Advances in the Synthesis of Pyrazolo[3,4-b]pyridines

Current Organic Chemistry

Volumn 16, Issue 3, 2012, Pages 400-417

  Dodiya, Dipti K ^a   Trivedi, Amit R ^a   Kataria, Vipul B ^a   Shah, Viresh H ^a  

^a SAURASHTRA UNIVERSITY   (India)

Author keywords

1,3 dicarbonyl synthons; 3 cyanopyridines; Aminopyrazoles; Pyrazolo 3,4 b pyridines; Ring opening reactions; Synthesis of pyrazolo 3,4 b pyridines

Indexed keywords

1,3-DICARBONYL SYNTHON; 3-CYANOPYRIDINE; AMINOPYRAZOLE; DICARBONYLS; LATEST DEVELOPMENT; PYRAZOLO[3,4-B]PYRIDINE; RING CLOSINGS; RING OPENING REACTION; SYNTHESIS OF PYRAZOLO[3,4-B]PYRIDINE; SYNTHONS;

EID: 84857733135     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212799499912     Document Type: Review

References (112)

1. Dias, L.R.S.; Alvim, M.J.; Freitas, A.C.; Barreiro, E.J.; Miranda A.L.P. Synthesis and analgesic properties of 5-acyl-arylhydrazone 1-H pyrazolo [3,4-b] pyridine derivatives. Pharm. Acta Helv., 1994, 69(3), 163-169.
2. Falco, J.L.; Lloveras, M.; Buira, I.; Teixido, J.; Borrell, J.I. Design, synthesis and biological activity of acyl substituted 3-amino-5-methyl- 1,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones as potential hypnotic drugs. Eur. J. Med. Chem., 2005, 40, 1179-1187.
3. Mendez, E., Terencio, J.; Palomer, A.; Antonio GugliettaLynck, B.; Khan, M.; Teo, H.; Pedrotti, F. Can. J. Chem., 1988, 66, 420-428.
4. Bernardino, A.M.R.; Azevedo, A.R.; Pinheiro, L.C.S.; Borges, J.C.; Carvalho, V.L.; Miranda, M.D.; Meneses, M.D.F.; Nascimento, M.; Ferreira, D.; Rebello, M.A.; Silva, V.A.G; Frugulhetti, I.C. Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1Hpyrazolo[ 3,4-b]pyridine-4-carboxylic acids derivatives. Med. Chem. Res., 2007, 16, 7-9.
5. Tucker, T.J.; Sisko, J.T.; Tynebor, R.M.; Williams, T.M.; Felock, P.J.; Flynn, J.A.; Lai, M.-T.; Liang, Y.; McGaughey, G.; Liu, M.; Miller, M.; Moyer, G.; Munshi, V.; Perlow-Poehnelt, R.; Prasad, S.; Reid, J.C.; Sanchez, R.; Torrent, M.; Vacca, J.P.; Wan, B.-L.; Yan, Y. Discovery of 3-{5-[(6-Amino-1Hpyrazolo[ 3,4-b]pyridine-3-yl)methoxy]-2-chlorophenoxy}-5- chlorobenzonitrile (MK-4965): a potent, orally bioavailable HIV-1 nonnucleoside reverse transcriptase inhibitor with improved potency against key mutant viruses. J. Med. Chem., 2008, 51, 6503-6511.
6. Chen, Y. L. Pyrazolopyridines useful as CRF antagonists. WO 9534563 A1 1995, Chem. Abstr. 1995, 124, 232447.
7. 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.; Botta, M. Synthesis and 3D QSAR of new pyrazolo[3,4-b]pyridines: potent and selective inhibitors of A1 Adenosine Receptors. J. Med. Chem., 2005, 48(23), 7172-7185.
8. 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.; Wiseman, J. O. Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors. Bioorg. Med. Chem. Lett., 2008, 18, 4237-4241.
9. Misra, R.N.; Xiao, H.; Rawlins, D.B.; Shan, W.; Kellar, K.A.; Mulheron, J.G.; Sack, J.S.; Tokarski, J.S.; Kimbally, D.; Webster, K.R. 1HPyrazolo[ 3,4-b]pyridine inhibitors of cyclin-dependent kinases: highly potent 2,6-difluorophenacyl analogues. Bioorg. Med. Chem. Lett., 2003, 13, 2405-2408.
10. Witherington, J.; Bordas, V.; Gaiba, A.; Garton, N.S.; Naylor, A.; Rawlings, A. D.; Slingsby, B. P.; Smith, D. G.; Takle, A. K.; Ward, R. W. 6-Arylpyrazolo[ 3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3). Bioorg. Med. Chem. Lett., 2003, 13(18), 3055-3057.
