Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 10
709
Views
15
CrossRef citations to date
0
Altmetric
Original Articles

o-Iodoxy Benzoic Acid–Mediated Synthesis of 3,5-Diarylisoxazoles and Isoxazole-3-carboxylic Acids

, &
Pages 1453-1460 | Received 26 Aug 2013, Published online: 29 Apr 2014

REFERENCES

  • Thottumkar , A. P. ; Thottumkar , K. V. Synthesis and oxidation of user- and ecofriendly hypervalent iodine reagent . Tetrahedron Lett. 2002 , 43 , 569 – 572 .
  • Das , B. ; Holla , H. ; Mahender , G. ; Banerjee , J. ; Reddy , M. R. Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: A new and efficient method for the preparation of nitrile oxides from aldoximes. Tetrahedron Lett. 2004, 45, 7347–7350.
  • Du , L.-H. ; Wang , Y.-G. A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant . Synthesis 2007 , 675 – 678 .
  • Wirth , T. ; Hirt , U. H. Hypervalent iodine compounds: Recent advances in synthetic application . Synthesis 1999 , 1271 – 1287 .
  • More , J. D. ; Finney , N. A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX) . Org. Lett. 2002 , 4 ( 17 ), 3001–3003.
  • Nicolaou , K. C. ; Baran , P. S. ; Zhong , Y.-L. Selective oxidation at carbon adjacent to aromatic systems with IBX . J. Am. Chem. Soc. 2001 , 123 , 3183 – 3185 .
  • Nicolaou , K. C. ; Mathison , C. J. N. ; Montagnon , T. o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen and sulphur containing substrates, scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections . J. Am. Chem. Soc. 2004 , 126 , 5192 – 5201 .
  • Barco , A. ; Benitti , S. ; Pollini , G. P. ; Simoni , D. Synthesis of natural products via isoxazoles . Synthesis 1987 , 857 – 869 .
  • Kondo , Y. ; Uchiyama , D. ; Sakamoto , T. ; Yamanaka , H. Synthesis and reactions of 5-(tributylstannyl)isoxazoles . Tetrahedron Lett. 1989 , 30 , 4249 – 4250 .
  • Morriyo , O. ; Nakamura , H. ; Kageyama , T. ; Urata , Y. Synthesis of isoxazolines and isoxazoles from aldoximes by the use of sodium bromite with organotin halide . Tetrahedron Lett. 1989 , 30 , 3987 – 3990 .
  • Dominguez , E. ; Ibeus , E. ; Martinez de Margart , E. ; Palacius , J. K. ; San Marka , E. A convenient one-pot preparative method for 4,5-diarylisoxazole involving exchange reactions . J. Org. Chem. 1996 , 61 , 5435 – 5439 .
  • Talley , J. J. ; Brown , D. L. ; Carter , J. S. ; Graneto , M. J. ; Koboldt , C. M. ; Zweifel , B. S. ; Seibert , K. ; Masferrer , J. L. ; Perkins , W. E. ; Rogers , R. S. ; Shaffer , A. F. ; Zhang , Y. Y. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, Valdecoxib: A potent and selective inhibitor of COX-2 . J. Med. Chem. 2000 , 43 , 775 – 777 .
  • Lee , Y.-S. ; Kim , B. H. Heterocyclic nucleoside analogues: Design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles . Bioorg. Med. Chem. Lett. 2002 , 12 , 1395 – 1397 .
  • Desai , V. G. ; Tilve , S. G. A novel and convenient method towards synthesis of 3,5-diarylisoxazoles . Synth. Commun. 1999 , 29 ( 17 ), 3017 – 3020 .
  • Kurangi , R. F. ; Kawthankar , R. ; Sawal , S. ; Desai , V. G. ; Tilve , S. G. A convenient synthesis of 3,5-disubstituted isoxazoles . Synth. Commun. 2007 , 37 , 585 – 587 .
  • Buchi , G. ; Vedera , J. C. Interchange of functionality in conjugated carbonyl compounds through isoxazoles . J. Am. Chem. Soc. 1972 , 94 , 9128 – 9132 .
  • Wei , X. ; Fang , J. ; Hu , Y. ; Hu , H. A convenient preparation of 3,5-diarylisoxazoles . Synthesis 1992 , 1205 – 1206 .
  • Balasundaram , B. ; Perumal , P. T. A new method for the synthesis of substituted 3,5-diphenylisoxazoles . Synth. Commun. 1990 , 20 , 293 – 299 .
  • Hansen , J. F. ; Strong , S. A. Reaction of vinyl ketoximes with N-bromosuccinimide: Synthesis of isoxazoles and 4-bromoisoxazolines . J. Heterocycl. Chem. 1977 , 14 , 1289 – 1292 .
  • Ichinose , N. ; Mizuno , K. ; Tamai , T. ; Otsuji , Y. A novel NO insertion into cyclopropane ring by use of NOBF4 formation of 2-isoxazolines . Chem. Lett. 1988 , 233 – 236 .
