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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 22
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Original Articles

Polymer-Supported Vinyl Sulfone as an Efficient Reagent for the Synthesis of 3-Monosubstituted Isoxazoles

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Pages 3034-3043 | Received 05 Oct 2012, Published online: 08 Aug 2013

REFERENCES

  • (a) Ziegert , R. E. ; Torang , J. ; Knepper , K. ; Brase , S. The recent impact of solid-phase synthesis on medicinally relevant benzoannelated oxygen heterocycles . J. Comb. Chem. 2005 , 7 , 147 – 169 ; (b) Feliu , L. ; Vera-Luque , P. ; Albericio , F. ; Alvarez , M. Solid-phase synthesis of biologically active benzoannelated nitrogen heterocycles: An update . J. Comb. Chem. 2009 , 11 , 175 – 197 .
  • (a) Döwald , F. Z. Organic Synthesis on Solid Phase: Supports, Linkers, Reactions, , 2nd ed. ; Wiley-VCH : Weinehim , 2002 ; (b) Scott , P. Linker Strategies in Solid-Phase Organic Synthesis ; Wiley-VHC : Weinheim , 2009 .
  • (a) Franzen , R. G. Recent advances in the preparation of heterocycles on solid support: A review of the literature . J. Comb. Chem. 2000 , 2 , 195 – 214 ; (b) Krchnak , V. ; Holladay , M. W. Solid-phase heterocyclic chemistry . Chem. Rev. 2002 , 102 , 61 – 92 ; (c) Blaney , P. ; Grigg , R. ; Sridharan , V. Traceless solid-phase organic synthesis . Chem. Rev. 2002 , 102 , 2607 – 2624 .
  • (a) Talley , J. J. ; Brown , D. L. ; Carter , J. S. ; Graneto , M. J. ; Koboldt , C. M. ; Masferrer , J. L. ; Perkins , W. E. ; Rogers , R. S. ; Shaffer , A. F. ; Zhang , Y. Y. ; Zweifel , B. S. ; Seibert , K. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: A potent and selective inhibitor of COX-2 . J. Med. Chem. 2000 , 43 , 775 – 777 ; (b) 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 ; (c) Srivastava , S. ; Bajpai , L. K. ; Batra , S. ; Bhaduri , A. P. ; Maikhuri , J. P. ; Gupta , G. ; Dhar , J. D. In search of new chemical entities with spermicidal and anti-HIV activities . Bioorg. Med. Chem. 1999 , 7 , 2607 – 2613 ; (d) Simoni , D. ; Grisolia , G. ; Giannini , G. ; Roberti , M. ; Rondanin , R. ; Piccagli , L. ; Baruchello , R. ; Rossi , M. ; Romagnoli , R. ; Invidiata , F. P. ; Grimaudo , S. ; Jung , M. K. ; Hamel , E. ; Gebbia , N. ; Crosta , L. ; Abbadessa , V. ; Di Cristina , A. ; Dusonchet , L. ; Meli , M. ; Tolomeo , M. Heterocyclic and phenyl double-bond-locked combretastatin analogues possessing potent apoptosis-inducing activity in HL60 and in MDR cell lines . J. Med. Chem. 2005 , 48 , 723 – 736 ; (e) Kaffy , J. ; Pontikis , R. ; Carrez , D. ; Croisy , A. ; Monneret , C. ; Florent , J. C. Isoxazole-type derivatives related to combretastatin A-4, synthesis, and biological evaluation . Bioorg. Med. Chem. 2006 , 14 , 4067 – 4077 .
  • For recent reviews, see (a) Wakefield , B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations ; E. Shaumann , (Ed.); Georg Thieme Verlag : Stuttgart , 2001 ; vol. 11 , pp. 229 – 288 ; (b) Jäger , V. ; Colinas , P. A. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products ; A. Padwa , (Ed.); Wiley : Hoboken , NJ , 2002 ; vol. 59 , pp. 361 – 472 ; (c) Pinho e Melo , T. M. V. D. Recent advances on the synthesis and reactivity of isoxazoles. Curr. Org. Chem. 2005, 9, 925–958; (d) Stanley , L. M. ; Sibi , M. P. Enantioselective copper-catalyzed 1,3-dipolar cycloadditions. Chem. Rev. 2008, 108, 2887–2902.
