An efficient approach to heterocyclic analogues of xanthone: A short synthesis of all possible pyrido[5,6]pyrano[2,3-c]pyrazol-4(1H)-ones

Synthesis

Volumn , Issue 24, 2006, Pages 4219-4229

  Eller, Gernot A ^a   Wimmer, Veronika ^a   Haring, Andreas W ^a   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Acylations; Cyclizations; Fused ring systems; Nucleophilic aromatic substitutions; Pyrazolones

Indexed keywords

ACYLATIONS; CYCLIZATIONS; FUSED RING SYSTEMS; NUCLEOPHILIC AROMATIC SUBSTITUTIONS; PYRAZOLONES;

ACETIC ACID; CHLORINE COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KETONES;

1 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[2,3 B]PYRIDIN 4(1H) ONE; 1 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 4(1H) ONE; 1 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[2,3 C]PYRIDIN 4(1H) ONE; 1 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[3,2 B]PYRIDIN 4(1H) ONE; 1 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[3,2 C]PYRIDIN 4(1H) ONE; 1 BENZYL 3 METHYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]PYRIDIN 4(1H) ONE; 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]PYRIDIN 4(1H) ONE; 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 4(1H) ONE; 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[2,3 C]PYRIDIN 4(1H) ONE; 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[3,2 B]PYRIDIN 4(1H) ONE; 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[3,2 C]PYRIDIN 4(1H) ONE; 1,3 DIMETHYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]PYRIDIN 4(1H) ONE; 1,3 DIMETHYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 4(1H) ONE; 2 (4 METHOXYBENZYL)PYRAZOLO[4',3':5,6]PYRANO[3,2 C]PYRIDIN 4(2H) ONE; 3 CHLOROQUINOLINE 2 CARBONYL CHLORIDE; 3 METHYL 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 4(1H) ONE; 3 METHYL 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[2,3 C]PYRIDIN 4(1H) ONE; 3 METHYL 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[3,2 B]PYRIDIN 4(1H) ONE; 3 METHYL 1 PHENYLPYRAZOLO[4',3':5,6]PYRANO[3,2 C]PYRIDIN 4(1H) ONE; 4 (3 CHLOROISONICOTINOYL) 1H PYRAZOL 5 OL DERIVATIVE; CALCIUM HYDROXIDE; DIOXANE; HETEROCYCLIC COMPOUND; PHOSGENE; PYRAZOLO[4',3':5,6]PYRANO[2,3 C]PYRIDIN 4(1H) ONE DERIVATIVE; PYRAZOLONE; PYRIDO[5,6]PYRANO[2,3 C]PYRAZOL 4(1H) ONE DERIVATIVE; QUINOLINE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ACYLATION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 33845988041     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950324     Document Type: Article

References (26)

1. (a) Fotie, J.; Bohle, D. S. Anti-Infect. Agents Med. Chem. 2006, 5, 15.
2. (b) Pinto, M. M. M.; Sousa, M. E.; Nascimento, M. S. J. Curr. Med. Chem. 2005, 12, 2517.
3. Peres, V.; Nagem, T. J.; de Oliveira, F. F. Phytochemistry 2000, 55, 683.
4. Bell, J. Clin. Drug Invest. 2005, 25, 555.
5. (a) Chantegrel, B.; Nadi, A. I.; Gelin, S. Synthesis 1983, 214.
6. (b) Eiden, F.; Rademacher, G. Arch. Pharm. (Weinheim, Ger.) 1983, 316, 34.
7. (c) Mitsubishi Petrochemical Co. Ltd.; JP 57158787, 1982; Chem. Abstr. 1983, 98, 143408.
8. (d) Catarzi, D.; Cecchi, L.; Colotta, V.; Filacchioni, G.; Martini, C.; Tacchi, P.; Lucacchini, A. J. Med. Chem. 1995, 38, 1330.
9. (e) Sarenko, A. S.; Kvitko, I. Ya.; Éfros, L. S. Chem. Heterocycl. Compd. (Engl. Transl.) 1972, 8, 722;
10. Khim. Geterotsikl. Soedin. 1972, 799.
11. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The Tautomerism of Heterocycles, In Advances in Heterocyclic Chemistry, 1st Suppl.; Academic Press: New York, 1976, 656;
12. Chem. Abstr. 1976, 85, 93699.
13. Jensen, B. S. Acta Chem. Scand. 1959, 13, 1668.
14. Eller, G. A.; Holzer, W. Heterocycles 2004, 63, 2537.
15. Becker, W.; Eller, G. A.; Holzer, W. Synthesis 2005, 2583.
16. Holzer, W.; Kautsch, C.; Laggner, C.; Claramunt, R. M.; Pérez-Torralba, M.; Alkorta, I.; Elguero, J. Tetrahedron 2004, 60, 6791.
17. (a) Braun, S.; Kalinowski, H.-O.; Berger, S. A Practical Course, In 150 and More Basic NMR Experiments, 2nd Ed.; Wiley-VCH: Weinheim, 1999, 596;
18. Chem. Abstr. 1999, 131, 184497.
19. (b) Jippo, T.; Kamo, O.; Nagayama, N. J. Magn. Reson. 1986, 66, 344.
20. Michaelis, A. Justus Liebigs Ann. Chem. 1911, 385, 1.
21. Holzer, W.; Krca, I. Heterocycles 2003, 60, 2323.
22. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Quéguiner, G.; Siddiqui, M. A.; Snieckus, V. J. Org. Chem. 1995, 60, 292.
23. Rao, K. R.; Bhanumathi, N.; Sattur, P. B. J. Heterocycl. Chem. 1991, 28, 1339.
24. Barrière, J.-C.; Bacqué, E.; Puchault, G.; Quenet, Y.; Molherat, C.; Cassayre, J.; Paris, J.-M. Tetrahedron 1998, 54, 12859.
25. Marzi, E.; Bobbio, C.; Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2005, 2116.
26. Cziaky, Z. Synth. Commun. 1991, 21, 1929.