11. Sharma, P.K.; Singh, K.; Kumar, S.; Kumar, P.; Dhawan, S.N.; Lal, S.; Ulbrich, H.; Dannhardt, G. Synthesis and anti-inflammatory evaluation ofsome pyrazolo[3,4-b]pyridines. Med. Chem. Res., 2010, 19, 107-114.
12. Bharate, S.B.; Mahajan, T.R.; Gole, Y.R.; Nambiar, M.; Matan, T.T.; Kulkarni- Almeida, A.; Balachandran, S.; Junjappa, H.; Balakrishnan, A.; Vishwakarma, R.A. Synthesis and evaluation of pyrazolo[3,4-b]pyridines and itsstructural analogues as TNFand IL-6 inhibitors. Bioorg. Med. Chem., 2008, 16, 7167-7176.
13. Hardy, C.R. Advances in Heterocyclic Chemistry; Alan R. Katritzky, Ed.; Elsevier Science B. V: Amsterdam, 1984; Vol. 36, pp. 343-409.
14. Orlov, V.D.; Quiroga, J.; Kolos, N.N. Synthesis of aromatic derivatives of pyrazolo[4,5-b]pyridine. Khim. Geterosikl. Soedin., 1987, 9, 1247-1251.
15. Joshi, K.C.; Pathak, V.N.; Sareen, V.; Garg, U. Synthesis of some new fluorine containing 1H-pyrazolo[3,4-b]pyridines. J. Ind. Chem. Soc., 1987,64, 372-3.
16. Cocco, M.T.; Congiu, C.; Onnis, V. Synthesis of 2H-pyrazolo[3,4-b]pyridin- 3-ols via cyclization of pyrazoleacrylonitriles. J. Heterocycl. Chem., 1994, 31, 925-928.
17. Al-Mousawi, S.M.; Kaul, K.; Mohammad, M.A.; Elnagdi, M.H. Studies with Condensed Azines: New routes to pyrazolo[3,4-b]pyridines and pyrrolo[3,2- b]pyridines. J. Chem. Res. (S), 1997, 9, 318-319.
18. Quiroga, J.; Alvarado, M.; Insuasty, B.; Moreno, R.; Ravina, E.; Estevez, I.; De Almeida, R. H. Synthesis of 5-cyanopyrazolo[3,4-b]pyridines in the reaction of 5-amino-3-methyl-1-phenylpyrazole with arylidene derivatives ofmalonodinitrile and ethyl cyanoacetate. J. Heterocycl. Chem., 1999, 36, 1311-1316.
19. Elagamey, A.G.A.; El-Taweal, F.M.A.; Amer, F.A.K. α,β-unsaturated nitriles in heterocyclic synthesis. II. Synthesis of pyrazolo[3,4-b]pyridine and pyrazolo[1,5-a]pyrimidine derivatives of antipyrine. J. Prakt. Chem., 1987,329, 469-473.
20. Youssef, A.M.S. New synthesis of pyrazolo[3,4-b]pyridines. Egypt. J. Chem., 1999, 42, 293-300.
21. Chebanov, V.A.; Sakhno, Y.I.; Desenko, S.M.; Chernenko, V.N.; Musatov, V.I.; Shishkina, S.V.; Shishkin O. V.; Kappe, C. O. Cyclocondensation reactions of 5-aminopyrazole, pyruvic acids and aldehydes. Multi-component approachesto pyrazolopyridines and related products. Tetrahedron, 2007, 63, 1229-1242.
22. Quiroga, J.; Hormaza, A.; Insuasty, B.; Marquez, M. Reaction of 5-amino-1- aryl-3-methylpyrazoles with benzylidene derivatives of Meldrum's acid: synthesisand characterization of pyrazolo[3,4-b]pyridinones. J. Heterocycl. Chem., 1998, 35, 409-412.
23. Lipson, V.V.; Karnozhitskaya, T.M.; Desenko, S.M.; Shishkina, S.V.; Shishkin, O.E.; Musatov, V.I. Reactions of α-Aminoazoles with diethyl benzylidenemalonate. Russ. J. Org. Chem., 2007, 43, 249.
24. Erian, A.W.; El-Gohary, S.; Manhi, F.M.; Ali, F.A. A novel synthesis of fused pyrazole systems as antimicrobial agents. Pharmazie, 1998, 53, 748-751.
25. El-Emary, T.I. Synthesis of newly substituted pyrazoles and substituted pyrazolo[3,4-b]pyridines based on 5-amino-3-methyl-1-phenylpyrazole. J.Chinese Chem. Soc., 2007, 54, 507-518.
