Solid-Phase Organic Synthesis of Methyl Isoxazole-5-carboxylates Based on Wang Resin–Bound 1-Phenylselenoacrylate

REFERENCES

• Recent reviews on SPOS : (a) Guillier , F. ; Orain , D. ; Bradley , M. Linkers and cleavage strategies in solid-phase organic synthesis, and combinatorial chemistry . Chem. Rev. 2000 , 100 , 2091 – 2158 ; (b) Sammelson , R. E. ; Kurth , M. J. Carbon-carbon bond-forming solid-phase reactions, part II . Chem. Rev. 2001 , 101 , 137 – 202 (c) Blaney , P. ; Grigg , R. ; Sridharan , V. Traceless solid-phase organic synthesis . Chem. Rev. 2002 , 102 , 2607 – 2624 .
   PubMed Web of Science ®Google Scholar
• Baraldi , P. G. ; Barco , A. ; Benetti , S. ; Pollini , G. P. ; Simoni , D. Synthesis of natural products via isoxazoles . Synthesis 1987 , 857 – 869 .
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 .
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 .
   PubMed Web of Science ®Google Scholar
• (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) Dowald , F. Z. Organic Synthesis on Solid Phase, Wiley-VCH: Weinheim, 2002.
   PubMed Web of Science ®Google Scholar
• (a) Shen , D. M. ; Shu , M. ; Chapman , K. T. Versatile and efficient solid-phase syntheses of pyrazoles and isoxazoles . Org. Lett. 2000 2 , 2789 – 2792 ; (b) Marzinzik , A. L. ; Felder , E. R. Solid-support synthesis of highly functionalized pyrazoles and isoxazoles: Scaffolds for molecular diversity . Tetrahedron Lett. 1996 , 37 , 1003 – 1006 .
   PubMed Web of Science ®Google Scholar
• (a) Yedidia , V. ; Leznoff , C. C. Regioselectivity in cycloaddition reactions on solid phases. Can. J. Chem. 1980, 58, 1144–1150; (b) Pei , Y. Z. ; Moos , W. H. Post-modification of peptoid side chains: [3 + 2] Cycloaddition of nitrile oxides with alkenes and alkynes on the solid phase. Tetrahedron Lett. 1994, 35, 5825–5828; (c) Haino , T. ; Tanaka , M. ; Ideta , K. ; Kubo , K. ; Mori , A. ; Fukazawa , Y. Solid-phase synthesis of liquid crystalline isoxazole library. Tetrahedron Lett. 2004, 45, 2277–2279; (d) Kantorowski , E. J. ; Kurth , M. J. Solid-phase synthesis of isoxazoles and isoxazolines: En route to a new class of ionophores. J. Org. Chem. 1997, 62, 6797–6803; (e) Gao , D. ; Zhai , H. M. ; Parvez , M. ; Back , T. G. 1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports. J. Org. Chem. 2008, 73, 8057–8068.
   Web of Science ®Google Scholar
• (a) Shankar , B. B. ; Yang , D. Y. ; Girton , S. ; Ganguly , A. K. One-pot solid-phase synthesis of isoxazolines . Tetrahedron Lett. 1998 , 39 , 2447 – 2448 ; (b) Alonso , C. ; Nantz , M. H. Kurth , M. J. β-Dimethylphenylsilylethyl esters: A linker for solid-phase chemistry . Tetrahedron Lett. 2000 , 41 , 5617 – 5622
   Web of Science ®Google Scholar
• (a) Barrett , A. G. M. ; Procopiou , P. A. ; Voigtmann , U. Solid-phase synthesis of isoxazoles using vinyl ethers as chameleon catches . Org. Lett. 2001 , 3 , 3165 – 3168 ; (b) Engler , T. A. In Studies in Natural Product Chemistry; Attaur-Rahman (Ed)., Elsevier Science: New York, 1995; Vol. 16.
