Simple and Efficient Method for Synthesis of 3-Cyano-6,7-diarylpyrazolo[1,5-a]pyrimidine from Isoflavones

REFERENCES

• Moritani , Y. ; Shirai , K. ; Oi , M. Pyrazolo[1,5-a]pyrimidine compounds as cannabinoid receptor antagonists . PCT Int. Appl. WO patent 2007046548.
   Google Scholar
• Mukaiyama , H. ; Nishimura , T. ; Kobayashi , S. ; Komatsu , Y. Pyrazolo[1,5-a]pyrimidines as c-Src kinase inhibitors that reduce IKr channel blockade . Bioorg. Med. Chem. 2008 , 16 , 909 – 921 .
   PubMed Web of Science ®Google Scholar
• Huang , S. ; Lin , R. ; Yu , Y. ; Lu , Y. ; Connolly , P. ; Chiu , G. ; Li , S. ; Emanuel , S. ; Middleton , S. Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor . Bioorg. Med. Chem. Lett. 2007 , 17 , 1243 – 1245 .
   PubMed Web of Science ®Google Scholar
• Saggar , S. ; Sisko , J. ; Tucker , T. ; Tynebor , R. ; Su , D. ; Anthony , N. Acoustic alert communication system with enhanced signal to noise . U.S. Patent Appl. 2007021442.
   Google Scholar
• Zhang , P. ; Pennell , M. ; Wright , J. ; Chen , W. ; Leleti , M. ; Li , Y. ; Li , L. ; Xu , Y. Azaindazole compounds and methods of use . PCT Int. Appl. WO patent 2007002293.
   Google Scholar
• (a) Chiu , G. ; Li , S. ; Connolly , P. ; Middleton , S. ; Emanuel , S. ; Huang , S. ; Lin , R. ; Lu , Y. 3-benzoimidazolyl-pyrazolopyrimidines useful in treatings kinase disorders disubstituted derivatives . PCT Int. Appl. WO patent 2006130673 ; (b) Dwyer , M. ; Paruch , K. ; Alvarez , C. ; Doll , R. ; Keertikar , K. ; Duca , J. ; Fischmann , T. ; Hruza , A. ; Madison , V. ; Lees , E. ; Parry , D. ; Seghezzi , W. ; Sgambellone , N. ; Shanahan , F. ; Wiswellb , D. ; Guzia , T. Versatile templates for the development of novel kinase inhibitors: Discovery of novel CDK inhibitors . Bioorg. Med. Chem. Lett. 2007 , 17 , 6216 – 6219 .
   PubMed Web of Science ®Google Scholar
• Feurer , A. ; Luithle , J. ; Wirtz , S. ; Koenig , G. ; Stasch , J. ; Stahl , E. ; Schreiber , R. ; Wunder , F. ; Lang , D. Novel 2,5-disubstituted pyrimidine derivatives . PCT Int. Appl. WO patent 2004009589 .
   Google Scholar
• (a) Demircali , A. ; Karci , F. Synthesis and solvatochromic properties of some disazo dyes derived from pyrazolo[1,5-a]pyrimidine derivatives . Dyes Pigments 2005 , 64 , 259 – 264 ; (b) Tsai , P. C. ; Wang , I. J. Crystal violet;dDecoloration; photolytic oxidation; UV/H2O2; Fenton's reagent . Dyes Pigments 2007 , 74 , 288 – 297 ; (c) Tsai , P. C. ; Wang , I. Synthesis and solvatochromic properties of 3,6-bishetarylazo dyes derived from pyrazolo[1,5-a]pyrimidine . Dyes Pigments 2008 , 76 , 575 – 581 .
