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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 6
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Original Articles

Synthesis of New Pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines and Their Use in the Preparation of Tetraheterocyclic Systems

Pages 877-887 | Received 19 Apr 2009, Published online: 22 Feb 2010

REFERENCES

  • Menezes , C. M. S. ; Santá Anna , C. M. R. ; Rodrigues , C. R. ; Barreiro , E. J. J. Molecular modeling of novel 1H-pyrazolo[3,4-b]pyridine derivatives designed as isosters of the antimalarial mefloquine . Theochem. 2002 , 579 , 31 – 39 .
  • Poreba , K. ; Oplski , A. ; Wietrezyk , J. Synthesis and antiproliferative activity in vitro of new 3-substituted aminopyrazolo[3,4-b]pyridines . Acta. Pol. Pharm. 2002 , 59 , 215 .
  • Goda , F. E. ; Abedl-Aziz , A. A. M. ; Attef , O. A. Synthesis and antiproliferative activity in vitro of new 3-substituted aminopyrazolo[3,4-b]pyridines . Bioorg. Med. Chem. 2004 , 12 , 1845 – 1852 .
  • Attaby , F. A. ; Abdel-Fattah , A. M. A novel synthesis of thienopyridine, pyrroloquinolinothiophene, pyrazolopyridine-3-yl-phenylthiourea, and thiazolylpyrazolopyridine derivatives . Phosphorus, Sulfur Silicon Relat. Elem. 1999 , 155 , 253 – 270 .
  • Eleairy , M. A. A. ; Attaby , F. A. ; Elsayed , M. S. Synthesis of thiazole, triazole, pyrazolo[3,4-b]-pyridinyl-3-phenylthiourea, aminopyrazolo[3,4-b]pyridine derivatives and their biological evaluation . Phosphorus, Sulfur Silicon Relat. Elem. 2000 , 167 , 161 – 179 .
  • Stasch , J. P. ; Dembowsky , K. ; Perzborn , E. ; Stahl , E. ; Br Schramm , M. Cardiovascular actions of a novel NO-independent guanylyl cyclase stimulator, BAY 41-8543: In vivo studies . Br. J. Pharmacol. 2002 , 135 , 344 – 355 .
  • Boerrigter , G. ; Costello-Boerrigter , L. C. ; Cataliotti , A. ; Tsuruda , T. ; Harty , G. J. ; Lapp , H. ; Stasch , J. P. ; Burnett , J. C. Cardiorenal and humoral properties of a novel direct soluble guanylate cyclase stimulator BAY 41-2272 in experimental congestive heart failure . Circulation 2003 , 107 , 686 – 689 .
  • Bawankule , D. U. ; Stathishkumar , K. ; Sardar , K. K. ; Chanda , D. ; Krishna , A. V. ; Prakash , V. R. ; Mishra , S. K. [5-Cyclopropyl-2-[1-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine]-induced dilation in ovine pulmonary artery: Role of sodium pump . J. Pharmacol. Exp. Ther. 2005 , 314 , 207 – 213 .
  • Attaby , F. A. ; Elghandour , A. H. H. ; Ali , M. A. ; Ibrahim , Y. M. 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 Silicon Relat. Elem. 2006 , 181 , 1087 – 1102 .
  • Attaby , F. A. ; Elghandour , A. H. H. ; Ali , M. A. ; Ibrahim , Y. M. Synthesis, characterization, and antiviral activities of pyridopyrazolotriazines . Phosphorus, Sulfur Silicon Relat. Elem. 2007 , 182 , 133 – 149 .
  • Azevedo , A. R. ; Ferreira , V. F. ; de Mello , H. ; Leao-Ferreira , L. R. ; Jabor , A. V. ; Frugulhetti , I. C. P. P. ; Pereira , H. S. ; Moussatche , N. ; Bernardino , A. M. R. Synthesis and biological evaluation of 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acids against Vaccinia virus . Heterocycl. Commun. 2002 , 8 , 427 – 432 .
  • De Mello , H. ; Echevarria , A. ; Bernardino , A. M. ; Canto-Cavalheiro , M. ; Leon , L. L. Antileishmanial pyrazolopyridine derivatives: Synthesis and structure−activity relationship analysis . J. Med. Chem. 2004 , 47 , 5427 – 5432 .
  • Misra , R. N. ; Xiao , H. Y. ; Rawlins , D. B. ; Shan , W. ; Kellar , K. A. ; Mulheron , J. G. ; Sack , J. S. ; Tokarski , J. S. ; Kimball , S. D. ; Webster , K. R. 1H-Pyrazolo[3,4-b]pyridine inhibitors of cyclin-dependent kinases: Highly potent 2,6-difluorophenacyl analogues . Biorg. Med. Chem. Lett. 2003 , 13 , 2405 .
