Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 9
422
Views
38
CrossRef citations to date
0
Altmetric
Original Articles

Phosphomolybdic Acid: An Efficient and Recyclable Solid Acid Catalyst for the Synthesis of 4,4′-(Arylmethylene)bis(1H-pyrazol-5-ols)

, , , , &
Pages 1349-1358 | Received 16 Aug 2010, Published online: 11 Jan 2012

REFERENCES

  • Awadallah , F. M. ; Muller , F. ; Lehmann , A. H. ; Abadi , A. H. Synthesis of novel lactam derivatives and their evaluation as ligands for the dopamine receptors, leading to D4-selective ligand . Bioorg. Med. Chem. 2007 , 15 , 5811 – 5818 .
  • Bagley , M. C. ; Davis , T. ; Dix , M. C. ; Rokicki , M. J. ; Kipling , D. Rapid synthesis of VX-745: p38 MAP kinase inhibition in Werner syndrome calls . Bioorg. Med Chem. Lett. 2007 , 17 , 5107 – 5110 .
  • McDonald , E. ; Jones , K. ; Brough , P. A. ; Drysdale , M. J. ; Workman , P. Discovery and development of pyrazole scaffold Hsp90 inhibitors . Curr. Top. Med. Chem. 2006 , 6 , 1193 – 1203 .
  • Nakagawa , H. ; Ohyama , R. ; Kimata , A. ; Suzuki , T. ; Miyata , N. Hydroxyl radical scavenging by edaravone derivatives: Efficient scavenging by 3-methyl-1-(pyridin-2-yl)-5-pyrazolone with an intramolecular base . Bioorg. Med Chem. Lett. 2006 , 16 , 5939 – 5942 .
  • Bailey , D. M. ; Hansen , P. E. ; Hlavac , A. G. ; Baizman , E. R. ; Pearl , J. ; Defelice , A. F. ; Feigenson , M. E. 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. J. Med. Chem. 1985, 28, 256–260.
  • Mahajan , R. N. ; Havaldar , F. H. ; Fernandes , P. S. Synthesis and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate . J. Indian Chem. Soc. 1991 , 68 , 245 – 246 .
  • Sugiura , S. ; Ohno , S. ; Ohtani , O. , Izumi , K. , Kitamikado , T. , Asai , H. , Kato , K. Syntheses and anti-inflammatory and hypnotic activity of 5-alkoxy-3-(N-substituted carbamoyl)-1-phenylpyrazoles, 4 . J. Med. Chem. 1977 , 20 , 80 – 85 .
  • Behr , L. C. ; Fusco , R. ; Jarboe , C. H. In The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles, and Condensed Rings ; A. Weissberger (Ed.); Interscience : New York , 1967 ; p. 22 .
  • Genin , M. J. ; Biles , C. ; Keiser , B. J. ; Poppe , S. M. ; Swaney , S. M. ; Tarpley , W. G. ; Romero , D. L. Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives . J. Med. Chem. 2000 , 43 , 1034 – 1040 .
  • Yang , J. ; Gharagozloo , P. ; Yao , J. ; Ilyin , V.I. ; Carter , R. B. ; Nguyen , P. ; Robledo , S. ; Woodward , R. M. ; Hogenkamp , D. J. 3-(4-Phenoxyphenyl)pyrazoles: A novel class of sodium channel blockers . J. Med. Chem. 2004 , 47 , 1547 – 1552 .
  • Uzoukwu , A. B. ; Al-Juaid , S. S. ; Hitchcock , P. B. ; Smith , J. D. The synthesis and crystal structures of 1-phenyl-3-methyl-4-butanolpyrazole-5-one and of two pyrazolonato complex of iron . Polyhedron 1993 , 12 , 2719 – 2724 .
  • Maurya , R. C. ; Verma , R. Synthesis and characterizaton of some novel mixed-ligand cyanonitrosyl {MnNO}6 complexes of manganese (I) with biologically active oxygen donor 2- or 3-pyrazoline-5-one derivatives . Indian J. Chem. Sect. A. 1997 , 36A , 596 – 598 .
  • (a) Garnovskii , A. D. ; Uraev , A. I. ; Minkin , V. I. Metal complexes from aryl and hetarylazocompounds . Arkivoc 2004 , 3 , 29 – 41 ; (b) Pettinari , C. ; Marchetti , F. ; Pettinari , R. ; Drozdov , A. ; Troyanov , S. ; Voloshin , A. I. ; Shavaleen , N. M. Synthesis, structure, and luminescence properties of new rare earth metal complexes with 1-phenyl-3-methyl-4-acylpyrazol-5-ones . J. Chem. Soc., Dalton Trans. 2002 , 1409 – 1415 .
  • Londershausen , M. Review: Approaches to new parasiticides . Pestic. Sci. 1996 , 48 , 269 – 292 .
  • Singh , D. ; Singh , D. Synthesis and antifungal activity of some 4-arylmethylene derivatives of substituted pyrazolones . J. Indian Chem. Soc. 1991 , 68 , 165 – 167 .
