4-C6 HF4 for 6 , 4-CF3 C6 H4 for 7 and 2,4-C6 H3 F2 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
7 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 data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
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