Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles

Heterocycles

Volumn 63, Issue 1, 2004, Pages 63-74

  Miklós, Ferenc ^a   Kanizsai, Iván ^a   Thomas, Steffen ^b   Kleinpeter, Erich ^b   Sillanpää, Reijo ^c   Stájer, Géza ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF POTSDAM   (Germany)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 1 (4 TOLYLHEXAHYDRO 4,7 EPOXYBENZOFURAN 3 ONE); 1,4 EPOXY 9,12 METHANO 5 (4 TOLYL 8H 1,2,3,4,4A,8A,9,10,11,12,12A,13B DODECAHYDROPHTHALAZINO[1,2 B]QUINAZOLIN 8 ONE); 3 (4 TOLUOYL 7 OXABICYCLO[2.2.1]HEPTANE 2 CARBOXYLIC ACID); 8,11 EPOXY 7 (4 TOLYL 7A,8,9,10,11,11A HEXAHYDRO 4H PYRIMIDO[2,1 A]PHTHALAZIN 4 ONE); ALKANOLAMINE; BENZOFURAN DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; DIAMINE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NORBORNANE DERIVATIVE; OXANORBORNANE DERIVATIVE; OXANORBORNANEDICARBOXYLIC ACID ANHYDRIDE; PHENYLENEDIAMINE; QUINAZOLINE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY;

EID: 0347654910     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9916     Document Type: Article

References (30)

1. G. Stájer, A.E. Szabó, and P. Sohár, Heterocycles, 1999, 51, 1849.
2. G. Bernáth, F. Miklós, G. Stájer, P. Sohár, Z. Böcskei and D. Menyhárt, J. Heterocycl. Chem., 1998, 35, 201.
3. G. Stájer, F. Csende, G. Bernáth, and P. Sohár, Heterocycles, 1994, 37, 883.
4. F. Miklós, P. Sohár, A. Csámpai, R. Sillanpää, M. Péter, and G. Stájer, Heterocycles, 2002, 57, 2309.
5. H. Orzalesi, P. Chevallet, G. Berge, M. Boucard, J. J. Serrano, G. Privat, and C. Andrary, Eur. J. Med.-Chim. Ther., 1978, 13, 259.
6. W. Curran and A. Ross, J. Med. Chem., 1974, 17, 273.
7. C. Andrés, J. Nieto, R. Pedrosa, and M. Vicente, J. Org. Chem., 1998, 63, 8570.
8. C. Rogers and B. A. Keay, Tetrahedron Lett., 1989, 30, 1349.
9. B. A. Keay and P. W. Dibble, Tetrahedron Lett., 1989, 30, 1045.
10. H. Finch, L. M. Harwood, G. M. Robertson, and R. C. Sewell, Tetrahedron Lett., 1989, 30, 2585.
11. R. N. Warrener, D. N. Butler, W. Y. Liao, I. G. Pitt, and R. A. Russel, Tetrahedron Lett., 1991, 32, 1889.
12. O. Diels and S. Olsen, J. Prakt. Chem., 1940, 156, 285.
13. H. Wilson, R. L. Jones, C. G. Marr, and G. Muir, Eur. J. Med. Chem., 1988, 23, 359.
14. P. Cannone, D. Belanger, and G. Lemay, J. Org. Chem., 1982, 47, 3953.
15. O. Diels and K. Alder, Ber., 1929, 62, 554.
16. A. Winston, J. C. Sharp, K. E. Atkins, and D. E. Battin, J. Org. Chem., 1967, 32, 2166.
17. E. Pretsch, T. Clerc, J. Seibl, W. Simon Tabellen zur Strukturaujklärung organischer Verbindungen, Springer-Verlag, Heidelberg, 1990.
18. Y. Fukazava, S. Usui, K. Tanimoto, and Y. Hirai, J. Am. Chem. Soc., 1994, 116, 8169.
19. C. A. Hunter and M. J. Packer, Chem. Eur. J., 1999, 5, 1891.
20. S. P. Brown, T. Schaller, V. P. Seelbach, F. Koziol, C. Ochsenfeld, F. G. Klámer, and H. W. Spiess, Angew. Chem., Int. Ed., 2001, 40, 717.
21. GAUSSIAN-98, Revision A. 7.: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. Strain, C. O. Farkas, J.Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Ayala, Y. Q. Cui, K. D. Morokuma, K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, L. Komaromi, R. Gomperts, L. R. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, and A. Gaussian, Inc., Pittsburgh PA, 1998.
22. W. J. Hehre, L. Random, P. V. R. Schleyer, and J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986.
23. J. R. Ditchfield, Mol. Phys., 1974, 27, 789.
24. J. P. Cheeseman, G. W. Trucks, T. A. Keith, and M. J. Frisch, J. Chem. Phys., 1996, 104, 5497.
25. SYBYL 6.7; Tripos Inc. St. Louis MO 63144, S. Hanley Road 303, 2001.
26. S. Klod and E. Kleinpeter, J. Chem. Soc., Perkin Trans. 2, 2001, 1893.
27. Z. Otwinowski and W. Minor, Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A (ed. by C. W. Carter, Jr. and R. M. Sweet), pp. 307-326, Academic Press, New York, 1997.
28. A. Altomare, M. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Pilodori, and M. Camalli, J. Appl. Cryst., 1994, 27, 435.
29. G. M. Sheldrick, SHELX-97, University of Göttingen, Germany, 1997.
30. L. J. Farrugia, J. Appl. Cryst., 1997, 30, 565.