Condensation of 2-pyrone with 3-aminopyrazolone. A novel synthesis of pyrazolo[3,4-b]pyridines

Synthetic Communications

Volumn 34, Issue 12, 2004, Pages 2195-2204

  Fadel, S ^a   Hajbi, Y ^a   Rakib, E M ^a   Khouili, M ^a   Pujol, M D ^b   Guillaumet, G ^c  

^a SULTAN MOULAY SLIMANE UNIVERSITY   (Morocco)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

Decarboxylation; Esterification; N Butanol; Pyrazolo 3,4 b pyridines; Pyrones

Indexed keywords

2 PYRONE DERIVATIVE; 3 AMINOPYRAZOLONE; HETEROCYCLIC COMPOUND; PYRAZOLO[3,4 B]PYRIDINE DERIVATIVE; PYRAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; ESTERIFICATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 3142676344     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120038500     Document Type: Article

References (19)

1. Hoehn, H.; Denzel, T. 1H-Pyrazolo[3,4-b]pyridine. Ger. Offen. US Patent 3,755,340, 1973; 25.
2. Meiners, B.A.; Salama, A.I. Enhancement of benzodiazepine and GABA binding by the novel anxiolytic, tracazolate. Eur. J. Pharmacol. 1982, 78 (3), 315-322.
3. Lynch, B.M.; Khan, M.A.; Teo, H.C.; Pedrotti, F. Pyrazolo[3,4-b] pyridines: syntheses, reactions, and nuclear magnetic resonance spectra. Can. J. Chem. 1988, 66 (3), 420-428.
4. Guixue, Y.; Helen, J.M.; Ximao, W.; Jian, W.; Saeho, C.; Gary, D.; Andrew, H.; Ronald, P.; Laurie, S.; Bin, H.; Diane, N.; Leonard, A.; John, K.; John, E.M. Substituted pyrazolopyridines as potent and selective PDE5 inhibitors: potential agents for treatment of erectile dysfunction. J. Med. Chem. 2001, 44, 1025-1027.
5. El-Dean, A.M.; Aralla, A.A.; Mohamed, T.A.; Geies, A.A. Synthesis of some pyrazolopyridinesulfonamide derivatives. Z. Naturforsch. Teil B: Chem. Sci. 1991, 46 (4), 541-546.
6. Fujikama, Y.; Suzuki, M.; Iwasaki, H.; Sakashita, M.; Kitahara, M. Preparation and formulation of pyrazolopyridine-type mevalonolactones as antihyperlipidemics. Eur. Pat. Appl. EP339,358, 1989; 71.
7. Abdel Hafed, A.; Awad, I.M.A.; Ahmed, R.A. New heterocyclic substituted pyrazolo[3,4-b]pyridine derivatives. Collect. Czech. Chem. Commun. 1993, 58 (5), 1198-1202.
8. Hardy, C.R. The chemistry of pyrazolopyridines. Adv. Heterocycl. Chem. 1984, 36, 343-409.
9. Molina, P.; Arques, A.; Fresneda, P.M.; Vinader, M.V.; Foces-Foces, M.C.; Hernandez Cano, F. Heterocyclization reactions of conjugated heterocumulenes. Synthesis of pyridine derivatives by a tandem aza-Wittig/electrocyclization strategy. Chem. Ber. 1989, 122 (2), 307-313.
10. Benoit, R.; Dupas, G.; Bourguignon, J.; Quéguiner, G. Facile synthesis of annelated NADH model precursors. Synthesis 1987, (12), 1124-1126.
11. Bare, T.M.; McLaren, C.D.; Campbell, J.B.; Firor, J.W.; Resch, J.F.; Walters, C.P.; Salama, A.I.; Meiners, B.A.; Patel, J.B. Synthesis and structure-activity relationships of a series of anxioselective pyrazolo-pyridine ester and amide anxiolytic agents. J. Med. Chem. 1989, 32 (12), 2561-2573.
12. Sanghvi, Y.S.; Larson, S.B.; Robins, R.K.; Revankar, G.R. A convenient synthesis of pyrazolo[3,4-b]pyridine nucleosides by convenient ring-closure procedures. X-ray crystal and molecular structure of 4-amino-1-(α-D- ribofuranoyl)-1,7-dihydropyrazolo[3,4-b]pyridin-6-one. J. Chem. Soc., Perkin Trans. I 1990, (11), 2943-2950.
13. El Abbassi, M.; Essassi, E.M.; Fifani, J. New synthesis of 1,5-benzodiazepines from γ-pyrones. Tetrahedron Lett. 1987, 28 (13), 1389-1392.
14. El Abbassi, M.; Essassi, E.M.; Fifani, J. Dehydroacetic acid. Precursor in the synthesis of benzodiazepines. Tetrahedron Lett. 1989, 30 (50), 7069-7070.
15. Maàmr, H.; Grech, O.; Sakellariou, R.; Spèziale, V. New method of synthesis of 1,5-benzodiazepin-2-ones from 4-hydroxycoumarin. J. Heterocycl. Chem. 1994, 31 (2), 509-511.
16. Maàmr, H.; Cottet, S.; Tedeschi, C.; Spèziale, V. Reaction of 1,2-diamines with 4-hydroxycoumarin. Synthesis of 1,4-diazepin-5-ones. J. Heterocycl. Chem. 1997, 34 (6), 1821-1824.
17. El Abbassi, M.; Essassi, E.M.; Fifani, J. Synthesis of new 4-acetonylidene-1,5-benzodiazepin-2-ones III. Condensation of monosubstituted o-phenylenediamine with γ-pyrone. Bull. Soc. Chim. Belg. 1997, 106 (4), 205-210.
18. El Kihel, A.; Benchidmi, M.; Essassi, E.M.; Danion-Bougot, R. Reaction of aminobenzimidazoles with 4-hydroxy-6-methyl-2-pyrone and 4-hydroxycoumarin. Synth. Commun. 1999, 29 (14), 2435-2445.
19. Rakib, E.M.; Benchidmi, M.; Essassi, E.M.; El Bouadili, A.; Khouili, M.; Mark, V.; Pujol, M.D. Reactivity of 7-aminoindazole as a bidendate nucleophile. Heterocycles 2000, 53 (12), 2617-2627.