Quinoxalines XV. convenient synthesis and structural study of pyrazolo[1,5-a]quinoxalines

Journal of Organic Chemistry

Volumn 74, Issue 3, 2009, Pages 1282-1287

  Sarodnick, Gerhard ^a,b   Linker, Torsten ^a,b   Heydenreich, Matthias ^a,c   Koch, Andreas ^a,c   Starke, Ines ^a,c   Fürstenberg, Sylvia ^a,c   Kleinpeter, Erich ^a,c  

^a UNIVERSITY OF POTSDAM   (Germany)

^b Organische Chemie   (Germany)

^c Analytische Chemie   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDES; COLLISION-INDUCED DISSOCIATIONS; DFT CALCULATIONS; FRAGMENTATION PATTERNS; GAS-PHASE; HIGH TEMPERATURES; INTRAMOLECULAR HYDROGEN BONDINGS; NMR SPECTROSCOPIES; ONE STEPS; PHENOL DERIVATIVES; QUINOXALINES; REARRANGEMENT PROCESS; SIGMATROPIC REARRANGEMENTS; STRUCTURAL STUDIES;

ALDEHYDES; HYDROGEN; HYDROGEN BONDS; MAGNETIC PROPERTIES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; POTASSIUM; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

POTASSIUM HYDROXIDE;

ACETIC ANHYDRIDE; ALDEHYDE DERIVATIVE; ARYLOXYMETHYLQUINOXALINE OXIME DERIVATIVE; PHENOL DERIVATIVE; POTASSIUM HYDROXIDE; PYRAZOLO[1,5 A]QUINOXALINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DISSOCIATION; ELIMINATION REACTION; HIGH TEMPERATURE; HYDROGEN BOND; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SAPONIFICATION;

HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRAZOLES; QUINOXALINES; THERMODYNAMICS;

EID: 64549144672     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802398g     Document Type: Article

References (34)

1. (a) Chemistry of Heterocyclic Compounds; Springer: New York, 2008; Vol. 44.
2. (b) Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Elsevier: London, 2008; Vol. 96.
3. Aulenta, F.; Wefelscheid, U. K.; Brüdgam, I.; Reissig, H.-U. Eur. J. Org. Chem. 2008, 2325-2335.
4. (a) Kim, H. S.; Chung, J. Y.; Kim, E. K.; Park, Y. T.; Hong, Y. S.; Lee, M. K.; Kurasawa, Y.; Takada, A. J. Heterocycl. Chem. 1996, 33, 1855-1858.
5. (b) Makino, K.; Kim, H. S.; Kurasawa, Y. J. Heterocycl. Chem. 1999, 36, 321-328.
6. (c) Sarodnick, G.; Linker, T. J. Heterocycl. Chem. 2001, 38, 829-836.
7. (d) Sarodnick, G.; Heydenreich, M.; Linker, T.; Kleinpeter, E. Tetrahedron 2003, 59, 6311-6321.
8. (e) Heydenreich, M.; Koch, A.; Sarodnick, G.; Kleinpeter, E. Tetrahedron 2005, 61, 2373-2385.
9. (f) El Ashry, E. S. H.; Atta, K. F.; Aboul-Ela, S.; Beldi, R. J. Carbohydr. Chem. 2007, 26, 1-16.
10. (a) Albini, A.; Bettinetti, G.; Minoli, G. J. Chem. Soc., Perkin Trans. 1 1983, 2491-2494.
11. (b) Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc. 1997, 119, 7308-7315.
12. (c) Albini, A.; Bettinetti, G.; Minoli, G. J. Am. Chem. Soc. 1999, 121, 3104-3113.
13. (d) Carra, C.; Bally, T.; Albini, A. J. Am. Chem. Soc. 2005, 127, 5552-5562.
14. (a) Wai, J. S.; Williams, P. D.; Langford, H. M. PCT Int. Appl. WO 2005120516, 2005; Chem. Abstr. 2005, 1328397.
15. (b) Moarbess, G.; Deleuze-Masquefa, C.; Bonnard, V.; Gayraud-Paniagua, S.; Vidal, J.-R.; Bressolle, F.; Pinguet, F.; Bonnet, P.-A. Bioorg. Med. Chem. 2008, 16, 6601-6610.
16. Starke, I.; Sarodnick, G.; Ovcharenko, V. V.; Pihlaja, K.; Kleinpeter, E. Tetrahedron 2004, 60, 6063-6078.
17. Review: Gawley, R. E. Org. React. 1988, 35, 1-420.
18. Review: (a) Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 21, 4505-4519. Very recent example:
19. (b) Counceller, C. M.; Eichmann, C. C.; Wray, B. C.; Stambuli, J. P Org. Lett. 2008, 10, 1021-1023.
20. Fusco, R.; Sannicolo, F. J. Org. Chem. 1981, 46, 83-89.
21. Malatesta, V.; Neri, C.; Wis, M. L.; Montanari, L.; Millini, R. J. Am. Chem. Soc. 1997, 119, 3451-3455.
22. Foresman, J. B.; Keith, A. T.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 160098-161104.
23. Kleinpeter, E.; Klod, S.; Koch, A. J. Mol. Struct. (THEOCHEM) 2007, 811, 45-60, and references therein.
24. Klod, S.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2001, 1893-1898.
25. Ditchfield, R. Mol. Phys. 1974, 27, 789-807.
26. Porter, Q. N. Mass Spectrometry of Heterocyclic Compounds, 2nd ed.; John Wiley: New York, 1985.
27. Kingston, E. E.; Beynon, J. H.; Liehr, J. G.; Meyrant, P.; Flammang, R.; Maquestiau, A. Org. Mass Spectrom. 1985, 20, 351-359.
28. Ramana, D. V.; Sudha, M. S. J. Chem. Soc., Perkin Trans. 2 1993, 675-678.
29. Eichinger, P. C. H.; Bowie, J. H.; Hayes, R. N. J. Org. Chem. 1987, 52, 5224-5228.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
32. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785-789.
33. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
34. SYBYL 7.3; Tripos Inc.: 1699 South Hanley Road, St. Louis, MO 63144.