26. Takahashi, M.; Nagaoka, H.; Inoue, K. Synthesis of trifluoromethylated pyrido[2,3-d]pyrimidine-2,4-diones from 6-aminouracils and trifluoromethylated pyrazolo[3,4-b]pyridines from 5-aminopyrazoles. J. Heterocycl. Chem., 2004, 41, 525-530.
27. Abdel-Aziz, H.A.; Saleh, T.S.; El-Zahabi, H.- S.A Facile Synthesis and invitro antitumor activity of some pyrazolo[3,4-b]pyridines and pyrazolo[1,5- a]pyrimidines linked to a thiazolo[3,2-a]benzimidazole moiety. Arch. Pharm., 2009, 343, 24-30.
28. Zou, X.; Tu, S.; Shi, F.; Xu, J. An efficient synthesis of pyrazolo[3,4- b]pyridine derivatives under microwave irradiation. Arkivoc, 2006, 2, 130-135.
29. Zou, X.; Tu, S.-J.; Zhu, S.-L.; Ji, S.-J.; Zhang, Y. Synthesis and crystal structure of 1-phenyl-3-methyl-4-(4-bromophenyl)-6-(2-chlorophenyl)pyrazolo[3,4-b]pyridine under microwave irradiation. Chinese J. Struc. Chem., 2005, 24, 109-113.
30. Shia, D.-Q.; Shi, J.-W.; Yao, H.; Jiang, H.; Wang, X.-S. An efficient Synthesis of pyrazolo[3,4-b]pyridine derivatives in aqueous media. J. Chinese Chem. Soc., 2007, 54, 1341-1345.
31. Quiroga, J; Trilleras, J; Sanchez, A.I; Insuasty, B; Abonia, R; Nogueras, M; Cobo, J. Regioselective three-component synthesis of indolylpyrazolo[3,4- b]pyridines induced by microwave and under solvent-free conditions. J. Heterocycl. Chem., 2007, 44, 1013-1017.
32. Shi, D.-Q.; Yao H.; Shi, J.-W. Three-Component, one-pot synthesis of pyrazolo[ 3,4-b]pyridine derivatives in aqueous media. Synth. Commun., 2008, 38, 1662-1669.
33. Tu, S.; Jia, R.; Zhang, J. Synthesis of novel substituted Pyrazolo[3,4- b]pyridines. J. Chinese Chem. Soc., 1999, 46, 333-336.
34. Lipson, V.V.; Borodina, V.V.; Shirobokova, M.G.; Desenko, S.M.; Shishkin, O.V.; Zubatyuk, R.I. Interaction of aminoazoles with Meldrum's acid and dialkyl ketones or cyclohexanone. Chem. Heterocycl. Comp., 2007, 43, 490-495.
35. Zhang, X.Y.; Li, X.Y.; Fan, X.S.; Wang, X.; Wang, J.J.; Qu, G.R. A novel synthesis of pyrazolo[3,4-b]pyridine derivatives through multi-component reaction in ionic liquid. Chinese Chem. Lett., 2008, 19, 153-156.
36. Rahmati, A. α Synthesis of 4-aryl-3-methyl-6-oxo-4,5,6,7-tetrahydro-2Hpyrazolo[ 3,4-b]-pyridine-5-carbonitrile via a one-pot, three-component reaction. Tetrahedron Lett., 2010, 51, 2967-2970.
37. Abu, Almaati, T.M.; El-Taweel, F.M. New trends in the chemistry of 5- aminopyrazoles. J. Heterocycl. Chem., 2004, 41, p. 109-34.
38. Popilnichenko, S.V.; Pilo, S.G.; Brovarets, B.S.; Chernega, A.N.; Drach, B.S. Synthesis of 3(5)-Amino-4-acylamino-5(3)-arylsulfanylpyrazoles and their fused derivatives on the basis of N-(2,2,2-Trichloro-1- hydroxyethyl)benzamides. Russ. J. Gen. Chem., 2005, 75, 1816-1820
39. Abdelhamid, A.O.; Baghos, V.B.; Halim, M. M.A. Synthesis and reactivity of N-[3-amino-4-(benzoxazol-2-yl)pyrazol-5-yl]phenylamine. J. Chem. Res. (S), 2007, 7, 420-425.
40. Badgujar, N.S.; Yewalkar, N.N.; Jachak, M N. In: International Electronic Conference on Synthetic Organic Chemistry, Proceedings of ECSOC-9, Basel, Switzerland, Nov. 1-30, 2005; Seijas, Julio A.; Vazquez Tato, M. Pilar, Eds.; Molecular Diversity Preservation International: Basel, Switzerland, 2005; pp. 5-8.