   Web of Science ®Google Scholar
• (a) Elnagdi , M. H. ; Elmoghayar , M. R. H. ; Elgemeie , G. H. Chemistry of pyrazolo- pyrimidines . Adv. Heterocycl. Chem. 1987 , 41 , 319 – 376 ; (b) Quiroga , J. ; Hormaza , A. ; Insuasty , B. ; Saitz , C. ; Jullian , C. ; Canete , A. Synthesis of pyrazolo[1,5-a]pyrimidines in the reaction of 5-amino-3-arylpyrazoles with methoxymethylene Meldrum's acid derivatives and thermolysis of their pyrazolylaminomethylene derivatives . J. Heterocycl. Chem. 1998 , 35 , 61 – 64 ; (c) El-Taweel , F. ; Abu Elmaati , T. Cyclization reactions of 5-aminopyrazoles with β-ketoesters, enamines, and β-keto anilides: New synthetic routes to pyrazolo[1,5-a] pyrimidine derivatives . J. Chin. Chem. Soc. 2002 , 49 , 1051 – 1055 ; (d) Daniels , R. ; Kim , K. ; Lebois , E. ; Muchalski , H. ; Hughes , M. ; Lindsley , C. Microwave-assisted protocols for the expedited synthesis of pyrazolo[l,5-a]pyrimidine and [3,4-d]pyrimidines . Tetrahedron Lett. 2008 , 49 , 305 – 310 .
   Web of Science ®Google Scholar
• (a) Simon , C. ; Constantieux , T. ; Rodriguez , J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions. Eur. J. Org. Chem. 2004, 24, 4957–4980; (b) Quiroga , J. ; Portilla , J. ; Abonía , R. ; Insuasty , B. ; Nogueras , M. ; Cobo , J. Regioselective synthesis of novel polyfunctionally substituted pyrazolo[l,5-a]pyrimidines under solvent-free conditions. Tetrahedron Lett. 2007, 48, 6352–6355; (c) Quiroga , J. ; Mejía , D. ; Insuasty , B. ; Abonía , R. ; Nogueras , M. ; Sanchez , A. ; Cobo , J. Synthesis of 6-(2-hydroxybenzoyl)pyrazolo[1,5-a] pyrimidines by reaction of 5-amino-1H-pyrazoles and 3-formylchromone. J. Heterocycl. Chem. 2002, 39, 51–54.
   Web of Science ®Google Scholar
• (a) Shipps , Jr. , G. W. ; Rosner , K. E. ; Popovici-Muller , J. ; Deng , Y.-Q. ; Wang , T. ; Curran , P. J. Preparation of pyrazolo[1,5-a]pyrimidine compounds as antiviral agents against hepatitis C virus (HCV) infection . PCT Int. Appl. WO patent 2003101993 ; (b) Paruch , K. ; Guzi , T. J. ; Dwyer , M. P. ; Shipps , G. W. Preparation of a novel class of pyrazolopyrimidines as inhibitors of protein and checkpoint kinases useful in treatment and prophylaxis of HCV infection and other diseases such as cancer . U.S. Patent Appl. Publ. 2006094706 A1 .
   Google Scholar
• Zhang , Z.-T. ; Tan , D.-J. ; Xue , D. A concise one-pot synthesis of 3,4-diaryl-1H-pyrazoles from natural isoflavones and hydrazine hydrate . Helv. Chim. Acta 2007 , 90 , 2096 – 2108 .
   Web of Science ®Google Scholar
• Zhang , Z.-T. ; Xu , F.-F. ; Gao , M.-X. ; Qiu , L. One-pot synthesis of 4,5-biphenyl-2-pyrimidinylguanidine derivatives . J. Comb. Chem. 2009 , 11 , 880 – 885 .
   PubMed Web of Science ®Google Scholar
• Zhang , Z.-T. ; Qiu , L. ; Xue , D. ; Wu , J. ; Xu , F.-F. Concise synthesis of 2, 3-diarylpyrimido [1,2-a]benzimidazole based on isoflavones . J. Comb. Chem. 2010 , 12 , 225 – 230 .
   PubMed Web of Science ®Google Scholar