Novel microwave-assisted one-pot synthesis of isoxazoles by a three-component coupling-cycloaddition sequence

Synthesis

Volumn , Issue 2, 2008, Pages 293-303

  Willy, Benjamin ^a   Rominger, Frank ^b   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Cross couplings; Cycloaddition; Isoxazole; Microwave reaction

Indexed keywords

ALKYNES; CROSS-COUPLINGS; ISOXAZOLE; MICROWAVE REACTION;

MICROWAVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

(5 BUTYL 3 4 TOLYLISOXAZOL 4 YL)(THIOPHEN 2 YLMETHANONE; 1 [3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL] 2,2 DIMETHYLPROPAN 1 ONE; 1 [3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL] 3 PHENYLPROP 2 EN 1 ONE; 4 METHOXYPHENYL [5 PROPYL 3 (THIOPHEN 2 YL)ISOXAZOL 4 YL]METHANONE; [3 (4 METHOXYPHENYL) 5 [10 METHYL 10H PHENOTHIAZIN 3 YL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3 (4 METHOXYPHENYL) 5 [4 [PYRROLIDIN 1 YL]PHENYL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3 (4 METHOXYPHENYL) 5 [4 NITROPHENYL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3 (4 METHOXYPHENYL) 5 [[TETRAHYDRO 2H PYRAN 2 YLOXY]METHAL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL] 4 (TRIFLUOTOMETHYL)PHENYLMETHANONE; [3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3 (ANTHRACEN 9 YL) 5 BUTYLISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [3,5 BIS(4 METHOXYPHENYL)ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [5 (3,4 DIMETHOXYPHENYL) 3 [4 METHOXYPHENYL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [5 (4 CHLOROPHENYL) 3 [4 METHOXYPHENYL]ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [5 BUTYL 3 (3,4 DIMETHOXYPHENYL)ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [5 BUTYL 3 (4 METHOXYPHENYL)ISOXAZOL 4 YL]4 CHLOROPHENYLMETHANONE; [5 BUTYL 3 (4 METHOXYPHENYL)ISOXAZOL 4 YL]4 METHOXYPHENYLMETHANONE; [5 BUTYL 3 (4 METHOXYPHENYL)ISOXAZOL 4 YL]4 NITROPHENYLMETHANONE; [5 BUTYL 3 (4 METHOXYPHENYL)ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; [5 BUTYL 3 (4 NITROPHENYL)ISOXAZOL 4 YL]4 NITROPHENYLMETHANONE; [5 DECYL 3 (4 METHOXYPHENYL)ISOXAZOL 4 YL]THIOPHEN 2 YLMETHANONE; ALKYNE DERIVATIVE; CHLORIDE; CYCLOHEXENYL[3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL]METHANONE; CYCLOPROPYL[3 (4 METHOXYPHENYL) 5 TRIMETHYLSILYLISOXAZOL 4 YL)METHANONE; ISOXAZOLE DERIVATIVE; METHYL 4 [3 (4 METHOXYPHENYL) 4 THIOPHENE 2 CARBONYLISOXAZOL 5 YL]BENZOATE; NITRILE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; MICROWAVE RADIATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION;

EID: 38849179369     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1000856     Document Type: Article

References (32)