41. Nam, N.L.; Grandberg, I.I.; Sorokin, V.I. Condensation of 1-substituted 5- aminopyrazoles with β-dicarbonyl compounds. Chem. Heterocycl. Comp., 2003, 39, 937-942.
42. 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, 420-428.
43. Dias, R.S.; Freitas, A.C.C.; Barreiro, E.J.; Goins, D.K.; Nanayakkara, D.; McChesney, J.D. Synthesis and biological activity of new potential antimalarials: 1H-pyrazolo[3,4-b]pyridine derivatives. Boll. Chim. Farm., 2000, 139, 14-19.
44. Rivkin, A.; Adams, B. Solvent-free microwave synthesis of 4-hydroxy-3- phenylquinolin-2(1H)-ones and variants using activated arylmalonates. TetrahedronLett. 2006, 47, 2395-2398.
45. Takahashi, M.; Nagaoka, H.; Inoue, K. Synthesis of trifluoromethylated pyrido[2,3-d]pyrimidine-2,4-diones from 6-aminouracils and trifluoromethylatedpyrazolo[3,4-b]-pyridines from 5-aminopyrazoles. J. Heterocycl. Chem., 2004, 41, 525-530.
46. Volochnyuk, D.M.; Pushechnikov, A.O.; Krotko, D.G.; Sibgatulin, D.A.; Kovalyova, S.A.; Tolmachev, A. A. Electron-rich amino heterocycles for regiospecificsynthesis of trifluoromethyl-containing fused pyridines. Synthesis, 2003, 10, 1531-1540.
47. Singh, S.P.; Naithani, R.; Aggarwal, R.; Om Prakash. Synthesis of some novel fluorinated pyrazolo[3,4-b]pyridines. Synth. Commun., 2004, 34, 4359-4367.
48. Emelina, E.E.; Petrov, A.A.; Selivanov, S.I.; Filyukov, D.V. α-Aminoazoles in synthesis of heterocycles- III: 4-trifluoromethylpyrazolo[3,4-b]pyridines: synthesis and structure. Russ. J. Org. Chem., 2008, 44, 251-256.
49. Petrov, A.A.; Emelina, E.E.; Selivanov, S.I. α-Aminoazoles in synthesis of heterocycles- IV: regiodirection of 3(5)-amino-5(3)-methylpyrazole reaction with hexafluoroacetylacetone. Russ. J. Org. Chem., 2008, 44, 269-275.
50. Solodukhin, S.Y.; Peregudov, A.S.; Vorontsov, E.V.; Chkanikov, N.D. Phenoxydifluoromethyl substituted nitrogen heterocycles. synthesis and heterocyclization reactions of ethyl 4,4-difluoro-4-phenoxyacetoacetate. Molecules, 2004, 9, 164-169.
51. Zhu, S.-L.; Ji, S.-J.; Zhao, K.; Liu, Y. Multicomponent reactions for thesynthesis of new 3'-indolyl substituted heterocycles under microwave irradiation. Tetrahedron Lett., 2008, 49, 2578-2582.
52. Jachak, M.N.; Avhale, A.B.; Ghotekar, B.K.; Kendre, D.B.; Toche, R.B. Synthesis of pyrazolo[3,4-b]pyridines using ammonium acetate as green reagent in multi-component reactions. J. Heterocycl. Chem., 2008, 45, 1221-1224.
53. Quiroga, J.; Cruz, S.; Insuasty, B.; Abonia, R. Synthesis of 5-cyano-4,7- dihydropyrazolo[3,4-b]pyridin-4-ones and 5-cyanopyrazolo[3,4-b]pyridin-4-ones in one-step by the reaction of 5-aminopyrazolone with benzaldehyde and benzoylacetonitrile in ethanol and by microwave radiation in dry media. Heterocycl. Commun., 2000, 6, 275-282.
54. Shaabani, A.; Seyyedhamzeh, M.; Maleki, A.; Behnam, M.; Rezazadeh, F. Synthesis of fully substituted pyrazolo[3,4-b]pyridine-5-carboxamide derivativesvia a one-pot four-component reaction. Tetrahedron Lett., 2009, 50, 2911-2913.
55. Fan, X.S.; Wang, X.; Li, X.Y. An unexpected reaction of cyanothioacetamide: novel preparation of pyrazolo[3,4-b]-pyridine derivatives under MWI. Chin. Chem. Lett., 2008, 19, 643-646.
56. Schenone, S.; Bruno, O.; Fossa, P.; Ranise, A.; Menozzi, G.; Mosti, L.; Bondavalli, F.; Martini, C.; Trincavellib, L. Synthesis and biological Data of 4-Amino-1-(2-chloro-2-phenylethyl)-1H-pyrazolo[3,4-b]pyridine-5- carboxylic acid ethyl esters, a new series of A1-Adenosine Receptor (A1AR) ligands. Bioorg. Med. Chem. Lett., 2001, 11, 2529-2531.