  • For recent studies on the synthesis of disubstituted isoxazoles, see (a) Debleds , O. ; Gayon , E. ; Ostaszuk , E. ; Vrancken , E. ; Campagne , J.-M. A versatile iron-catalyzed protocol for the one-pot synthesis of isoxazoles or isoxazolines from the same propargylic alcohols. Chem. Eur. J. 2010, 16, 12207–12213; (b) Tang , S. ; He , J. ; Sun , Y. ; He , L. ; She , X. Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols. J. Org. Chem. 2010, 75, 1961–1966; (c) Conti , P. ; Pinto , A. ; Tamborini , L. ; Dunkel , P. ; Gambaro , V. ; Viscoti , G. L. ; Micheli , C. D. A regioselective route to 5-substituted isoxazole- and isoxazoline-3-phos-phonates. Synthesis 2009, 591–596; (d) Bhosale , S. ; Kurhade , S. ; Prasad , U. V. ; Palle , V. P. ; Bhuniya , D. Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve™ (CrO2). Tetrahedron Lett. 2009, 50, 3948–3951; (e) McClendon , E. ; Omollo , A. O. ; Valente , E. J. ; Hamme II , A. T. , Oxonium ion–mediated synthesis of 4-substituted spiro-isoxazolines. Tetrahedron Lett. 2009, 50, 533–535; (f) Grecian , S. ; Fokin , V. V. Ruthenium-catalyzed cycloaddition of nitrile oxides and alkynes: Practical synthesis of isoxazoles. Angew. Chem., Int. Ed. 2008, 47, 8285–8287; (g) Willy , B. ; 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; (h) Girardin , M. ; Alsabeh , P. G. ; Lauzon , S. ; Dolman , S. J. ; Ouellet , S. G. ; Hughes , G. Synthesis of 3-aminoisoxazoles via the addition–elimination of amines on 3-bromoisoxazolines. Org. Lett. 2009, 11, 1159–1162; (i) Ueda , M. ; Ikeda , Y. ; Sato , A. ; Ito , Y. ; Kakiuchi , M. ; Shono , H. ; Miyoshi , T. ; Naito , T. ; Miyata , O. Silver-catalyzed synthesis of disubstituted isoxazoles by cyclization of alkynyl oxime ethers. Tetrahedron 2011, 67, 4612–4615; (j) Murarka , S. ; Studer , A. Zinc triflate–catalyzed aerobic cross-dehydrogenative coupling (CDC) of alkynes with nitrones: A new entry to isoxazoles. Org. Lett. 2011, 13, 2746–2749; (k) Itoh , K.-I. ; Aoyama , T. ; Satoh , H. ; Fujii , Y. ; Sakamaki , H. ; Takido , T. ; Kodomari , M. Application of silica gel–supported polyphosphoric acid (PPA/SiO2) as a reusable solid acid catalyst to the synthesis of 3-benzoylisoxazoles and isoxazolines. Tetrahedron Lett. 2011, 52, 6892–6895; (l) Dissanayake , A. A. ; Odom , A. L. Regioselective conversion of alkynes to 4-substituted and 3,4-disubstituted isoxazoles using titanium-catalyzed multicomponent coupling reactions. Tetrahedron 2012, 68, 807–812; (m) Tang , N. ; Sheng , S.-R. ; Hu , Q.-S. ; Qu , H.-E. ; Cai , M.-Z. Solid-phase synthesis of isoxazole-5-carboxylates based on Wang resin-bound 1-phenylselenoacrylate. Synth. Commun. 2012, 42, 3279–3287.
  • For recent studies on the synthesis of trisubstituted isoxazoles, see (a) Denmark , S. E. ; Kallemeyn , J. M. Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions . J. Org. Chem. 2005 , 70 , 2839 – 2842 ; (b) Moore , J. E. ; Davies , M. W. ; Goodenough , K. M. ; Wybrow , R. A. ; York , M. ; Johnson , C. N. ; Harrity , J. P. A. Investigation of the scope of a [3 + 2] cycloaddition approach to isoxazole boronic esters . Tetrahedron 2005 , 61 , 6707 – 6714 ; (c) Bourbeau , M. P. ; Rider , J. T. A convenient synthesis of 4-alkyl-5-aminoisoxazoles . Org. Lett. 2006 , 8 , 3679 – 3680 ; (d) Waldo , J. P. ; Mehta , S. ; Neuenswander , B. ; Lushington , G. H. ; Larock , R. C. Solution-phase synthesis of a diverse library of highly substituted isoxazoles . J. Comb. Chem. 2008 , 10 , 658 – 663 ; (e) Minakata , S. ; Okumura , S. ; Nagamachi , T. ; Takeda , Y. Generation of nitrile oxides from oximes using t-BuOI and their cycloaddition . Org. Lett. 2011 , 13 , 2966 – 2969 ; (f) Okitsu , T. ; Sato , K. ; Potewar , T. M. ; Wada , A. Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles . J. Org. Chem. 2011 , 76 , 3438 – 3449 ; (g) Chappell , B. ; Dedman , N. ; Wheeler , S. Studies on the palladium-catalysed direct alkenylation of 1,2-azoles . Tetrahedron Lett. 2011 , 52 , 3223 – 3225 ; (h) Rajender , P. S. ; Sridevi , G. ; Reddy , K. K. Synthesis of novel isoxazole fused heterocycles . Synth. Commun. 2012 , 42 , 2191 – 2200 .
