Synthesis of 4-aryl-3-methyl-6-oxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-5-carbonitrile via a one-pot, three-component reaction

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2967-2970

  Rahmati, Abbas ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYL 6 OXO 4 PARA TOLYL 4,5,6,7 TETRAHYDRO 2H PYRAZOLO[3,4 B]PYRIDINE 5 CARBONITRILE; 4 (4 METHOXYPHENYL) 3 METHYL OXO 4,5,6,7 TETRAHYDRO 2H PYRAZOLO[3,4 B]PYRIDINE 5 CARBONITRILE; 4 ARYL 3 METHYL 6 OXO 4,5,6,7 TETRAHYDRO 2H PYRAZOLO[3,4 B]PYRIDINE 5 CARBONITRILE DERIVATIVE; 4 TOLUENE SULFONIC ACID; CHEMICAL COMPOUND; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; IRRADIATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77951253882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.109     Document Type: Article

References (28)

1. Kappe C.O. Curr. Opin. Chem. Biol. 6 (2002) 314-320
2. Domling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
3. In: Zhu J., and Bienayme H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
4. Straub A.S., and Alonso-Alija J.P.C. Bioorg. Med. Chem. Lett. 11 (2001) 781
5. Elnagdi M.N., Elmoghayar M.R.H., and Elgemeie G.E.H. Adv. Heterocycl. Chem. 41 (1987) 320
6. Kuribayashi S., Goto K., Naito S., Kamataki T., and Yamazaki H. Chem. Res. Toxicol. 22 (2009) 323-331
7. Lynck B., Khan M., Teo H., and Pedrotti F. Can. J. Chem. 66 (1988) 420-428
8. Gopalsamy A., Ciszewski G., Hu Y., Lee F., Feldberg L., Frommer E., Kim S., Collins K., Wojciechowicz D., and Mallon R. Bioorg. Med. Chem. Lett. 19 (2009) 2735-2738
9. Mukaiyama H., Nishimura T., Kobayashi S., and Komatsu Y. Bioorg. Med. Chem. 16 (2008) 909-921
10. Huang S., Lin R., Yu Y., Lu Y., Connolly P., Chiu G., Li S., Emanuel S., and Middleton S. Bioorg. Med. Chem. Lett. 17 (2007) 1243-1245
11. Saggar, S.; Sisko, J.; Tucker, T.; Tynebor, R.; Su, D.; Anthony, N. U.S. Patent Appl. US 2007,021,442, 2007; Chem. Abstr. 2007, 146, 163149.
12. Wang Y.D., Honores E., Wu B., Johnson S., Powell D., Miranda M., McGinnis J.P., Discafani C., Rabindran S.K., Cheng W., and Krishnamurthy G. Bioorg. Med. Chem. 17 (2009) 2091-2100
13. Ahmed O.M., Mohamed M.A., Ahmed R.R., and Ahmed S.A. Eur. J. Med. Chem. 44 (2009) 3519-3523
14. Hoehn, H.; Denzel, T. U.S. Patent 3925,388, 1975; Chem. Abstr. 1976, 85, 21450s.
15. Meiners B.A., and Salama A.I. Eur. J. Pharmacol. 78 (1982) 315-322
16. Chen, Y. L. Int. Patent WO9534563 A1, 1995; Chem. Abstr. 1995, 124, 232447.
17. Sagitullina G.P., Lisitskaya L.A., Vorontsova M.A., and Sagitullin R.S. Mendeleev Commun. 17 (2007) 192-193
18. Lavecchia G., Berteina-Raboin S., and Guillaumet G. Tetrahedron Lett. 45 (2004) 2389-2392
19. Quiroga J., Trilleras J., Insuasty B., Abonia R., Nogueras M., and Cobo J. Tetrahedron Lett. 49 (2008) 2689-2691
20. Chebanov V.A., Saraev V.E., Desenko S.M., Chernenko V.N., Knyazeva I.V., Groth U., Glasnov T.N., and Kappe C.O. J. Org. Chem. 73 (2008) 5110-5118
21. Jachak M.N., Avhale A.B., Tantak C.D., and Toche R.B. J. Heterocycl. Chem. 42 (2005) 1311-1319
22. Diaz-Ortiz A., Carrillo J.R., Cossio F.P., Gomez-Escalonilla M.J., de la Hoz A., Moreno A., and Prieto P. Tetrahedron 56 (2000) 1569-1577
23. Tu S., Wang Q., Zhang Y., Xu J., Zhang J., Zhu X., and Shi F. J. Heterocycl. Chem. 44 (2007) 811-814
24. Shaabani A., Rahmati A., Rezayan A.H., Darvishi M., Badri Z., and Sarvari A. QSAR Comb. Sci. 26 (2007) 973-979
25. Shaabani A., Rahmati A., and Naderi S. Bioorg. Med. Chem. Lett. 15 (2005) 5553-5557
26. Shaabani A., Farhangi E., and Rahmati A. Comb. Chem. High Throughput Screening 9 (2006) 771-776
27. Shaabani A., Rahmati A., and Farhangi E. Tetrahedron Lett. 48 (2007) 7291-7294
28. 2O (2 × 20 ml). The solid product recrystallized slowly from EtOH after 1-2 d.