57. Ochiai, H.; Ishida, A.; Ohtani, T.; Kusumi, K.; Kishikawa, K.; Yamamoto, S.; Takeda, H.; Obata, T.; Nakai, H.; Toda, M. Discovery of new orally active Phosphodiesterase (PDE4) inhibitors. Chem. Pharm. Bull., 2004, 52, 1098-1104.
58. Mello, H.; Echevarria, A.; Bernardino, A.M.; Canto-Cavalheiro, M.; Leon, L.L. Antileishmanial pyrazolo-pyridine derivatives: synthesis and structureactivity relationship analysis. J. Med. Chem., 2004, 47, 5427-5432.
59. Mello, H.; Fernandes, E.; Echevarria, A.; Carvalho, M.G.; Bernardino, A.M.R. New derivatives of 1H-pyrazolo[3,4-b]pyridine heterocyclic system: synthesis and hydrogen and carbon assignments by 1D and 2D NMR. Quimica Nova, 1999, 22, 26-30.
60. Quiroga, J.; Insuasty, B.; Cruz, S.; Hernandez, P.; Bolanos, A.; Moreno, R.; Hormaza, A.; De Almeida S.R.H. Reaction of 5-aminopyrazoles with β- dimethylaminopropiophenones. synthesis of new pyrazolo[3,4-b]pyridines. J. Heterocycl. Chem., 1998, 35, 333-338.
61. Quiroga, J.; Insuasty, B.; Abonia, R.; Hernandez, P.; Nogueras, M.; Sanchez, A. Synthesis of pyrazolo[3,4-b]pyridines and pyrido[2,3-d]pyrimidinones by hetero-Diels-Alder reaction of pyrazolyl- and pyrimidinylimines under microwave irradiation in dry media. Heterocycl. Commun., 2000, 6, 345-350.
62. Fadela, S.; Hajbia, Y.; Rakiba, E.M.; Khouilia, M.; Pujolb, M.D.; Guillaumetc, G. Condensation of 2-pyrone with 3-aminopyrazolone. A novel synthesis of pyrazolo[3,4-b]pyridines. Synth. Commun., 2004, 34, 2195-2204.
63. Lacova, M.; Puchala, A.; Solcanyova, E.; Lac, J.; Kois, P.; Chovancova, J.; Rasala, D. 3-Formylchromones IV: the rearrangement of 3-formylchromoneenamines as a simple, facile Route to novel pyrazolo[3,4-b]pyridines and the synthetic utility of the latter. Molecules, 2005, 10, 809-821.
64. Ryabukhin, S.V.; Plaskon, A.S.; Volochnyuk, D.M.; Tolmachev, A.A. Chlorotrimethylsilane-mediated synthesis of functionalized fused pyridines: Reaction of 3-formylchromones with electron-rich aminoheterocycles. Synthesis, 2007, 12, 1861-1871.
65. Stankoviova, H.; Gaplovsky, A.; Lacova, M.; Chovancova, J.; Puchala, A. Transformation of 4-oxo-4H-[1]-benzopyran-3-carboxaldehydes into pyrazolo[ 3,4-b]pyridines. J. Heterocycl. Chem., 2006, 43, 843-848.
66. Lee, S.; Park, S.B. An efficient one-step synthesis of heterobiaryl pyrazolo[ 3,4-b]pyridines via indole ring opening. Org. Lett. 2009, 11, 5214-5217.
67. Abdel-Khalik, M.M.; Agamy, S.M.; Elnagdi, M.H. Chemistry of 2- arylhydrazonopropanals: novel synthesis of 1,6-dihydropyridazines and 5-heteroaryl Substituted pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4- b]pyridines. Synthesis, 2001, 12, 1861-1865.
68. Quiroga, J.; Portilla, J.; Insuasty, B.; Abonia, R.; Nogueras, M.; Sortino, M.; Zacchino, S. Solvent-free microwave synthesis of bis-pyrazolo[3,4-b:4',3'- e]pyridines and study of their antifungal properties. J. Heterocycl. Chem., 2005, 42, 61-66.
69. Lipson, V.V.; Desenko, S.M.; Shirobokava, M.G.; Shishkin, O.V.; Shishkina, S.V. Heterocyclizations of 5-methylpyrazol-3-amine with unsaturated arylaliphatic carboxylic acid derivatives. Russ. J. Org. Chem., 2006, 42,1022-1027.
