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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 24
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Original Articles

Synthesis of Thiazoles and Aminothiazoles from β‐Keto Tosylates under Supramolecular Catalysis in the Presence of β‐Cyclodextrin in WaterFootnote

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Pages 4331-4336 | Received 09 May 2007, Published online: 14 Dec 2007

References

  • Benazzouz , A. , Boraud , T. , Dubedat , P. , Boireau , A. , Stutzmann , J.-M. and Gross , C. 1995 . Riluzole prevents MPTP-induced parkinsonism in the rhesus monkey: a pilot study . Eur. J. Pharmacol , 284 : 299
  • Jimonet , P. , Audiau , F. , Barreau , M. , Blanchard , J.-C. , Boireau , A. , Bour , Y. , Coleno , M.-A. , Doble , A. , Doerflinger , G. , Huu , C. D. , Donat , M.-H. , Duchesne , J. M. , Ganil , P. , Gueremy , C. , Honore , E. , Just , B. , Kerphirique , R. , Gontier , S. , Hubert , P. , Laduron , P. M. , Blevec , J. L. , Meunier , M. , Miquet , J.-M. , Nemecek , C. , Pasquet , M. , Piot , O. , Pratt , J. , Rataud , J. , Reibaud , M. , Stutzmann , J.-M. and Mignani , S. 1999 . Riluzole series. Synthesis and in vivo “Antiglutamate”, activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines benzothiazolines as antituberculous agents . J. Med. Chem. , 42 : 2828
  • Palmer , P. J. , Trigg , R. B. and Warrington , J. V. 1971 . Benzothiazolines as antituberculous agents . J. Med. Chem. , 14 : 248
  • Patt , W. C. , Hamilton , H. W. , Taylor , M. D. , Ryan , M. J. , Taylor , D. G. Jr. , Connolly , C. J. C. , Doharty , A. M. , Klutchko , S. R. , Sircar , I. , Steinbaugh , B. A. , Bately , B. L. , Painchand , C. A. , Rapundalo , S. T. , Michniewicz , B. M. and Olzon , S. C. J. 1992 . Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors . J. Med. Chem. , 35 : 2562
  • Haviv , F. , Ratajczyk , J. D. , DeNet , R. W. , Kerdesky , F. A. , Walters , R. L. , Schmidt , S. P. , Holms , J. H. , Young , P. R. and Carter , G. W. 1988 . 3-[1-(2-Benzoxazolyl)hydrazino] propane nitrile derivatives: inhibitors of immune complex induced inflammation . J. Med. Chem. , 31 : 1719
  • Clemence , F. , Marter , O. L. , Delevalle , F. , Benzoni , J. , Jouanen , A. , Jouquey , S. , Mouren , M. and Deraedt , R. 1988 . 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities . J. Med. Chem , 31 : 1453
  • Ivanov , S. K. and Yuritsyn , V. S. 1971 . Inhibiting action of organic sulfur compounds during cumin oxidation . Neftekhimiya , 11 : 99 Chem. Abstr. 1971, 74, 124487 m
  • Mylari , B. L. , Larson , R. , Beyer , T. A. , Zembrowski , W. J. , Aldinger , C. E. , Dee , M. F. , Siegel , T. W. and Singleton , D. H. 1991 . Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1-phthalazineacetic acid (zopolrestat) and congeners . J. Med. Chem , 34 : 108
  • Kotani , T. , Nagaki , Y. , Ishii , A. , Konishi , Y. , Yago , H. , Suehiro , S. , Okukado , N. and Okamoto , K. 1997 . Highly selective Aldose reductase inhibitors. 3. Structural diversity of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids . J. Med. Chem. , 40 : 684
  • Hadjipavlou-Litina , D. J. and Geronikaki , A. A. 1998 . Thiazolyl and benzothiazolyl Schiff bases as novel possible lipoxygenase inhibitors and anti inflammatory agents. Synthesis and biological evaluation . Drug Des. Discovery , 15 : 199