1. For a review, see: Carlsen, L.; Döpp, D.; Döpp, H.; Duus, F.; Hartmann, H.; Lang-Fugmann, S.; Schulze, B.; Smalley, R. K.; Wakefield, B. J. In Houben-Weyl, Methods in Organic Chemistry, Vol. E8a; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1992, 45-204.
2. Rowley, M.; Broughton, H. B.; Collins, I.; Baker, R.; Emms, F.; Marwood, R.; Patel, S.; Ragan, C. I. J. Med. Chem. 1996, 39, 1943.
3. Frolund, B.; Jorgensen, A. T.; Tagmose, L.; Stensbol, T. B.; Vestergaard, H. T.; Engblom, C.; Kristiansen, U.; Sanchez, C.; Krogsgaard-Larsen, P.; Liljefors, T. J. Med. Chem. 2002, 45, 2454.
4. Daidone, G.; Raffa, D.; Maggio, B.; Plescia, F.; Cutuli, V. M. C.; Mangano, N. G.; Caruso, A. Arch. Pharm. Pharm. Med. Chem. 1999, 332, 50.
5. (a) Talley, J. J. Prog. Med. Chem. 1999, 13, 201.
6. (b)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. J. Med. Chem. 2000, 43, 775.
7. Giovannoni, M. P.; Vergelli, C.; Ghelardini, C.; Galeotti, N.; Bartolini, A.; Kal Piaz, V. J. Med. Chem. 2003, 46, 1055.
8. Li, W.-T.; Hwang, D.-R.; Chen, C.-P.; Shen, C.-W.; Huang, C.-L.; Chen, T.-W.; Lin, C.-H.; Chang, Y.-L.; Chang, Y.-Y.; Lo, Y.-K.; Tseng, H.-Y.; Lin, C.-C.; Song, J.-S.; Chen, H.-C.; Chen, S.-J.; Wu, S.-H.; Chen, C.-T. J. Med. Chem. 2003, 46, 1706.
9. For a recent review, see: Wakefield, B. J. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Vol. 11; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2001, 229.
10. Bandiera, T.; Grünanger, P.; Albini, F. M. J. Heterocycl. Chem. 1992, 29, 1423.
11. Cuadrado, P.; Gonzalez-Nogal, A. M.; Valero, R. Tetrahedron 2002, 58, 4975.
12. Vicentini, C. B.; Verones, A. C.; Poli, T.; Guarneri, M.; Giori, P.; Ferretti, V. J. Heterocycl. Chem. 1990, 27, 1481.
13. He, Y.; Lin, N.-H. Synthesis 1994, 989.
14. (a) Barber, G. N.; Olofson, R. A. J. Org. Chem. 1978, 43, 3015.
15. (b) Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
16. (a) Denmark, S. E.; Kallemeyn, J. M. J. Org. Chem. 2005, 70, 2839.
17. (b) Jaeger, V.; Colinas, P. A. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, In Chemistry of Heterocyclic Compounds, Vol. 59; Padwa, A.; Pearson, W. H., Eds.; Wiley: Hoboken, 2002, 361.
18. (a) Müller, T. J. J. In Targets in Heterocyclic Systems, Vol. 10; Attanasi, O. A.; Spinelli, D., Eds.; Società Chimica Italiana: Rome, 2006, 54.
19. (b) Müller, T. J. J. Chimica Oggi/Chemistry Today 2007, 25, 70.
20. For a recent review on multi-component synthesis of heterocycles by transition-metal catalysis, see: D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev.; 2007, 36, 1095.
21. Rotaru, A. V.; Druta, I. D.; Oeser, T.; Müller, T. J. J. Helv. Chim. Acta 2005, 88, 1798.
22. Toda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777.
23. (a) Karpov, A. S.; Müller, T. J. J. Org. Lett. 2003, 5, 3451.
24. (b) Karpov, A. S.; Müller, T. J. J. Synthesis 2003, 2815.
25. (c) Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Angew. Chem. Int. Ed. 2005, 44, 6951.
26. (d) Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Eur. J. Org. Chem. 2006, 2991.
27. For important reviews on 1,3-dipolar cycloadditions, see: (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565.
28. (b) Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; John Wiley & Sons: New York, 1984.
29. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-661680 (5w), and CCDC-661681 (6a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
30. Becker, H. G. O.; Beckert, R.; Domschke, G.; Fanghänel, E.; Habicher, W. D.; Metz, P.; Pavel, D.; Schwetlick, K. Organikum; Wiley-VCH: Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 2001, 21st ed.
31. (a) Liu, K.-C.; Shelton, R. B.; Howe, R. K. J. Org. Chem. 1980, 45, 3916.
32. (b) Shaw, K. N.F.; McMillan, A.; Gudmundson, A. G.; Armstrong, M. D. J. Org. Chem. 1958, 23, 1171.