70. Diaz-Ortiz, A.; Carrillo, J.R.; Cossio, F.P.; Gomez-Escalonilla, M.J.; Hoz, A.; Moreno, A.; Prieto, P. Synthesis of pyrazolo[3,4-b]pyridines by cycloaddition reactions under microwave irradiation. Tetrahedron, 2000, 56, 1569-1577.
71. Dzvinchuk, I.B.; Synthesis of 5-(1H-benzimidazol-2-yl)-1H-pyrazolo-[3,4- b]pyridines by the p-(dimethylamino)benzaldehyde modification of Hantzsch reaction. Chem. Heterocycl. Comp., 2007, 43, 474-479.
72. El-assiery, S.A.; Sayed, G.H.; Fouda, A. Synthesis of some new annulated pyrazolo-pyrido (or pyrano) pyrimidine, pyrazolopyridine and pyranopyrazole derivatives. Acta Pharm., 2004, 54, 143-150.
73. Hamama, W.S. Pyrazolones as versatile precursors for the synthesis of fusedand binary heterocycles. Synth. Commun., 2001, 31, 1335-1345.
74. Mizar, P.; Myrboh, B. Synthetic studies on KF-alumina-catalysed reaction of substituted and unsubstituted aryl-oxoketene dithioacetals and 1H-pyrazone- 5(4H)-one: a convenient synthesis of pyrazolo[3,4-b]pyridine and pyrazolo[ 1,5-a]pyrimidine. Tetrahedron Lett., 2009, 50, 3088-3091.
75. Elgemeie, G.H.; Elghandour, A.H.; Hussein, A.M. Amino acids in heterocyclic synthesis: novel synthesis of pyrano[2,3-c]pyrazoles, pyrazolo[3,4- b]pyridine, and pyrido[1,2-a]benzimidazoles. Synth. Commun., 2004, 34, 3293-3302.
76. Dandia, A.; Arya, K.; Sati, M.; Sharma, R. Facile microwave-assisted onepotsolid phase synthesis of spiro[3H-indole-3,4'-pyrazolo[3,4-b]pyridines]. Heterocycl. Commun., 2003, 9, 415-420.
77. P. Friedlander, Ber., 1882, 15, 2572.
78. Jones, G. The Chemistry of Heterocyclic Compounds, Quinoline, Part 1; G. Jones, Ed.; John Wiley & Sons: New York, 1977; Vol. 32, pp. 181-189.
79. Aly, E.A.; Abdo, M.A.; El-Gharably, A.A. Heteroannelations with o-amino aldehyde and o-amino cyano of some pyrazole derivatives. Afinidad, 2004, 61, 510-515.
80. Jachak, M.N.; Avhale, A.B.; Tantak, C.D., Toche, R.B; Reidlinger, C.; Stadlbauer, W. Friedländer condensation of 5-aminopyrazole-4- carbaldehydes with reactive α-methylene ketones: Synthesis of pyrazolo[3,4- b]pyridines. J. Heterocycl. Chem., 2005, 42, 1311-1319.
81. Sabitha, G.; Srividya, R.; Archana, B.; Yadav, J.S. A facile route to pyrazolo[ 3,4-b]pyridines and benzopyrano[4,3,e]pyrazolo[3,4-b]Pyridines. Synth. Commun., 1999, 29, 655-665.
82. Hussein, A.M.; El-Emary, T. I. Polycyclic pyrazoles: routes to new pyrazoloazines. J. Chem. Res. (S), 1998, 1, 20-21.
83. Ahluwalia, V. K.; Goyal, B. A facile synthesis of pyrazolo[3,4-b]pyridines. Synth. Commun., 1996, 26, 1341-1343.
84. Abd-El-Latif, F.M.; Barsy, M.A.; Elrady, E.A.; Hassan, M. New routes for novel pyrazolo[3,4-b][1,6]-naphthyridine, pyrazolo[3,4-b]pyridine and pyrazolo[3,4:2,3]pyrido[6,1-a]benzimidazole derivatives. J. Chem. Res. (S), 1999, 12, 696-697.
85. Ahluwalia, V. K.; Dahiya, A.; Garg, V. K. Reaction of 5-amino-4-formyl-3- methyl (or phenyl)-1-phenyl-1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings. Indian J. Chem. Sect. B, 1997, 36, 88-90.
86. Zheng, A.; Zhang, W.; Pan, J. One-Pot and convenient conversion of 5- azidopyrazole-4-carboxaldehyde to pyrazolo[3,4-b]pyridines. Synth. Commun., 2006, 36, 1549-1556.
87. Zhao, W.G.; Li, Z.M.; Yuan, D.K. A novel and facile synthesis of pyrazolo[ 3,4-b]pyridines. J. Chem. Res. (S), 2002, 9, 454-455.