  • Oketani , K. , Inoue , T. and Murakami , M. 2001 . Effect of E3040, an inhibitor of 5-lipoxygenase and thromboxane synthase, on rat bowel damage induced by lipopolysaccharide . Eur. J. Pharmacol. , 427 : 159
  • Nagel , A. A. , Liston , D. R. , Jung , S. , Mahar , M. , Vincent , L. A. , Chapin , D. , Chen , Y. L. , Hubbard , S. , Ives , J. L. and Jones , S. B. 1995 . Design and synthesis of 1-heteroaryl-3-(1-benzyl-4-piperidinyl)propan-1-one derivatives as potent, selective acetylcholinesterase inhibitors . J. Med. Chem , 38 : 1084
  • Sohn , S. K. , Chang , M. S. , Choi , W. S. , Kim , K. W. , Woo , T. W. , Lee , S. B. and Chung , Y. K. 1999 . Biochemical and pharmacological characteristics of a newly synthesized H+-K+ ATPase inhibitor, YJA20379-1,2-amino-4,5-dihydro-8-phenylimidazole[2,1-b]thiazolo[5,4-g]benzothiazole . Can. J. Physiol. Pharmacol. , 77 : 330
  • Phoon , C. W. , Ng , P. Y. , Ting , A. E. , Yeo , S. L. and Sim , M. M. 2001 . Biological evaluation of hepatitis c virus helicase inhibitors . Bioorg. Med. Chem. Lett. , 11 : 1647
  • Baxter , A. D. 1997 . Synthesis utilizing insoluble polymers: new reactions and small molecules . Curr. Opin. Chem. Biol. , 1 : 79
  • Rich , D. H. and Wiley , R. A. 1993 . Peptidomimetics derived from natural products . Med. Res. Rev. , 13 : 327
  • Kearney , P. C. , Fernandez , M. and Flygare , J. A. 1998 . Solid-phase synthesis of 2-aminothiazoles . J. Org. Chem. , 63 : 196
  • Goff , D. and Fernandez , J. 1999 . The preparation of 2,4-disubstituted thiazoles on solid support . Tetrahedron Lett. , 40 : 423
  • Surendra , K. , Krishnaveni , N. S. and Rao , K. R. 2005 . Study of the Michael addition of β-cyclodextrin–thiol complexes to conjugated alkenes in water . Chem. Commun. , : 669
  • Krishnaveni , N. S. , Surendra , K. and Rao , K. R. 2004 . A simple and highly selective biomimetic oxidation of alcohols and epoxides with N-bromosuccinimide in the presence of β-cyclodextrin in water . Adv. Synth. Catal. , 346 : 346
  • Surendra , K. , Krishnaveni , N. S. , Reddy , M. A. , Nageswar , Y. V. D. and Rao , K. R. 2003 . Highly selective oxidative cleavage of ββ-cyclodextrin-epoxide//aziridine complexes with IBX in water . J. Org. Chem. , 68 : 9119
  • Surendra , K. , Krishnaveni , N. S. , Nageswar , Y. V. D. and Rao , K. R. 2003 . Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water . J. Org. Chem. , 68 : 4994
  • Surendra , K. , Krishnaveni , N. S. , Reddy , M. A. , Nageswar , Y. V. D. and Rao , K. R. 2003 . Mild oxidation of alcohols with o-Iodoxybenzoic Acid (IBX) in water/acetone mixture in the presence of β-cyclodextrin . J. Org. Chem. , 68 : 2058
  • Schneider , H. J. , Hacket , F. , Rudiger , V. and Ikeda , H. 1998 . NMR studies of cyclodextrins and cyclodextrin complexes . Chem. Rev. , 98 : 1755
  • Demarco , P. V. and Thakkar , A. L. 1970 . Cyclohepta-amylose inclusion complexes. A proton magnetic resonance study . J. Chem. Soc. Chem. Commun. , : 2
  • Ukema , K. , Hirayama , F. and Irie , T. 1998 . Cyclodextrin drug carrier systems . Chem. Rev. , 98 : 2045
  • Szejtli , J. 1991 . Comprehensive Supramolecular Chemistry Edited by: Szejtli , J. and Osa , T. Vol. 3 , 5 Oxford : Pergamon .

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