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Synthesis 2007(12): 1768-1778
DOI: 10.1055/s-2007-983705
DOI: 10.1055/s-2007-983705
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Difluoromethylene-Containing 1,2,4-Oxadiazole Compounds via the Reaction of 5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole with Unsaturated Compounds Initiated by Sodium Dithionite
Further Information
Received
28 February 2007
Publication Date:
08 June 2007 (online)
Publication History
Publication Date:
08 June 2007 (online)
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Abstract
5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole, synthesized by the iodination of the corresponding zinc reagent of 5-(bromodifluoromethyl)-3-phenyl-1,2,4-oxadiazole, reacted with various unsaturated compounds, such as alkenes, alkynes, pent-4-en-1-ols, and pent-4-enoic acids, in the presence of sodium dithionite and sodium hydrogen carbonate in aqueous acetonitrile solution at ambient temperature to afford various difluoromethylenated 1,2,4-oxadiazole-containing compounds, including γ-butyrolactones and tetrahydrofurans, in moderate yields.
Key words
difluoromethylene - 1,2,4-oxadiazole - γ-butyrolactone - addition - cyclization
- 1
Reutrakul V.Thongpaisanwong T.Tuchinda P.Kuhakarn C.Pohmakotr M. J. Org. Chem. 2004, 69: 6913 ; and references cited therein - 2
Thaisrivongs A.Pals DT.Kati WM.Turner SR.Thomasco LM. J. Med. Chem. 1985, 28: 1553 - 3
Taguchi T.Mitsunashi A.Yamanouchi A.Kobayashi Y.Sai H.Ikekawa N. Tetrahedron Lett. 1984, 25: 4933 - 4
Hertel LW.Kroin JS.Misner JW.Tustin JM. J. Org. Chem. 1988, 53: 2406 - 5
Buscemi B.Pace A.Piccionello AP.Macaluso G.Vivona N.Spinelli D.Giorgi G. J. Org. Chem. 2005, 70: 3288 ; and references cited therein - 6
Loh VM.Cockcroft XL.Dillon KJ.Dixon L. Bioorg. Med. Chem. Lett. 2005, 15: 2235 - 7
Mylari LB.Banavara L.Beyer TA.Scott PJ.Aldinger CE.Dee MF. J. Med. Chem. 1992, 35: 457 - 8
Santos-Filho JM.Lima JGD.Leite LF. Heterocycl. Commun. 2005, 11: 29 - 9
Howe RK.Schleppnik FM. J. Heterocycl. Chem. 1982, 19: 721 - 10
Chang CS.Lin YT.Shih SR.Lee CC.Lee YC. J. Med. Chem. 2005, 48: 3522 - 11
Tully WR.Gardner CR.Gillespie RJ.Westwood R. J. Med. Chem. 1991, 34: 2060 - 12
Krippner GY.Chalmers DK.Stanislawski PC.Tucker SP.Watson KG. Aust. J. Chem. 2004, 57: 553 - 13
Nicolaides DN.Fylaktakidou KC.Litinas KE.Hadjipavlou-Litina D. Eur. J. Med. Chem. 1998, 33: 715 - 14
Rudewicz P.Pevear DC.Nitz TJ.Aldous SC. J. Med. Chem. 1995, 38: 1355 - 15
Zhu GD.Arendsen DL.Gunawardana IW.Boyd SA.Stewart AO.Fry DG. J. Med. Chem. 2001, 44: 3469 - 16
Buscemi S.Pace A.Pibiri I.Vivona N.Lanza CZ.Spinelli D. Eur. J. Org. Chem. 2004, 5: 974 - 17
Dolbier WR.Burkholder CR.Medebielle M. J. Fluorine Chem. 1999, 95: 127 - 18
Yang XY.Zhu YP.Fang X.Yang XJ.Wu FH.Shen YJ. J. Fluorine Chem. 2007, 128: 174 - 19
Xiao FH.Wu FH.Shen YJ.Zhou LF. J. Fluorine Chem. 2005, 126: 63 - 20
Tiers GVD. J. Org. Chem. 1962, 27: 2261 - 21
Chambers RD.Hutschinson J.Mobbs RH.Musgrave WKR. Tetrahedron 1964, 20: 497 -
22a
Brace NO. J. Org. Chem. 1973, 38: 3167 -
22b
Rong GB.Keese R. Tetrahedron Lett. 1990, 31: 5615 -
23a
Chen QY.Qiu ZM.Yang ZY. J. Fluorine Chem. 1987, 36: 149 -
23b
Qiu WM.Burton DJ. J. Org. Chem. 1993, 58: 419 -
23c
Kotora M.Hajek M.Ameduri B.Boutevin B. J. Fluorine Chem. 1994, 68: 49 -
23d
Chen J.Hu CM. J. Chem. Soc., Perkin Trans. 1 1994, 1111 - 24
Guo XC.Chen QY. J. Fluorine Chem. 1998, 88: 63 - 25
Huang BN.Wu FH.Zhou CM. J. Fluorine Chem. 1995, 95: 1 - 26
Brace NO. J. Org. Chem. 1972, 37: 2429 - 27
Brace NO. J. Org. Chem. 1963, 28: 3093 - 28
Li AR.Chen QY. Synthesis 1997, 333 - 29
Huang WY.Lv L.Zhang YF. Chin. J. Chem. 1990, 350 - 30
Kobayashi T.Eda T.Tamura O.Ishibashi H. J. Org. Chem. 2002, 67: 3156 -
31a
Liu SQ.Wang SW.Qing FL. J. Fluorine Chem. 2005, 126: 771 -
31b
Ghattas W.Hess CR.Lacazio G.G ardre R. J. Org. Chem. 2006, 71: 8618 - 32
Hartung J.Kneuer R.Laug S.Schmidt P. Eur. J. Org. Chem. 2003, 20: 4033 - 33
Roussi R.Bellia F. Tetrahedron Lett. 1998, 39: 3017 - 34
Sugimoto T.Kaiser ET. J. Am. Chem. Soc. 1979, 101: 3046 - 35
Yang ZY.Burton DJ. J. Org. Chem. 1991, 56: 5125 - 36
Zou XW.Wu FH.Shen YJ.Xu S.Huang WY. Tetrahedron 2003, 59: 2555