  • (a) Shvekhgeimer , G. A. ; Baranski , A. ; Grzegozek , M. Reaction of benzonitrile oxides with conjugated nitroalkenes . Synthesis 1976 , 612 – 614 ; (b) Barber , G. N. ; Olofson , R. A. A useful, regiospecific synthesis of isoxazoles . J. Org. Chem. 1978 , 43 , 3015 – 3021 ; (c) Padwa , A. ; MacDonald , J. G. Utilization of vinylsilanes in [4 + 2]-cycloaddition reactions . J. Org. Chem. 1983 , 48 , 3189 – 3195 ; (d) Di Nunno , L. ; Scilimati , A. Synthesis of 3-aryl-4, 5-dihydro-5-hydroxy-1,2-oxazoles by reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde . Tetrahedron 1987 , 43 , 2181 – 2189 .
  • For recent studies on the synthesis of 3-monosubstituted isoxazoles, see (a) Sheng , S. R. ; Liu , X. L. ; Xu , Q. ; Song , C. S. One-pot synthesis of 3-substituted isoxazoles from phenyl vinylic selenide. Synthesis 2003, 2763–2764; (b) Cermola , F. ; Di Gioia , L. ; Graziano , M. L. ; Iesce , M. R. Ring-opening reactions of cyclopropanes, part 8.1: Nitrosation of donor–acceptor cyclopropanes. J. Chem. Res. 2005, 677–681; (c) Sheng , S.-R. ; Xin , Q. ; Liu , X.-L. ; Sun , W.-K. ; Guo , R. ; Huang , X. Traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines using polystyrene-supported vinyl selenide. Synthesis 2006, 2293–2296; (d) Di Nunno , L. ; Vitale , P. ; Scilimati , A. Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.0 2,5]octan-4,8-diones induced by LDA. Tetrahedron 2008, 64, 11198–11204; (e) Rosa , F. A. ; Machado , P. ; Bonacorso , H. G. ; Zanatta , N. ; Martins , M. A. P. Reaction of β-dimethylaminovinyl ketones with hydroxylamine: A simple and useful method for synthesis of 3- and 5-substituted isoxazoles. J. Heterocycl. Chem. 2008, 45, 879–885; (f) Tang , S. ; He , J. ; Sun , Y. ; He , L. ; She , X. Efficient and regiospecific one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles. Org. Lett. 2009, 11, 3982–3985.
  • Simpkins , N. S. Sulphones in Organic Synthesis ; Pergamon Press : Oxford , 1993 .
  • Najera , C. ; Yus , M. Desulfonylation reactions: Recent developments . Tetrahedron. 1999 , 55 , 10547 – 10658 .
  • (a) Kirsteen Gordon , K. ; Balasubramanian , S. Solid-phase synthesis–designer linkers for combinatorial chemistry: A review . J. Chem. Technol. Biotechnol. 1999 , 74 , 835 – 851 ; (b) Blaney , P. ; Grigg , R. ; Sridharan , V. Traceless solid-phase organic synthesis . Chem. Rev. 2002 , 102 , 2607 – 2624 ; (c) McAllister , L. A. ; McCormick , R. A. ; Procter , D. J. Sulfide- and selenide-based linkers in phase tag–assisted synthesis . Tetrahedron. 2005 , 61 , 11527 – 11576 .
  • (a) Cheng , W. C. ; Lin , C. C. ; Kurth , M. J. Dimsyl anion in the monoalkylation of solid-phase alkyl sulfones . Tetrahedron Lett. 2002 , 43 , 2967 – 2970 ; (b) Hwang , S. H. ; Olmstead , M. M. ; Kurth , M. J. Solid-phase synthesis of an isoxazolinopyrrole library . J. Comb. Chem. 2004 , 6 , 142 – 148 .
