Domino [3+2] cycloaddition/annulation reactions of β-(2-aminophenyl)-α,β-ynones with nitrile oxides: Synthesis of isoxazolo[4,5-c]quinolines

European Journal of Organic Chemistry

Volumn , Issue 8, 2003, Pages 1423-1427

  Abbiati, Giorgio ^a   Arcadi, Antonio ^b   Marinelli, Fabio ^b   Rossi, Elisabetta ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

Alkynes; Cycloaddition; Domino reactions; Polycycles

Indexed keywords

4 (4 ACETYLPHENYL) 3 (4 FLUOROPHENYL)ISOXAZOLO[4,5 C]QUINOLINE; 4 (4 ACETYLPHENYL) 3 (4 METHOXYPHENYL)ISOXAZOLO[4,5 C]QUINOLINE; 4 (4 CHLOROPHENYL) 3 (4 NITROPHENYL)ISOXAZOLO[4,5 C]QUINOLINE; 4 (4 CHLOROPHENYL) 3 ETHYLISOXAZOLO[4,5 C]QUINOLINE; 4 (4 CHLOROPHENYL) 3 PHENYLISOXAZOLO[4,5 C]QUINOLINE; 4 (4 CHLOROPHENYL) 3 STYRYLISOXAZOLO[4,5 C]QUINOLINE; 4 (CHLOROPHENYL) 3 (1 ETHYLPROPYL)ISOXAZOLO[4,5 C]QUINOLINE; 4 CHLORO 2 (4 CHLOROPHENYL)QUINOLINE; AMINOPHENOL DERIVATIVE; BETA (2 AMINOPHENYL) ALPHA,BETA YNONE DERIVATIVE; ETHYL 4 (3 ETHYLISOXAZOLO[4,5 C]QUINOLIN 4 YL)BENZOATE; ETHYL 4 (3 STYRYLISOXAZOLO[4,5 C]QUINOLIN 4 YL)BENZOATE; ETHYL 4 (4 ACETYLPHENYL)ISOXAZOLO[4,5 C]QUINOLINE 3 CARBOXYLATE; ETHYL 4 [3 (TRIFLUOROMETHYL)PHENYL]ISOXAZOLO[4,5 C]QUINOLINE 3 CARBOXYLATE; ISOXAZOLO[4,5 C]QUINOLINE DERIVATIVE; NITRILE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ENZYME INHIBITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037547164     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390200     Document Type: Article

References (16)

1. G. Abbiati, A. Arcadi, F. Marinelli, E. Rossi, Synthesis 2002, 13, 1912-1916 and references therein.
2. [2a] E. Rossi, G. Abbiati, A. Arcadi, F. Marinelli, Tetrahedron Lett. 2001, 42, 3705-3708.
3. [2b] A. Arcadi, F. Marinelli, E. Rossi, Tetrahedron 1999, 55, 13233-13250.
4. [3a] K. Gorlitzer, J. Fabian, P. Froheberg, G. Drutkowski, Pharmazie 2002, 57, 243-247.
5. [3a] L. Savini, L. Chiasserini, C. Pellerano, W. Filippelli, G. Falcone, Farmaco, Ed. Sci. 2001, 56, 939-956.
6. [4a] B. Staskun, J. Org. Chem. 1966, 31, 2674-2676.
7. [4a] B. Venugopalan, C. P. Bapat, E. P. de Souza, N. J. de Souza, J. Heterocycl. Chem. 1991, 28, 337-339.
8. [5a] R. Bonjouklian, J. S. York, PCT Int. Appl. WO 2002000624, 2002; Chem. Abstr. 2002, 136, 69745.
9. [5b] R. Bonjouklian, J. D. Cohen, J. M. Gruber, D. W. Johnson, L. N. Jungheim, J. S. Kroin, P. A. Lander, H. Lin, M. C. Lohman, B. S. Muehl, B. H. Norman, V. F. Patel, M. E. Richett, K. J. Thrasher, S. Vepachedu, W. T. White, Y. Xie, J. S. York, B. L. Parkhurst, PCT Int. Appl. WO 2001046199, 2001; Chem. Abstr. 2001, 135, 76865.
10. [5c] R. Bonjouklian, D. W. Johnson, P. A. Lander, M. C. Lohman, V. F. Patel, S. Vepachedu, Y. Xie, PCT Int. Appl. WO 2001027116, 2001; Chem. Abstr. 2001, 134, 311201.
11. [5d] B. Buettelmann, T. Godel, L. Gross, M-P. Heitz Niedhart, C. Riemer, R. Wyler, PCT Int. Appl. No WO 9532205, 1995; Chem. Abstr. 1996, 124, 232481.
12. F. Gatta, M. R. Del Giudice, M. Pomponi, M. Marta, Heterocycles 1992, 34, 991-1004.
13. P. Grünanger, P. Vita-Finzi, in The Chemistry of Heterocyclic Compounds (Eds.: A. Weissberger, E. C. Taylor), John Wiley, New York, 1999, vol. 49.
14. [8a] A. Gasco, A. J. Bulton in Advances in Heterocyclic Chemistry (Ed.: A. L. Katritzky), Academic, Orlando, 1981, vol. 29.
15. [8b] W. Sliwa, A. Thomas, Heterocycles 1985, 23, 399-416.
16. S. Cacchi, G. Fabrizi, F. Marinelli, Synlett 1999, 4, 401-404.