Simultaneous Synthesis of Pyrazolopyridines and Pyrazolopyrimidinones Under Microwave Irradiation

REFERENCES

• Katritzky , A. R. ; Rees , C. W. ; Scriven , E. F. V. Comprehensive Heterocyclic Chemistry II ; Pergamon : New York , 1996 .
   Google Scholar
• Dunn , P. J. Synthesis of commercial phosphodiesterase(V) inhibitors . Org. Process Res. Dev. 2005 , 9 , 88 – 97 .
   Google Scholar
• Allerton , C. M. N. ; Barber , C. G. ; Beaumont , K. C. ; Brown , D. G. ; Cole , S. M. ; Ellis , D. ; Lane , C. A. L. ; Maw , G. N. ; Mount , N. M. ; Rawson , D. J. ; Robinson , C. M. ; Street , S. D. A. ; Summerhill , N. W. A novel series of potent and selective PDE5 inhibitors with potential for high and dose-independent oral bioavailability . J. Med. Chem. 2006 , 49 , 3581 – 3594 .
   PubMedGoogle Scholar
• Markwalder , J. A. ; Arnone , M. R. ; Benfield , P. A. ; Boisclair , M. ; Burton , C. R. ; Chang , C. H. ; Cox , S. S. ; Czerniak , P. M. ; Dean , C. L. ; Doleniak , D. ; Grafstrom , R. ; Harrison , B. A. ; Kaltenbach , R. F. III ; Nugiel , D. A. ; Rossi , K. A. ; Sherk , S. R. ; Sisk , L. M. ; Stouten , P. ; Trainor , G. L. ; Worland , P. ; Seitz , S. P. Synthesis and biological evaluation of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one inhibitors of cyclin-dependent kinases . J. Med. Chem. 2004 , 47 , 5894 – 5911 .
   PubMed Web of Science ®Google Scholar
• Bontems , R. J. ; Anderson , J. D. ; Smee , D. F. ; Jin , A. ; Alaghamandan , H. A. ; Sharma , B. S. ; Jolley , W. B. ; Robins , R. K. ; Cottam , H. B. Guanosine analogs: Synthesis of nucleosides of certain 3-substituted 6-aminopyrazolo[3,4-d]pyrimidin-4(5 H)-ones as potential immunotherapeutic agents . J. Med. Chem. 1990 , 33 , 2174 – 2178 .
   PubMed Web of Science ®Google Scholar
• Xia , Y. ; Chackalamannil , S. ; Czarniecki , M. ; Tsai , H. ; Vaccaro , H. ; Cleven , R. ; Cook , J. ; Fawzi , A. ; Watkins , R. ; Zhang , H. Synthesis and evaluation of polycyclic pyrazolo[3,4-d]pyrimidines as PDE1 and PDE5 cGMP phosphodiesterase inhibitors. J. Med. Chem. 1997, 40, 4372–4377.
   PubMed Web of Science ®Google Scholar
• Yu , G. ; Mason , H. J. ; Wu , X. ; Wang , J. ; Chong , S. ; Dorough , G. ; Henwood , A. ; Pongrac , R. ; Seliger , L. ; He , B. ; Normandin , D. ; Adam , L. ; Krupinski , J. ; Macor , J. E. Substituted pyrazolopyridines as potent and selective PDE5 inhibitors: Potential agents for treatment of erectile dysfunction . J. Med. Chem. 2001 , 44 , 1025 – 1027 .
   PubMed Web of Science ®Google Scholar
• Dornow , A. ; Siebrecht , M. Synthesen stickstoffhaltiger Heterocyclen, XXII: Über die Synthese einiger Pyrazolo[3.4-b]pyridine . Chem. Ber. 2006 , 93 , 1106 – 1110 .
   Google Scholar
• Rawlings , D. A. Pyrazolo[3,4-c]pyridines as GSK-3 inhibitors. US patent 7105532 , 2006 .
   Google Scholar
• Schenone , S. ; Bruno , O. ; Fossa , P. ; Ranise , A. ; Menozzi , G. ; Mosti , L. ; Bondavalli , F. ; Martini , C. ; Trincavelli , 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 .
   PubMed Web of Science ®Google Scholar
• Tominaga , Y. ; Honkawa , Y. ; Hara , M. ; Hosomi , A. Heteroaromatization with ketene dithioacetals, part I: Synthesis of some novel 5-amino-1-(1,3,4-thiadiazol-2-yl) and 1-(1,3,4-thiadiazin-2-yl)pyrazole-4-carbonitriles . J. Heterocycl. Chem. 1990 , 27 , 775 – 783 .
   Web of Science ®Google Scholar
• Adams , N. D. ; Schmidt , S. J. ; Knight , S. D. ; Dhanak , D. A novel synthesis of substituted 4H-pyrazolo[3,4-d]pyrimidin-4-ones . Tetrahedron Lett. 2007 , 48 , 3983 – 3986 .
   Google Scholar
• Cheng , C. C. ; Robins , R. K. Potential purine antagonists, VI: Synthesis of 1-alkyl- and 1-aryl-4-substituted pyrazolo[3,4-d]pyrimidines . J. Org. Chem. 1956 , 21 , 1240 – 1256 .
   Web of Science ®Google Scholar
• Marttnez-Grau , A. ; Marco , J. L. Friedlander reaction on 2-amino-3-cyano-4 h-pyrans: Synthesis of derivatives of 4 H-pyran [2,3-b] quinoline, new tacrine analogues . Bioorg. Med. Chem. Lett. 1997 , 7 , 3165 – 3170 .
   Google Scholar
• Pinner , A. ; Klein , F. Umwandlung der Nitrile in Irnide . Ber. Dtsch. Chem. Ges. 1877 , 10 , 1899 .
   Google Scholar
• Rozhkov , V. Y. ; Batog , L. V. ; Shevtsova , E. K. ; Struchkova , M. I. Synthesis and dimroth rearrangement of 3-amino-4-(5-amino-1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles . Mendeleev Commun. 2004 , 14 , 76 – 77 .
   Web of Science ®Google Scholar