   PubMed Web of Science ®Google Scholar
• (a) Reich , H. J. Functional group manipulation using organoselenium reagents . Acc. Chem. Res. 1979 , 12 ( 1 ), 22 – 30 ; (b) Paulmier , C. (Ed). Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
   Web of Science ®Google Scholar
• (a) Huang , X. ; Xu , W. M. Use of selenium-bound resin for the solid-phase synthesis of substituted isoxazolyl-substituted (E)-olefins . Org. Lett. 2003 , 5 , 4649 – 4652 ; (b) Xu , W. M. ; Wang , Y. G. ; Miao , M. Z. ; Huang , X. A novel cleavage for polystyrene-supported selenium resins: An efficient route to 3,5-disubstituted isoxazolines and their derivatives . Synthesis 2005 , 2143 – 2146 ; (c) Xu , W. M. ; Huang , X. ; Tang , E. Solid-phase synthesis of 1,2-diheterocyclic-substituted (E)-olefins from a supported selenium resin . J. Comb. Chem. 2005 , 7 , 726 – 733 (d) Huang , X. ; Wang , Y. G. Solid-phase synthesis of linked heterocycles from a selenopolystyrene resin . J. Comb. Chem. 2007 , 9 , 121 – 130 ; (e) Wang , Y. G. ; Xu , W. M. ; Huang , X. An efficient solid-phase synthesis of substituted isoxazole, triazole, and cycloalkadiene derivatives using supported selenium resin . Synthesis 2007 , 28 – 32 ; (f) Cao , J. ; Huang , X. Solid-phase synthesis of heterocyclic nucleoside analogues: Substituted uracils tethered to isoxazoles, isoxazolines, and triazoles from a selenopolystyrene resin . J. Comb. Chem. 2008 , 10 , 526 – 533 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Sheng , S. R. ; Huang , F. F. ; Lin , S. Y. ; Liu , X. L. ; Huang , X. Solid-phase synthesis of 3-hydroxy-2-methylenealkanoates and their derivatives using polymer-supported α-phenylselenopropionate . Synthesis 2007 , 1373 – 1377 .
   Web of Science ®Google Scholar
• Yan , B. ; Kumaravel , G. ; Anjaria , H. ; Wu , A. ; Petter , R. C. ; Jewell , C. F. ; Wareing , J. R. Infrared spectrum of a single resin bead for real-time monitoring of solid-phase reactions . J. Org. Chem. 1995 , 60 , 5736 – 5738 .
   Web of Science ®Google Scholar
• Huang , X. ; Xu , J. F. Solid-phase synthesis of 2,5-dihydro-1H-pyrroles, 1,3-dioxo-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazoles, and 1,4-dioxo-1,2,3,4,6,8a-hexa-hydropyrrolo[1,2-a]pyrazines using a supported selenium resin . J. Comb. Chem. 2009 , 11 , 350 – 354 .
   PubMed Web of Science ®Google Scholar
• (a) Torsell , K. G. B. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis ; VCH : New York , 1998 ; (b) Padwa , A. ; Pearson , W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products . In The Chemistry of Heterocyclic Compounds ; John Wiley & Sons : New York , 2002 ; Vol. 59 . (c) Pinho e Melo , T. M. V. D. Recent advances on the synthesis and reactivity of isoxazoles. Curr. Org. Chem. 2005, 9, 925-958 .
   Google Scholar
• Dadiboyena , S. ; Xu , J. P. ; Hamme II , A. T. Isoxazoles from 1,1-disubstituted bromoalkenes. Tetrahedron Lett. 2007, 48, 1295–1298.
   PubMed Web of Science ®Google Scholar
• Hamme , A. T. II ; Xu , J. ; Wang , J. ; Cook , T. ; Ellis , E. Synthesis of functionalized 5,5-disubstituted isoxazolines via 1,3-dipolar cycloaddition reactions of geminal disubstituted alkenes . Heterocycles 2005 , 65 , 2885 – 2895 .
   Web of Science ®Google Scholar