  • (a) Li , W. W. ; Lam , Y. L. Solid-phase synthesis of 3,4-dihydro-1H-pyrimidine-2-ones using sodium benzenesulfinate as a traceless linker . J. Comb. Chem. 2005 , 7 , 721 – 725 ; (b) Kong , K.-H. ; Tan , C.-K. ; Lam , Y. L. Traceless solid-phase synthesis of 6-amino- and 6-hydroxyimino-1,3,5-triazine-2,4-diones and 1,3,5-triazine-2,4,6-triones . J. Comb. Chem. 2009 , 11 , 1050 – 1060 .
  • (a) Huang , W. ; Cheng , S. ; Sun , W. 2-Polystyrylsulfonyl ethanol supports for the solid-phase syntheses of hydantoins and ureas . Tetrahedron Lett. 2001 , 42 , 1973 – 1974 ; (b) D'herde , J. N. P. ; De Clercq , P. J. Carbon–carbon bond formation on solid support: Application of the classical Julia–Lythgoe olefination . Tetrahedron Lett. 2003 , 44 , 6657 – 6659 ; (c) Hwang , J. Y. ; Choi , H.-S. ; Lee , D.-H. ; Gong , Y.-D. Solid-phase synthesis of 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives via selective, reagent-based cyclization of acyldithiocarbazate resins . J. Comb. Chem. 2005 , 7 , 816 – 819 ; (d) McAllister , L. A. Turner , K. L. ; Brand , S. ; Stefaniak , M. ; Procter , D. J. Solid-phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2 . J. Org. Chem. 2006 , 71 , 6497 – 6507 ; (e) Xie , J. W. ; Sun , J. ; Zhang , G. L. ; Houghten , R. A. ; Yu , Y. P. Traceless approach for the solid-phase parallel synthesis of trisubstituted oxindoles . J. Comb. Chem. 2007 , 9 , 566 – 568 ; (f) Chang , Y.-F. ; Jiang , Y.-R. ; Cheng , W.-C. Traceless sulfone linker cleavage triggered by ozonolysis: Solid-phase synthesis of diverse a-b-unsaturated carbonyl compounds . Tetrahedron Lett. 2008 , 49 , 543 – 547 ; (g) Lee , T. ; Lee , T. D. ; Lee , I. Y. ; Gong , Y.-D. Solid-phase synthesis of thiazolo[4,5-b]pyridine derivatives using Friedländer reaction . J. Comb. Chem. 2010 , 12 , 95 – 99 .
  • (a) Sheng , S.-R. ; Huang , P.-G. ; Zhou , W. ; Luo , H.-R. ; Lin , S.-Y. ; Liu , X.-L. A facile solid-phase synthesis of substituted 2(5H)-furanones with sulfone traceless linker. Synlett. 2004, 2603–2605; (b) Sheng , S.-R. ; Xu , L. ; Zhang , X.-L. ; Liu , X.-L. ; Wei , M.-H. Solid-phase synthesis of substituted butenolides and butyrolactones using a traceless sulfone linker. J. Comb. Chem. 2006, 8, 805–807; (c) Liu , X.-L. ; Sheng , S.-R. ; Zhou , W. ; Wang , Q.-Y. ; Zhang , X.-L. ; Gong , B. A facile solid-phase synthesis of cycloalkylphosphonates and 1-cycloalkenylphosphonates using polymer-supported phenylsulfonylmethylphosphonates. Synth. Commun. 2007, 37, 119–127; (d) Yu , L.-M. ; Tang , N. ; Sheng , S.-R. ; Chen , R.-B. ; Liu , X.-L. ; Cai , M.-Z. Solid-phase organic synthesis of aryl vinyl ethers using sulfone-linking strategy. Chin. J. Chem. 2012, 30, 1027–1030.
  • Farrall , M. J. ; Frėchet , J. M. J. Bromination and lithiation: Two important steps in the functionalization of polystyrene resins . J. Org. Chem. 1976 , 41 , 3877 – 3882 .
  • Heinonen , P. ; Lönnberg , H. A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-aikoxy-l,2,3,4-tetrahydroisoquinolines via Mitsunobu reaction . Tetrahedron Lett. 1997 , 38 , 8569 – 8572 .
  • Xu , J. ; Hamme II , A. T. Efficient access to isoxazoles from alkenes . Synlett. 2008 , 919 – 923 .
  • Di Nunno , L. ; Vitale , P. ; Scilimati , A. ; Simone , L. ; Capitelli , F. Stereoselective dimerization of 3-arylisoxazoles to cage-shaped bis-β-lactams syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.0 2,5]-octan-4,8-diones induced by hindered lithium amides . Tetrahedron 2007 , 63 , 12388 – 12395 .

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