Novel method for soluble-polymer-supported synthesis of 3,4,5-trisubstituted isoxazoles

Synthetic Communications

Volumn 38, Issue 4, 2008, Pages 583-594

  Shang, Yongjia ^a   Ren, Lianbing ^a   Wu, Jianwei ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

Author keywords

Dehydrogenation; Isoxazoles; Isoxazolines; Poly(ethylene glycol)

Indexed keywords

3,4,5 ISOXAZOLE DERIVATIVE; CHALCONE DERIVATIVE; ISOXAZOLE DERIVATIVE; MACROGOL; METHOXIDE SODIUM; NITRILE OXIDE; POLYMER; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEHYDROGENATION; INFRARED SPECTROSCOPY; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 38949131211     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701797988     Document Type: Article

References (31)

1. (a) Coutouli-Argyropoulou, E.; Lianis, P.; Mitakou, M.; Giannoulis, A.; Nowak, J. 1,3-Dipolar cycloaddition approach to isoxazole, isoxazoline andisoxazolidine analogues of C-nucleosides related to pseudouridine. Tetrahedron 2006, 62, 1494-1501;
2. (b) Trond, V.; Hansen, T. V.; Wu, P.; Fokin, V. V. One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles. J. Org. Chem. 2005, 70, 7761-7764;
3. (c) Nantermet, P. G.; Barow, J. C.; Lundell, G. F.; Pellicore, J. M.; Rittle, K. E.; Young, M. B.; Friedanger, R. M.; Connoly, T. M.; Condra, C.; Karczewski, J.; Bednar, R. M.; Gaul, S. L.; Gould, R. J.; Prendergast, K.; Selnick, H. G. Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1). Bioorg. Med. Chem. Lett. 2002, 12, 319;
4. (d) Pruitt, J. R.; Pinto, D. J.; Estrella, M. J.; Bostrom, L. L.; Knabb, R. M.; Wong, P. C.; Wright, M. R.; Wexler, R. R. Isoxazolines and isoxazoles as factor Xa inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 685;
5. (e) Xue, C. B.; Roderick, J.; Mousa, S. A.; Olson, R. E.; Degrado, W. F. Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists. Bioorg. Med. Chem. Lett. 1998, 8, 3499;
6. (f) Baraldi, P. G.; Barco, A.; Bennetti, S.; Pollini, G. P.; Simoni, D. Synthesis of natural products via isoxazoles. Synthesis 1987, 857-869.
7. (a) Epple, R.; Azimioara, M.; Russo, R.; Xie, Y.; Wang, X.; Cow, C.; Wityak, J.; Karanewsky, D.; Bursulay, B.; Tuntland, T.; Gerken, A.; Iskandar, M.; Saez, E.; Seidel, H. M.; Tian, S.-S. 3,4,5-Trisubstituted isoxazoles as novel PPAR? agonists: Part 2. Bioorg. Med. Chem. Lett. 2006, 16, 5488-5492;
8. (b) Epple, R.; Russo, R.; Azimioara, M.; Cow, C.; Xie, Y.; Wang, X.; Wityak, J.; Karanewsky, D.; Gerken, A.; Iskandar, M.; Saez, E.; Seidel, H. M.; Tian, S.-S. 3,4,5-Trisubstituted isoxazoles as novel PPAR? agonists: Part 1. Bioorg. Med. Chem. Lett. 2006, 16, 4376-3480.
9. Denmark, S. C.; Kallemeyn, J. M. Synthesis of 3,4,5-trisubstitued isoxazoles via sequential [3 + 2] cycloaddition/silicon-based cross-coupling reactions. J. Org. Chem. 2005, 70, 2839-2842.
10. (a) Gothelf, K. V.; Jørgensen, K. A. Asymmetric 1,3-dipolar cycloaddition reactions. Chem. Rev 1998, 98, 863-909;
11. (b) Kobayashi, S.; Jørgensen, K. A. Cycloaddition Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
12. (a) Auwers, K. V.; Muller, H. Über isoxazoline und isoxazole. J. Prakt. Chem. 1933, 137, 102;