88. Salaheldin, A.M.; Oliveira-Campos, A.M.F.; Rodrigues, L.M. Heterocyclic Synthesis with nitriles: synthesis of pyrazolopyrimidine and pyrazolopyridine Derivatives. Synth. Commun., 2009, 39, 1186-1195.
89. El-Sayed Ali, T. Synthesis of some novel pyrazolo[3,4-b]pyridine and pyrazolo[ 3,4-d]pyrimidine derivatives bearing 5,6-diphenyl-1,2,4-triazine moiety as potential antimicrobial agents. Eur. J. Med. Chem., 2009, 44, 4385-4392.
90. Beutner, G.L.; Kuethe, J.T.; Kim, M.M.; Yasuda, N. Expedient synthesis of 3-alkoxymethyl and 3-aminomethyl pyrazolo[3,4-b]pyridines. J. Org. Chem., 2009, 74, 789-794.
91. Lavecchia, G.; Berteina-Raboin, S.; Guillaumet, G. Synthesis of 3,5- difunctionalized-1-methyl-1H-pyrazolo[3,4-b]pyridines involving palladiummediated coupling reactions. Tetrahedron Lett., 2004, 45, 6633-6636.
92. Dai, Y.; Hartandi, K.; Soni, N.B.; Pease, L.J.; Reuter, D.R.; Olson, A.M.; Osterling, D.J.; Doktor, S.Z.; Albert, D.H.; Bouska, J.J.; Glaser, K.B.; Marcotte, P.A.; Stewart, K.D.; Davidsen, S.K.; Michaelides, M.R. Identification of aminopyrazolopyridine ureas as potent VEGFR/PDGFR multitargeted kinase inhibitors. Bioorg. Med. Chem. Lett., 2008, 18, 386-390.
93. Swelam, S.A. Facile and simple syntheses of heterocyclic compounds based on pyridine and pyrazolopyridine derivatives. Oriental J. Chem., 2008, 24, 105-114.
94. Yassin, F. A. Synthesis, reactions and biological activity of 2-substituted 3- cyano-4,6-dimethylpyridine derivatives. Chem. Heterocycl. Comp., 2009, 45, 35-41.
95. Chioua, M.; Samadi, A.; Soriano, E.; Lozach, O.; Meijer, L.; Marco Contelles, J. Synthesis and biological evaluation of 3,6-diamino-1Hpyrazolo[ 3,4-b]pyridine derivatives as protein kinase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19, 4566-4569.
96. Hamdy, N.A.; Gamal-Eldeen, A.M. New pyridone, thioxopyridine, pyrazolopyridine and pyridine derivatives that modulate inflammatory mediators in stimulated RAW 2647 murine macrophage. Eur. J. Med. Chem., 2009, 44, 4547-4556.
97. El-neairy, M.A.A. Utility of cyanothioacetamide and its derivatives in heterocyclic synthesis: syntheis and characterization of several new pyridine, pyrazolo-[3,4-b]pyridine, thieno[2,3-b]pyridine and pyrido[5,4-b] thieno[3',2'-d'] pyrimidine derivatives. Phosphorus, Sulfur, and Silicon, 1999, 148, 189-200.
98. Gad-Elkareem, M.A.M.; Abdel-Fattah, A.M.; Elneairy, M.A.A. Pyridine- 2(1H)-thione in heterocyclic synthesis: synthesis of some new nicotinic acid ester, thieno[2,3-b]pyridine, pyrido[3',2':4,5]thieno[3,2-d]pyrimidine and thiazolylpyrazolo-[3,4-b]pyridine derivatives. Phosphorus, Sulfur, and Silicon, 2006, 181, 891-911.
99. Attaby, F.A.; Ali, M.A.; Ibrahem, Y.M.; Elghandour, A.H.H. Synthesis, reactions, and antiviral activity of 1-(1H-Pyrazolo[3,4-b]pyridin-5-yl)ethanone and pyrido[2',3':3,4]pyrazolo[5,1-c][1,2,4]triazine derivatives. Phosphorus, Sulfur, and Silicon, 2006, 181, 1087-1102.
100. Kheder, N.A.; Mabkhot, Y.N.; Farag, A.M. Facile and convenient synthesis of pyrazole, pyridine, pyridazine, pyrazolo[3,4-b]pyridine, and pyrazolo[5,1- c][1,2,4]triazine Derivatives. Synth. Commun., 2008, 38, 3170-3182.
101. Attaby, F.A.; El-neairy, M.A.A.; Elsayed, M.S. Synthesis and antimicrobial evaluation of several new pyridine, thienopyridine and pyridothienopyrazole derivatives. Phosphorus, Sulfur, and Silicon, 1999, 149, 49-64.