  • Fulmer , T. D. ; Dasher , L. P. ; Bobb , B. L. ; Wilson , J. D. ; Sides , K. L. ; Beam C. F. An improved synthesis of 3,5-disubstitutedisoxazoles and pyrazoles from C(α)o-dithiooximes and C (α), N-dithiophenylhydrazones . J. Heterocycl. Chem. 1980 , 17 ( 4 ), 799 – 800 .
  • Kidwai , M. ; Kukreja , S. ; Thakur , R. K2CO3-mediated regioselective synthesis of isoxazoles and pyrazolines. Lett. Org. Chem. 2006, 3, 135–139.
  • Balalaie , S. ; Sharifi , A. ; Ahangarian , B. Solid-phase synthesis of isoxazoles and pyrazoles under microwave irradiations . Ind. J. Heterocycl. Chem. 2000 , 10 , 149 – 150 .
  • Shi , X.-N. ; Wang , J.-X. Microwave irradiation synthesis of 3,5-diarylisoxazoles in aqueous solutions . Yingyong Huaxue. 2010 , 27 ( 5 ), 539 – 543 .
  • Molteni , V. ; Hamilton , M. M. ; Long , M. ; Crane , C. M. ; Termin , A. P. ; Wilson , D. M. Aqueous one-pot synthesis of pyrazoles, pyrimidines, and isoxazoles promoted by microwave irradiation . Synthesis 2002 , 1669 – 1674 .
  • Hansen , T. V. ; Wu , P. ; Fokin , V. V. One-pot copper(I)-catalysed synthesis of 3,5-disubstituted isoxazoles . J. Org. Chem. 2005 , 70 ( 19 ), 7761 – 7764 .
  • Tang , S. ; He , J. ; Sun , Y. ; She , X. Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles . Org. Lett. 2009 , 11 ( 17 ), 3982 – 3985 .
  • Beam , C. F. ; Dyer , M. C. D. ; Schwarz , R. A. ; Hauser , C. R. New synthesis of isoxazoles from 1,4-dianions of oximes having an α-hydrogen: Mass spectrometry . J. Org. Chem. 1970 , 35 ( 6 ), 1806 – 1810 .
  • Benjamin , W. ; Rominger , F. ; Muller , T. J. J. Novel microwave-assisted one-pot synthesis of isoxazoles by a three-component coupling–cycloaddition sequence . Synthesis 2008 , 293 – 303 .
  • Mao , J. ; Yuan , H. ; Wang , Y. ; Wan , B. ; Pak , D. ; He , R. ; Franzblan , S. G. Synthesis and tuberculosis activity of novel mefloquine isoxazole carboxylic ester as prodrugs . Bioorg. Med. Chem. Lett. 2010 , 20 ( 3 ), 1263 – 1268 .
  • Rover , S. ; Cesura , M. A. ; Huguenin , P. ; Kettler , R. ; Szente , A. Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high affinity inhibitor of kynurenine-3-hydroxylase . J. Med. Chem. 1997 , 40 , 4378 – 4385 .
  • Zhao , H. ; Liu , G. ; Xin , Z. ; Serby , M. D. ; Pei , Z. ; Szczepankiewicz , B. G. ; Hajduk , P. J. ; Ballaron , S. J. ; Haasch , D. L. Isoxazole carboxylic acids as protein tyrosine phosphatise 1B (PTP1B) inhibitors . Bioorg. Med. Chem. Lett. 2004 , 14 ( 22 ), 5543 – 5546 .
  • Wang , S. ; Yan , J. ; Chen , J. Zhang , T. ; Zhao , Y. ; Xue , M. Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors . Eur. J. Med. Chem. 2010 , 45 ( 6 ), 2663 – 2670 .
  • Becht , J.-M. ; Maruani , M. ; Wagner , A. ; Mioskonski , C. Short and efficient preparations of isoxazole-3-carboxylic acid and imino-oxopentanoic acid potent precursors of 4-hydroxyisoleucine . Tetrahedron 2006 , 62 ( 18 ), 4430 – 4434 .
  • Grundmann , C. Nitrile oxides VIII: Cyanogen N-oxide . J. Org. Chem. 1966 , 31 ( 12 ), 4235 – 4237 .
  • Shotter , R. G. ; Seshadri , D. ; Wright , P. H. α,β-Unsaturated oximes: Isoxazoline formation by thermal cyclisation of compounds related to benzalacetophenone oxime and isoxazoline thermal cycloreversion reactions . Tetrahedron 1975 , 31 , 3069 – 3072 .
  • Babar , L. Synthesis and fungicity of 3,5-disubstituted isoxazoles . Pesticide Res. J. 2005 , 17 ( 2 ), 1 – 5 .
  • Sharma , P. ; Kaur , N. ; Pareek , A. ; Kishore , D. An insight into general features of IBX (2-iodoxy benzoic acid) . Sci. Rev. Chem. Commun. 2013 , 3 ( 1 ), 16 – 42 .
  • Nicolaou , K. C. ; Montagnon , T. ; Baran , P. S. ; Zhong , Y.-L. Iodine(V) reagents in organic synthesis, part 4: o-Iodoxybenzoic acid as a chemospecific tool for single-electron-transfer-based oxidation processes . J. Am. Chem. Soc. 2002 , 124 ( 10 ), 2245 – 2258 .
  • Frigerio , M. ; Santagostina , M. ; Sputore , S. A user-friendly entry to 2-iodoxybenzoic acid (IBX) . J. Org. Chem. 1999 , 64 ( 12 ), 4537 – 4538 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.