Synthesis of fully substituted pyrazolo[3,4-b]pyridine-5-carboxamide derivatives via a one-pot four-component reaction

Tetrahedron Letters

Volumn 50, Issue 24, 2009, Pages 2911-2913

  Shaabani, Ahmad ^a   Seyyedhamzeh, Mozhdeh ^a   Maleki, Ali ^a   Behnam, Maryam ^a   Rezazadeh, Fahimeh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,3 Diphenyl 1H pyrazol 5 amine; Diketene; Multicomponent reaction; One pot; Pyrazolo 3,4 b pyridine 5 carboxamide

Indexed keywords

1,3 DIPHENYL 1H PYRAZOL 5 AMINE; 4 (4 CHLOROPHENYL) 6 METHYL 1,3 DIPHENYL N PROPYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; ALDEHYDE; ALIPHATIC AMINE; ALKENE DERIVATIVE; AMIDE; AROMATIC AMINE; DIKETENE; N (4 METHYLBENZYL) 4 (3 CHLOROPHENYL) 6 METHYL 1,3 DIPHENYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; N (4 METHYLBENZYL) 4 (4 BROMOPHENYL) 6 METHYL 1,3 DIPHENYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; N (4 METHYLBENZYL) 4 (4 FLUOROPHENYL) 6 METHYL 1,3 DIPHENYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; N (4 METHYLBENZYL) 6 METHYL 1,3 DIPHENYL 4 4 TOLYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; N BENZYL 4 (4 CHLOROPHENYL) 6 METHYL 1,3 DIPHENYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; N BENZYL 6 METHYL 1,3,4 TRIPHENYL 1H PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE; PYRAZOLO[3,4 B]PYRIDINE 5 CARBOXAMIDE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENVIRONMENTAL TEMPERATURE; MICHAEL ADDITION; ONE POT SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 65349196666     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.200     Document Type: Article

References (25)

1. Zhu J., and Bienayme H. Multicomponent Reactions (2005), Wiley-VCH, Weinheim
2. Dömling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
3. Hoehn, H.; Denzel, T. U.S. Patent 3,925,388, 1975, Chem. Abstr. 1976, 85, 21450s.
4. Meiners B.A., and Salama A.I. Eur. J. Pharmacol. 78 (1982) 315-322
5. Lynck B., Khan M., Teo H., and Pedrotti F. Can. J. Chem. 66 (1988) 420-428
6. Fujikama, Y.; Suzuki, M.; Iwasaki, H.; Sakashita, M.; Kitahara, M. Eur. Patent Appl., EP 339358, 1989, Chem Abstr. 1990, 113, 23903.
7. Chen, Y. L. Int. Patent WO9534563 A1, 1995, Chem. Abstr. 1995, 124, 232447.
8. Manetti F., Schenone S., Bondavalli F., Brullo C., Bruno O., Ranise A., Mosti L., Menozzi G., Fossa P., Trincavelli M.L., Martini C., Martinelli A., Tintori C., and Botta M. J. Med. Chem. 48 (2005) 7172-7185
9. Hamblin J.N., Angell T.D.R., Ballantine S.P., Cook C.M., Cooper A.W.J., Dawson J., Delves C.J., Jones P.S., Lindvall M., Lucas F.S., Mitchell C.J., Neu M.Y., Ranshaw L.E., Solanke Y.E., Somers D.O., and Wiseman J.O. Bioorg. Med. Chem. Lett. 18 (2008) 4237-4241
10. Witherington J., Bordas V., Gaiba A., Garton N.S., Naylor A., Rawlings A.D., Slingsby B.P., Smith D.G., Takle A.K., and Ward R.W. Bioorg. Med. Chem. Lett. 13 (2003) 3055-3057
11. Revesz L., Blum E., Di Padova F.E., Buhl T., Feifel R., Gram H., Hiestand P., Manning U., Neumann U., and Rucklin G. Bioorg. Med. Chem. Lett. 16 (2006) 262-266
12. Bharate S.B., Mahajan T.R., Gole Y.R., Nambiar M., Matan T.T., Kulkarni-Almeida A., Balachandran S., Junjappa H., Balakrishnan A., and Vishwakarma R.A. Bioorg. Med. Chem. 16 (2008) 7167-7176
13. Sagitullina G.P., Lisitskaya L.A., Vorontsova M.A., and Sagitullin R.S. Mendeleev Commun. 17 (2007) 192-193
14. Lavecchia G., Berteina-Raboin S., and Guillaumet G. Tetrahedron Lett. 45 (2004) 2389-2392
15. Quiroga J., Trilleras J., Insuasty B., Abonia R., Nogueras M., and Cobo J. Tetrahedron Lett. 49 (2008) 2689-2691
16. 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
17. Jachak M.N., Avhale A.B., Tantak C.D., and Toche R.B. J. Heterocycl. Chem. 42 (2005) 1311-1319
18. 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
19. Tu S., Wang Q., Zhang Y., Xu J., Zhang J., Zhu X., and Shi F. J. Heterocycl. Chem. 44 (2007) 811-814
20. Shaabani A., Maleki A., and Moghimi-Rad J. J. Org. Chem. 72 (2007) 6309-6311
21. Shaabani A., Maleki A., Mofakham H., and Moghimi-Rad J. J. Org. Chem. 73 (2008) 3925-3927
22. Shaabani A., Maleki A., Mofakham H., and Khavasi H.R. J. Comb. Chem. 10 (2008) 323-326
23. Shaabani A., Maleki A., and Mofakham H. J. Comb. Chem. 10 (2008) 595-598
24. Shaabani A., Maleki A., Mofakham H., and Khavasi H.R. J. Comb. Chem. 10 (2008) 883-885
25. 4O: C, 77.55; H, 5.17; N, 10.64. Found: C, 77.43; H, 5.01;