13. (b) Stagno d'Alcontres, G. The chemistry of nitrile oxides. Gazz. Chim. Ita. 1952, 82, 627.
14. Barco, A.; Benetti, S.; Pollini, G. P.; Beraldi, P. G. Active ?-manganese dioxide promoted conversion of 4,5-dihydro-1,2-oxazoles to 1,2-oxazoles. Synthesis 1977, 837.
15. (a) Padmavathi, V.; Sivajyothi, G.; Sreedhar, N. Y.; Reddy, K. V.; Padmaja, A. Synthesis of mono and bis pyrazolines and iso-oxazolines by 1,3-dipolar cycloaddition of dipolar reagents to 3,3′-[1,4-/1,3-phenylene] bis [1-aryl-2-propenone] in the presence of chloramine-T. Indian J. Chem., Sect. B 2004, 43B (11), 2395-2400;
16. (b) Padmavathi, V.; Jyothi, G. S.; Sreedhar, N. Y.; Reddy, K. V.; Reddy, T. V. R.; Reddy, D. B. Cycloaddition of bis-1,3-dipolar reagents to 1,3-diarylprop-2-en-1-ones. Heteroatom Chem. 2003, 14 (4), 379-383.
17. (a) Yadav, P. P.; Ghufran Ahmad, G.; Maurya, R. An efficient route for commercially viable syntheses of furan- and thiophene-anellated ?-hydroxychalcones. Tetrahedron Lett. 2005, 46, 5621-5624;
18. (b) Padmavathi, V.; Jagan Mohan Reddy, B. J. M.; Venkata Subbaiah, D. R. C. Bischalcones - synthons for a new class of bis(heterocycles). New J. Chem. 2004, 28, 1479-1483.
19. El-Kasaby, M. A.; Salem, M. A. I. Synthesis of 1,2,4 triazolo and Nicotino-nitrile and their effect on bio-mphalaria alexandrina snail enzymes. Egypt. J. Chem. 1981, 23, 123-136.
20. (a) Shankar, B. B.; Yang, D. Y.; Girton, S.; Ganguly, A. K. One pot solid phase synthesis of isoxazolines. Tetrahedron Lett. 1998, 39, 2447;
21. (b) Batra, S.; Rastogi, S. K.; Kundu, B.; Patra, A.; Bhaduri, A. P. A novel isoxazole-based scaffold for combinatorial chemistry. Tetrahedron Lett. 2000, 41, 5971.
22. (a) Chao, Q.; Kurth, M. Solid-phase synthesis of 5-isoxazol-4-yl-[1,2,4] oxadiazoles. J. Org. Chem. 2004, 69, 1470-1474;
23. (b) Luca, L. D.; Giacomelli, G.; Riu, A. Solid-phase synthesis of isoxazole-based amino acids: a new scaffold for molecular diversity. J. Org. Chem. 2001, 66, 6823.
24. (a) Shang, Y. J.; Jin, J.; Wang, Y. G. Nitrile oxides cycloadditions to PEG-bounded alkene dipolarophiles. React. Funct. Poly. 2006, 66, 447-453;
25. (b) Shang, Y. J.; Yuan, L. L.; Wang, Y. G. One-pot synthesis of isoxazolines and isoxazoles using soluble polymer-supported aldehyde. J. Chem. Res., Synop. 2004, 5, 336-338;
26. (c) Shang, Y. J.; Wang, Y. G. Soluble polymer-supported synthesis of isoxazoles. Tetrahedron Lett. 2002, 43, 2247-2249;
27. (d) Shang, Y. J.; Wang, Y. G. Synthesis of isoxazolines and isoxazoles using poly(ethylene glycol) as support. Synthesis 2002, 12, 1663-1668.
28. Reviews on liquid-phase organic synthesis (LPOS); (a) Toy, P. H.; Janda, K. D. Soluble polymer supported organic synthesis. Acc. Chem. Res. 2000, 33, 546-554;
29. (b) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Soluble polymer-supported synthesis of lactams on a modified poly(ethylene glycol). Chem. Eur. J. 2000, 6, 133-138;
30. (c) Harwig, C. W.; Gravert, D. J.; Janda, K. D. Synthesis of isoxazolines and isoxazole. Chemtracts: Org. Chem. 1999, 12, 1-26;
31. (d) Gravert, D. J.; Janda, K. D. Organic synthesis on soluble polymer supports: liquid-phase methodologies. Chem. Rev. 1997, 97, 489-509.