  • Poeba , K. ; Opolski , A. ; Wietrzyk , J. ; Kowalska , M. Synthesis and antiproliferative activity in vitro of new derivatives of 3-aminopyrazolo[3,4-b]pyridine, part 1: Reaction of 3-aminopyrazolo[3,4-b]pyridine with 1,3-, 1,4-diketones and α,β-unsaturated ketones . Arch. Pharm. 2001 , 334 , 219 – 223 .
  • Alberti , M. J. ; Auten , E. P. ; Lackey , K. E. ; McDonald , O. B. ; Wood , E. R. ; Preugschat , F. ; Cutler , G. J. ; Kane-Carson , L. ; Liu , W. ; Jung , D. K. Discovery and in vitro evaluation of potent kinase inhibitors: Pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidines. Bioorg. Med. Chem. Lett. 2005, 15, 3778–3781.
  • Sekikawa , I. ; Nishie , J. ; Tono-Oka , S. ; Tanaka , Y. ; Kakimoto , S. Antituberculous compounds, XXVIII: Synthesis of pyrazolopyridines . J. Heterocycl. Chem. 1973 , 10 , 931 – 932 .
  • Kukzynski , L. ; Mrizikiewiez , A. ; Banaszkiewicz , W. ; Poreba , K. Synthesis and biological activity of pyrazo-[3,4-b]-pyridine derivatives, part I . Pol. J. Pharmacol. Pharm. 1979 , 31 , 217 .
  • Kamal , A. M. ; Atalla , A. A. ; Mohamed , T. A. ; Gies , A. A. Synthesis of some pyrazolopyridine sulphonamide derivatives . Z. Naturforsch. B: Chem. Sci. 1991 , 46 , 541 – 546 .
  • Novinson , T. ; Hanson , R. ; Dimmitt , M. K. ; Simon , L. N. ; Robins , R. K. ; Obrien , D. E. 3-Substituted 5,7-dimethylpyrazolo[1,5-a]pyrimidines, 3′,5′-cyclic AMP phosphodiesterase inhibitors . J. Med. Chem. 1974 , 17 , 645 – 648 .
  • Novinson , T. ; Miller , J. P. ; Scholten , M. ; Robins , R. K. ; Simon , L. N. ; Obrien , D. E. ; Meyer , R. B. Adenosine cyclic 3′,5′-monophosphate phosphodiesterase inhibitors, 2. 3-Substituted 5,7-dialkylpyrazolo[1,5-a]pyrimidines . J. Med. Chem. 1975 , 18 , 460 – 464 .
  • Kirkpatrich , W. E. ; Okabe , T. ; Hillyard , I. W. ; Robins , R. K. ; Dren , A. T. ; Novinson , T. 3-Halo-5,7-dimethylpyrazolo[1,5-A]pyrimidines, a nonbenzodiazepinoid class of antianxiety agents devoid of potentiation of central nervous system depressant effects of ethanol or barbiturates . J. Med. Chem. 1977 , 20 , 386 – 393 .
  • Chandra , A. S. R. ; Narsaiah , B. ; Venkataratnam , R. V. A new synthetic route to fluorinated pyrazolo[3,4-b]pyridines and their use in the preparation of novel pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines . J. Flourine Chem. 1997 , 86 , 127 – 130 .
  • Krishanaiah , A. ; Narsaiah , B. A facile method for synthesis of novel fluorinated pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines . J. Flourine Chem. 2001 , 109 , 183 – 187 .
  • Kanth , R. S. ; Reddy , G. V. ; Maitraie , D. ; Narsaiah , B. ; Shanthan , R. P. ; Kumar , K. R. ; Sridhar , B. Iron(III) chloride catalysed three-component Grieco condensation: Synthesis of tetrahydropyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines/quinazolines . J. Flourine Chem. 2006 , 127 , 1211 – 1221 .
  • Mohamed , A. M. G. ; Azza , M. ; Mohamed , A. A. E. Pyrazlo[3,4-b]pyridine in heterocyclic synthesis: Synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1′,2′:1,5]pyrazolo[3,4-b]pyridines, and pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines . Can. J. Chem. 2007 , 85 , 592 – 599 .
  • Hojo , M. ; Masuda , R. ; Kokuryo , Y. ; Shioda , H. ; Matsuo , S. Electrophilic substitutions of olefinic hydrogenes II: Acylation of vinyl ethers and N-vinyl amides . Chem. Lett. 1976 , 499 – 502 .
  • Hojo , M. ; Masuda , R. ; Okada , E. A convenient synthetic route to functionalized 5-trifluoroacetyl-6-trifluoromethyl-3,4-dihydro-2H-pyrans: Hetero-Diels–Alder reaction of β,β-bis(trifluoroacetyl)vinyl ethers with electron-rich alkenes . Synthesis 1990 , 347 – 350 .

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