Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 16
290
Views
34
CrossRef citations to date
0
Altmetric
Original Articles

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

&
Pages 2382-2387 | Received 23 Nov 2010, Published online: 14 May 2012

REFERENCES

  • Elguero , J. Pyrazoles. In Comprehensive Heterocyclic Chemistry II ; A. R. Katritzky , C. W. Rees , and E. F. V. Scriven , (Eds.); Pergamon : Oxford , UK , 1996 ; vol. 3 , pp. 1 – 76 .
  • 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 . 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 , (Eds.); Interscience : New York , 1967 .
  • Rosiere , C. E. ; Grossman , M. I. An analog of histamine that stimulates gastric acid secretion without other actions of histamine . Science 1951 , 113 , 651 .
  • 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. Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate . J. Indian Chem. Soc. 1991 , 68 , 245 – 246 .
  • Chauhan , P. M. S. ; Singh , S. ; Chatterjee , R. K. Antimalarial profile of substituted pyrazoles: A new class of antimalarial agents . Indian J. Chem., Sect. B 1993 , 32 , 858 – 861 .
  • Djuric , S. W. ; Bmaung , N. Y. ; Basha , A. ; Liu , H. ; Luly , J. R. ; Madar , D. J. ; Sciotti , R. J. ; Tu , N. P. ; Wagenaar , F. L. ; Wiedman , P. E. ; Zhou , X. ; Ballaron , S. ; Bauch , J. ; Chen , Y.- W. ; Chiou , X. G. ; Fey , T. ; Gauvin , D. ; Gubbins , E. ; Hsieh , G. C. ; Marsch , K. C. ; Mollison , K. W. ; Pong , M. ; Shaughnessy , T. K. ; Sheets , M. P. ; Smith , M. ; Trevillyan , J. M. ; Warrior , U. ; Wegner , C. D. ; Carter , G. W. 3,5-Bis(trifluoromethyl)pyrazoles: A novel class of NFAT transcription factor regulator . J. Med. Chem. 2000 , 43 , 2975 .
  • Chimenti , F. ; Maccioni , E. ; Secci , D. ; Bolasco , A. ; Chimenti , P. ; Granese , A. ; Befani , O. ; Turini , P. ; Alcaro , S. ; Ortuso , F. ; Cirilli , R. ; La Torre , F. ; Cardia , M. C. ; Simona , D. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazole derivatives . J. Med. Chem. 2005 , 48 , 7113 .
  • 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. J. The solid-state Michael addition of 3-methyl-1-phenyl-5-pyrazolone. J. Heterocycl. Chem. 1998, 35, 129–134.
  • Singh , D. ; Singh , D. Syntheses of 1,3-disubstituted 4-arylidenepyrazolin-5-ones and the keto and enol forms of 4,40-arylidenebis(1,3-disubstituted pyrazolin-5-ones) . J. Chem. Eng. Data 1984 , 29 , 355 – 356 .
  • 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 .
  • Buzykin , B. I. ; Lonshchakova , T. I. Reaction of azines with 5-pyrazolones . Bull. Acad. Sci. USSR. 1971 , 2224 – 2226 .
  • Wang , W. ; Wang , S.-X. ; Qin , X.-Y. ; Li , J.-T. Reaction of aldehydes and pyrazolones in the presence of sodium dodecyl sulfate in a queous 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 Knoevenagel–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 .
  • Sargent , E. V. ; Adolph , J. ; Clemmons , M. K. ; Kirk , G. D. ; Pena , B. M. ; Fedoruk , M. J. Evaluation of flu-like symptoms in workers handling xanthan gum powder , J. Occup. Med. 1990 , 32 , 625 .
  • Davidson , R. L. (Ed.). Handbook of Water-Soluble Gums and Resins ; McGraw-Hill : 1980 .
  • Whistler , R. L. ; BeMiller , J. N. (Eds.). Industrial Gums: Polysaccharides and Their Derivatives ; Academic Press : 1973 .
  • Shaabani , A. ; Maleki , A. ; Soudi , M. R. ; Mofakham , H. Xanthan sulfuric acid: A new and efficient biosupported solid acid catalyst for the synthesis of α-amino nitriles by condensation of carbonyl compounds, amines, and trimethylsilylcyanide . Catal. Commun. 2009 , 10 , 945 .
  • (a) Venu Madhav , J. ; Thirupathi Reddy , Y. ; Narsimha Reddy , P. ; Nikhil Reddy , M. ; Suresh , K. ; Crooks , P. A. ; Rajitha , B. Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl- 14H-dibenzo[a.j]xanthenes under solvent-free conditions . J. Mol. Catal. A 2009 , 304 , 85 – 87 ; (b) Venu Madhav , J. ; Suresh Kuarm , B. ; Rajitha , B. Dipyridine cobalt chloride: A novel and efficient catalyst for the synthesis of aryl-4H-dibenzo[a.j]xanthenes under solvent-free conditions . Arkivoc , 2008 , 12 , 204 ; (c) Venu Madhav , J. ; Suresh Kuarm , B. ; Someshwar , P. ; Rajitha , B. Thirupathi Reddy , Y. ; Crooks , P. A. CuPy2Cl2: A novel and efficient catalyst for synthesis of propargylamines under conventional method and microwave irradiation . Synth. Commun 2008 , 38 , 3215 ; (d) Venu Madhav , J. ; Suresh Kuarm , B. ; Rajitha , B. The solid-state synthesis of 1,3-selenazoles by employing the CuPy2Cl2 as a Lewis acid catalyst . Synth. Commun. 2008 , 38 , 3514 – 3522 ; (e) Venu Madhav , J. ; Suresh Kuarm , B. ; Rajitha , B. Dipyridine copper chloride as a mild and efficient catalyst for the solid-state synthesis of 2-substituted benzimidazoles . Arkivoc 2008 , 13 , 145 – 150 (f) Venu Madhav , J. ; Suresh Kuarm , B. ; Someshwar , P. ; Rajitha , B. Thirupathi Reddy , Y. ; Crooks , P. A. Dipyridine cobalt chloride: A novel catalyst for the synthesis of coumarins via Pechmann condensation . J. Chem. Res. 2008 , 232 – 234 ; (g) Suresh Kuarm , B. ; Venu Madhav , J. ; Vijaya Laxmi , S. ; Rajitha , B. ; Thirupathi Reddy , Y. ; Narsimha Reddy , P. ; Crooks , P. A. An expeditious Pechmann condensation by using biodegradable cellulose sulfuric acid as a solid acid catalyst . Synth. Commun. 2010 , 40 , 3358 ; (h) Suresh Kuarm , B. ; Thirupathi Reddy , Y. ; Venu Madhav , J. ; Crooks , P. A. ; Rajitha , B. 3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents . Bioorg. Med. Chem. Lett. 2011 , 21 , 524 – 527 .
  • Niknam , K. ; Saberi , D. ; Sadegheyan , M. ; Deris , A. Silica-bonded S-sulfonic acid: An efficient and recyclable solid acid catalystfor the synthesis of 4,4′-(arylmethylene)bis(1H- pyrazol-5-ols) . Tetrahedron Lett. 2010 , 51 , 692 – 694 .

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.