102. Abdel-Fattah, A.M.; Elneairy, M.A.A.; Gad-Elkareem, M.A.M. A novel synthesis of pyridine-2(1H)-thione, pyrazolo[3,4-b]pyridine, pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine, thieno[2,3-b]pyridine, and pyrido[3',2':4,5]thieno[3,2-d]pyrimidine derivatives containing a naphthyl moiety. Phosphorus, Sulfur, and Silicon, 2007, 182, 1351-1364.
103. Goda, F.E.; Abdel-Azizb, A.A.-M.; Attef, O.A. Synthesis, antimicrobial activity and conformational analysis of novel substituted pyridines: BF3- promoted reaction of hydrazine with 2-alkoxy pyridines. Bioorg. Med.Chem., 2004, 12, 1845-1852.
104. Cappelli, A.; Nannicini, C.; Gallelli, A.; Giuliani, G.; Valenti, S.; Mohr, G.P.; Anzini, M.; Mennuni, L.; Ferrari, F.; Caselli, G.; Giordani, A.; Peris, W.; Makovec, F.; Giorgi, G.; Vomero, S. Design, synthesis, and biological evaluation of AT1 Angiotensin-II receptor antagonists based on the pyrazolo[ 3,4-b]pyridine and related heteroaromatic bicyclic systems. J. Med. Chem., 2008, 51, 2137-2146.
105. Zhong, Y.-L.; Lindale, M.G.; Yasuda, N. An efficient access to 3,6- disubstituted 1H-pyrazolo[3,4-b]pyridines via a one-pot double SNAr reactionand pyrazole formation. Tetrahedron Lett., 2009, 50, 2293-2297.
106. Henke, B.R.; Aquino, C.J.; Birkemo, L.S.; Croom, D.K.; Dougherty, R.W.; Ervin, G.N.; Grizzle, M.K; Hirst, G.C.; James, M.K.; Johnson, M.F.; Queen, K.L.; Sherrill, R.G.; Sugg, E.; Suh, E.M.; Szewczyk, J.W.; Unwalla, R.J.; Yingling, J.; Willson, T.M. Optimization of 3-(1H-Indazol-3-ylmethyl)-1,5- benzodiazepines as potent, orally Active CCK-A Agonists. J. Med. Chem., 1997, 40, 2706-2725.
107. Sweeney, Z.K.; Harris, S.F.; Arora, N.; Javanbakht, H.; Li, Y.; Fretland, J.; Davidson, J.P.; Billedeau, J.R.; Gleason, S.K.; Hirschfeld, D.; Kennedy-Smith, J.J.; Mirzadegan, T.; Roetz, R.; Smith, M.; Sperry, S.; Suh, J.M.; Wu, J.; Tsing, S.; Villase, A.G.; Paul, A.; Su, G.; Heilek, G.; Hang, J.Q.; Zhou, A.S.; Jernelius, J.A.; Zhang, F.-J.; Klumpp, K. Design of annulated pyrazoles as inhibitors of HIV-1 reverse transcriptase. J. Med. Chem., 2008, 51, 7449-7458.
108. Revesz, L.; Blum, E.; Di Padova, F.E.; Buhl, T.; Feifel, R.; Gram, H.; Hiestand, P.; Manning, U.; Neumann, U.; Rucklin, G. Pyrazoloheteroaryls:novel p38α MAP kinase inhibiting scaffolds with oral activity. Bioorg. Med. Chem. Lett., 2006, 16, 262-266.
109. Sagitullina, G.P.; Lisitskaya, L.A.; Vorontsova, M.A.; Sagitullin, R.S. Facile synthesis of substituted 1H-pyrazolo[3,4-b]pyridines. Mendeleev Commun., 2007, 17, 192-193.
110. Kidwai, M.; Thakur, R.; Saxena, S. A facile synthesis of substituted pyridines and pyrazolo[3,4-b]pyridines. J. Heterocycl. Chem., 2005, 42, 1311-1319.
111. Kolosov, M. A.; Orlov, V. D.; Kolos, N. N.; Shishkin, O. V.; Zubatyukb, R. I. Reactions of α-cyanochalcones with phenylhydrazine. Arkivoc 2007, (14), 187-194.
112. Wardakhan, W.W.; Agami, S.M. Reaction of benzoyl acetonitrile with acetoacetanilides: synthesis of some pyrazole, pyrimidine, pyrazolo[3,4-b]pyridine and pyrido[2,3-d]pyrimidine derivatives. Egypt. J. Chem., 2001, 44, 315-333.