Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 10
553
Views
16
CrossRef citations to date
0
Altmetric
Original Articles

Sulfamic Acid (H2NSO3H): A Low-Cost, Mild, and Efficient Catalyst for the Synthesis of Substituted N-Phenylpyrazoles Under Solvent-Free Conditions

&
Pages 1411-1418 | Received 29 Jun 2010, Published online: 25 Jan 2012

REFERENCES

  • Polshettiwar , V.; Varma R. S. Greener and rapid access to bio-active hetrocycles: Room-temperature synthesis of pyrazoles and diazepines in aqeuous medium . Tetrahedron Lett. 2008 , 49 , 397 – 400 .
  • Reddy , A. R. ; Sampath , A. ; Reddy , P. P. An improved and scalable process for celecoxib: A selective cyclooxgenase-2 inhibitor . Org. Process Res. Dev. 2009 , 13 , 98 – 101 .
  • Jeannin , P. N-Phenylpyrazole based antiflea and antitick external device for cats and dogs. U.S. Patent 5,885,607, March 23, 1999.
  • (a) Wang , Z. ; Qin , H. Solventless syntheses of pyrazole derivatives . Green Chem. 2004 , 6 , 90 – 92 ; (b) Polshettiwar , V. ; Varma , R. S. Greener and rapid access to bio-active hetrocycles: Room-temperature synthesis of pyrazoles and diazepines in aqeuous medium . Tetrahedron Lett. 2008 , 49 , 397 – 400 .
  • (a) Heller , S. T. ; Natarajan , S. R. 1,3-Diketones from acid chlorides and ketones: A rapid and one-pot synthesis of pyrazoles . Org. Lett. 2006 , 8 , 2675 – 2678 ; (b) Mohamed Ahmed , M. S. ; Kobayashi , K. ; Mori , A. One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling . Org. Lett. 2005 , 7 , 4487 – 4489 ; (c) Deng , X. ; Mani , N. S. Base-mediated reaction of hydrazones and nitroolefins with a reversed regioselectivity: A novel synthesis of 1,3,5-trisubstituted pyrazoles . Org. Lett. 2008 , 10 , 1307 – 1310 ; (d) Deng , X. ; Mani , N. S. Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles from N-arylhydrazones and nitrooeofins . J. Org. Chem. 2008 , 73 , 2412 – 2415 ; (e) Martin , R. ; Rivero , M. R. ; Buchwald , S. L. Domino Cu-catalyzed C-N coupling/hydroamidation: A highly efficient synthesis of nitrogen heterocycles . Angew. Chem. Int. Ed. 2006 , 45 , 7079 – 7082 .
  • Chen , X. ; She , J. ; Shang , Z. ; Wu , J. ; Wu , H. ; Zhang , P. Synthesis of pyrazoles, diazepines, enaminones and enamino esters using 12-tungstophophoric acid as a reusable catalyst in water . Synthesis 2008 , 21 , 3478 – 3486 .
  • Chen , X. ; She , J. ; Shang , Z. ; Wu , J. ; Zhang , P. Room-temperature synthesis of pyrazoles, diazepines, β-enaminones, and β-enamino esters using silica-supported sulfuric acid as a reusable catalyst under solvent-free conditions . Synth. Commun. 2009 , 39 ( 6 ), 947 – 957 .
  • Sreekumar , R. ; Padmakumar , R. Simple, efficient, and convenient synthesis of pyroles and pyrazoles using zeolites . Synth. Commun. 1998 , 28 ( 9 ), 1661 – 1665 .
  • Texier-Boulett , F. ; Klein , B. ; Hamelin , J. Pyrole and pyrazole ring closure in heterogeneous media . Synthesis 1986 , 409 – 411 .
  • (a) Singh , P. R. ; Singh , D. U. ; Samant , S. D. Sulphamic acid: An efficient and cost-effective acid catalyst for the Pechmannn reaction. Synlett 2004, 11, 1909–1912; (b) Singh , P. R. ; Singh , D. U. ; Samant , S. D. Sulphamic acid: A mild, efficient, and cost-effective acid catalyst for the synthesis of bis(1H-indol-3-yl)methanes. Synth. Commun. 2005, 35(16), 2133–2138.
  • Penicillins: Beecham Group Ltd., GB952283, 1963; Chem. Abstr. 1964, 61, 8315d.
  • Vogel , A. I. ; Tatchell , A. R. Vogel's Textbook of Practical Organic Chemistry, , 4th ed. ; ELBS/Longman , UK , 1978 ; p. 882 .

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.