  • Lubs , H. A. The Chemistry of Synthetic Dyes and Pigments ; American Chemical Society : Washington , DC , 1970 .
  • Wisniewski , M. Z. ; Surga , W. J. ; Opozda , E. M. Palladium(II) methylpyrazole complexes . Transition Met. Chem. 1994 , 19 , 353 – 354 .
  • Hamama , W. S. Pyrazolones as versatile precursors for the synthesis of fused and binary heterocycles . Synth. Commun. 2001 , 31 , 1335 – 1345 .
  • Li , X.-L. ; Wang , Y.-M. ; Tian , B. ; Matsuura , T. ; Meng , J.-B. The solid-state Michael addition of 3-methyl-1-phenyl-5-pyrazolone . J. Heterocycl. Chem. 1998 , 35 , 129 – 134 .
  • Singh , D. ; Singh , D. Synthesis of 1,3-disubstituted 4-arylidenepyrazolin-5-ones and the keto and enol forms of 4,4′-arylidenebis(1,3-disubstituted pyrazolin-5-ones) . J. Chem. Eng. Data 1984 , 29 , 355 – 356 .
  • Mitra , A. S. ; Rout , M. K. Tautomeric products of condensation of aromatic aldehydes . J. Indian Chem. Soc. 1961 , 38 , 893 – 895 .
  • Pavlov , P. T. ; Goleneva , A. F. ; Lesnov , A. E. ; Prokhorova , T. S. Biological activity of some pyrazolone derivatives . Pharm. Chem. J. (Engl. Trans.) 1998 , 32 , 370 – 372 .
  • Wang , W. ; Wang , S.-X. ; Qin , X.-Y. ; Li , J.-T. Reactions of the aldehydes and pyrazolones ion in the presence of sodium dodecyl sulfate in aqueous media. Synth. Commun. 2005, 35, 1263–1269.
  • Elinson , M. N. ; Dorofeev , A. S. ; Nasybullin , R. F. ; Nikishin , G. I. Facile and convenient synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) by electrocatalytic tandem Knovenagel–Michael reaction . Synthesis 2008 , 12 , 1933 – 1937 .
  • Sujatha , K. ; Shanthi , G. ; Selvam , N. P. ; Manoharan , S. ; Perumal , P. T. ; Rajendran , M. Synthesis and antiviral activity of 4,4′ (arylmethylene)bis(1H-pyrazol-5-ols) against peste des petits ruminant virus (PPRV) . Bioorg. Med. Chem. Lett. 2009 , 19 , 4501 – 4503 .
  • Niknam , K. ; Saberi , D. ; Sadegheyan , M. ; Deris , A. Silica-bonded S-sulfonic acid: An efficient and recyclable solid acid catalyst for the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) . Tetrahedron Lett. 2010 , 51 , 692 – 694 .
  • Okuhara , T. ; Mizuno , N. ; Misono , M. Catalytic chemistry of heteropoly compounds . Adv. Catal. 1996 , 41 , 113 – 252 .
  • (a) Tiofeeva , M. N. ; Dimidov , A. V. ; Kozhevnikov , I. V. UV-Vis and ESR spectroscopic studies of the adsorption of arenes on the heteropoly acid H3PW12O40 . J. Mol. Catal. 1993 , 79 , 21 – 28 . (b) Chaskar , A. ; Padalkar , V. ; Phatangare , K. ; Langi , B. ; Naik , P. Phosphomolybdic acid–catalyzed highly efficient and simple one-pot synthesis of quinoxaline . J. Korean Chem. Soc. 2009 , 53 , 727 – 730 . (c) Chaskar , A. ; Padalkar , V. ; Phatangare , K. ; Langi , B. ; Shah , C. Miceller-mediated phosphomolybdic acid: Highly effective reusable catalyst for synthesis of quinoline and its derivatives . Synth. Commun. 2010 , 40 , 2336 – 2340 .
  • (a) Drago , R. S. ; Dias , J. A. ; Maier , T. Acidity scale for Brønsted acids including H3PW12O40 . J. Am. Chem. Soc. 1997 , 119 , 7702 – 7710 . (b) Chaskar , A. ; Padalkar , V. ; Phatangare , K. ; Patil , K. ; Bodkhe , A. ; Langi , B. Heteropoly acids as useful recyclable heterogenous catalyst for the facile and highly efficient aza-Cope rearrangement of N-allylanilines . Appl. Catal A: Gen. 2009 , 359 , 84 – 87 . (c) Gawand , P. ; Deokar , H. ; Langi , B. ; Yadav , A. ; Chaskar , A. H3Mo12O40P-catalyed one-pot synthesis of amidoalkyl naphthols . Synth. Commun. 2009 , 39 , 4171 – 4179 .
  • Schwegler , M. A. ; Van Bekkum , H. ; Munck , N. Heteropolyacids as catalysts for the production of phthalate diesters . Appl. Catal. 1991 , 74 , 191 – 204 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.