Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
287
Views
22
CrossRef citations to date
0
Altmetric
Original Articles

Sulfamic Acid as a Novel, Efficient, Cost‐Effective, and Reusable Solid Acid Catalyst for the Synthesis of Pyrroles under Solvent‐Free Conditions

Pages 803-809 | Received 13 Sep 2007, Published online: 15 Feb 2008

References

  • Sundberg , R. A. 1984 . Comprehensive Heterocyclic Chemistry Edited by: Katritzky , A. and Rees , C. W. Vol. 4 , 329 Oxford : Pergamon .
  • Lainton , J. , Hoffman , J. W. , Martin , B. R. and Compton , D. R. 1995 . 1‐Alkyl‐3‐(1‐naphthoyl)pyrroles: a new class of cannabinoid . Tetrahedron Lett. , 36 : 1401 – 1403 .
  • Rango , R. , Marshal , G. R. , Di Santo , R. , Costi , R. , Rompei , S. and Artico , M. 2000 . Antimycobacterial pyrroles: synthesis, anti‐Mycobacterium tuberculosis activity and QSAR studies . Bioorg. Med. Chem. , 8 : 1423 – 1432 .
  • Manning , A. R. and Davis , D. J. 2003 . Targetting JNK for therapeutic benefit: from junk to gold? . Nature Rev., Drug Discovery , 2 : 554 – 565 .
  • De Leo , C. Y. and Ganem , B. 1997 . A new approach to porphobilinogen and its analogs . Tetrahedron , 53 : 7731 – 7752 .
  • Gilchrist , T. L. 1998 . Synthesis of aromatic heterocycles . J. Chem. Soc., Perkin Trans. 1 , : 615 – 628 .
  • Hantzsch , A. 1890 . Pyrrole synthesis . Ber. Dtsch. Chem. Ges. , 23 : 1474
  • Trautwein , A. W. , Submuth , R. D. and Jung , G. 1998 . Hantzsch pyrrole synthesis on solid support . Bioorg. Med. Chem. Lett. , 8 : 2381
  • Knorr , L. 1884 . Synthesis of pyrroles . Ber. Dtsch. Chem. Ges. , 17 : 1635
  • Alberola , A. , Ortega , A. G. , Sadaba , M. L. and Sanudo , C. 1999 . Versatility of Weinreb amides in the Knorr pyrrole synthesis . Tetrahedron , 55 : 6555 – 6566 .
  • Katritzky , A. R. , Jiang , J. and Steel , P. J. 1994 . A novel CHCH‐N synthom . J. Org. Chem. , 59 : 4551 – 4556 .
  • Paal , C. 1885 . Ber. Dtsch. Chem. Ges. , 18 : 367
  • Jones , R. A. and Been , R. G. P. 1977 . The Chemistry of Pyrroles 3 New York : Academic Press .
  • Chiu , P. K. and Sammes , M. P. 1990 . The synthesis and chemistry of azolenines, part 18: preparation of 3‐ethoxycarbonyl‐3‐pyorrole via Paal–Knorr reaction, and sigmatropic rearrangements involving competitive ester migrations to c‐2, c‐4 and n . Tetrahedron , 46 : 3439 – 3456 .
  • Yu , S. X. and Quesne , P. W. 1995 . Metabolites, 3: total synthesis of (±)‐funebral, a rotationally restricted pyrrole alkaloid, using a novel Paal–Knorr reaction . Tetrahedron Lett. , 36 : 6205 – 6208 .
  • Ballini , R. , Barboni , Bosica , G. and Petrini , M. 2000 . 2,5‐Dialkylfurans and nitroalkanes as source of 2,3,5‐trialkylpyrroles . Synlett , : 391 – 393 .
  • Banik , B. K. , Renteria , M. and Dasgupta , S. K. 2005 . A straightforward highly efficient Paal–Knorr synthesis of pyrroles . Tetraheron Lett. , 46 : 2643 – 2645 .
  • Yadav , J. S. , Reddy , B. V. , Eeshwaraiah , B. and Gupta , M. K. 2004 . Bi(OTf)3/[bmim]BF4 as novel and reusable catalytic system for the synthesis of furan, pyrrole and thiophene derivatives . Tetraheron Lett. , 45 : 5873
  • Chen , J. , Wu , H. , Zheng , Z. , Jin , C. , Zhang , X. and Su , W. 2006 . An approach to the Paal–Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent‐free conditions . Tetrahedron Lett. , 47 : 5383 – 5387 .
  • Banik , B. K. , Samajdar , S. and Banik , I. 2004 . Simple synthesis of pyrroles . J. Org. Chem. , 69 : 213 – 216 .
  • Wang , B. , Gu , Y. , Luo , C. , Yang , T. , Yang , L. and Suo , J. 2004 . Pyrrole synthesis in ionic liquids by Paal–Knorr condensation under mild conditions . Tetrahedron Lett. , 45 : 3417
  • Curini , M. , Montanari , F. , Rosati , O. , Lioy , E. and Margarita , R. 2003 . Layered zirconium phosphate and phosphonate as heterogeneous catalyst in the preparation of pyrroles . Tetrahedron Lett. , 44 : 3923
  • Clark , J. H. 2002 . Solid acids for green chemistry . Acc. Chem. Res. , 35 : 791 – 797 .
  • Li , J. T. , Han , J. F. , Yang , J. H. and Li , T. S. 2003 . Solid acid in organic synthesis . Ultrason. Sonochem. , 10 : 119 – 125 .
  • Yadav , J. S. , Rao , P. , Sreenu , D. , Rao , R. S. , Kumar , V. N. , Nagaiah , K. and Prasad , A. R. 2005 . Sulfamic acid: an efficient, cost‐effective and recyclable solid acid catalyst for the Friedlander quinoline synthesis . Tetrahedron Lett. , 46 : 7249 – 7252 .
  • Heydari , A. , Khaksar , S. , Pourayoubi , M. and Mehjoub , A. R. 2007 . Sulfamic acid: an efficient, cost‐effective and recyclable solid acid catalyst for the three‐component synthesis of α‐amino nitriles . Tetrahedron Lett. , 48 : 4059 – 4061 .
  • Tao , L. , Zou , J. , Zhang , L. L. and Zhang , Y. 2007 . Sulfamic acid‐catalyzed Michael addition of indoles and pyrrole to electron‐deficient nitroolefins under solvent‐free condition . Tetrahedron Lett. , 48 : 4297 – 4299 .
  • De , S. K. 2004 . Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines . Tetrahedron Lett. , 45 : 2919
  • De , S. K. and Gibbs , R. A. 2004 . Bismuth trichloride catalyzed synthesis of α‐aminonitriles . Tetrahedron Lett. , 45 : 7404 – 7407 .
  • De , S. K. and Gibbs , R. A. 2005 . A mild and efficient one‐step synthesis of quinolines . Tetrahedron Lett. , 45 : 1647 – 1649 .
  • De , S. K. and Gibbs , R. A. 2005 . Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5‐benzodiazepine derivatives . Tetrahedron Lett. , 46 : 1811 – 1813 .
  • Royer , L. , De , S. K. and Gibbs , R. A. 2005 . Iodine as a novel and efficient reagent for the synthesis of α‐aminonitriles by a three‐component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide . Tetrahedron Lett. , 46 : 4595 – 4597 .
  • Donelson , J. L. , Gibbs , R. A. and De , S. K. 2006 . J. Mol. Cat. A , 256 : 309

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.