Jundishapur Journal of Natural Pharmaceutical Products

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Marine Sponge/H3PO4: As a Naturally Occurring Chiral Catalyst for Solvent-free Fischer-Indole Synthesis

Mohammad Reza Shushizadeh 1 , 2 , * , Azar Mostoufi 1 , Rashid Badri 3 and Somaye Azizyan 3
Authors Information
1 Department of Medicinal Chemistry, Ahvaz Jundishahpur University of Medical Sciences, Ahvaz, IR Iran
2 Marine Pharmaceutical Science Research Center, Ahvaz Jundishapur University of Medical Sciences, IR Iran
3 Islamic Azad University-Khoozestan Science and Research Center, Ahvaz, IR Iran
Article information
  • Jundishapur Journal of Natural Pharmaceutical Products: November 1, 2013, 8 (4); 160-164
  • Published Online: November 1, 2013
  • Article Type: Research Article
  • Received: April 26, 2013
  • Revised: May 27, 2013
  • Accepted: June 15, 2013
  • DOI: 10.17795/jjnpp-11804

To Cite: Shushizadeh M R, Mostoufi A, Badri R, Azizyan S. Marine Sponge/H3PO4: As a Naturally Occurring Chiral Catalyst for Solvent-free Fischer-Indole Synthesis, Jundishapur J Nat Pharm Prod. 2013 ; 8(4):160-164. doi: 10.17795/jjnpp-11804.

Copyright © 2013, School of Pharmacy, Ahvaz Jundishapur University of Medical Sciences. This is an open-access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/) which permits copy and redistribute the material just in noncommercial usages, provided the original work is properly cited.
1. Background
2. Objectives
3. Materials and Methods
4. Results
5. Discussion
  • 1. Humphrey GR, Kuethe JT. Practical methodologies for the synthesis of indoles. Chem Rev. 2006; 106(7): 2875-911[DOI][PubMed]
  • 2. Gribble GW. Recent developments in indole ring synthesis—Methodology and applications. J Chem Soci Perkin Trans. 2000; (7): 1045-75
  • 3. Sundberg RJ. Indoles (Best Synthetic Methods). 1996;
  • 4. Inman M, Moody CJ. A two step route to indoles from haloarenes--a versatile variation on the Fischer indole synthesis. Chem Commun (Camb). 2011; 47(2): 788-90[DOI][PubMed]
  • 5. Ashcroft CP, Hellier P, Pettman A, Watkinson S. Second-Generation Process Research Towards Eletriptan: A Fischer Indole Approach. Org Proc Res Dev. 2010; 15(1): 98-103[DOI]
  • 6. Wahab B, Ellames G, Passey S, Watts P. Synthesis of substituted indoles using continuous flow micro reactors. Tetrahedron. 2010; 66(21): 3861-5[DOI]
  • 7. Jiang H, Wang Y, Wan W, Hao J. p-TsOH promoted Fischer indole synthesis of multi-substituted 2-trifluoromethyl indole derivatives. Tetrahedron. 2010; 66(14): 2746-51[DOI]
  • 8. Xu DQ, Wu J, Luo SP, Zhang JX, Wu JY, Du XH, et al. Fischer indole synthesis catalyzed by novel SO3H-functionalized ionic liquids in water. Green Chem. 2009; 11(8): 1239-46[DOI]
  • 9. Park IK, Suh SE, Lim BY, Cho CG. Aryl hydrazide beyond as surrogate of aryl hydrazine in the Fischer indolization: the synthesis of N-Cbz-indoles, N-Cbz-carbazoles, and N,N'-bis-Cbz-pyrrolo[2,3-f]indoles. Org Lett. 2009; 11(23): 5454-6[DOI][PubMed]
  • 10. Jeanty M, Blu J, Suzenet F, Guillaumet G. Synthesis of 4- and 6-azaindoles via the Fischer reaction. Org Lett. 2009; 11(22): 5142-5[DOI][PubMed]
  • 11. Sudhakara A, Jayadevappa H, Mahadevan KM, Hulikal V. Efficient synthesis of 2-ethoxycarbonyl indoles. Synth Commun. 2009; 39(14): 2506-15[DOI]
  • 12. Varma PP, Sherigara BS, Mahadevan KM, Hulikal V. Efficient and straightforward synthesis of tetrahydrocarbazoles and 2, 3-dimethyl indoles catalyzed by CAN. Synth Commun. 2008; 39(1): 158-65[DOI]
  • 13. Chen J, Chen W, Hu Y. Microwave-Enhanced Fischer Reaction: An Efficient One-Pot Synthesis of γ-Carbolines. Synlett. 2008; 2008(1): 77-82
  • 14. Xu DQ, Yang WL, Luo SP, Wang BT, Wu Jian, Xu ZY. Fischer indole synthesis in brønsted acidic ionic liquids: a green, mild, and regiospecific reaction system. Eur J Org Chem. 2007; 2007(6): 1007-12[DOI]
  • 15. Robinson B, Robinson B. The Fischer indole synthesis. 1982;
  • 16. Kissman HMF, Farnsworth DW, Witkop B. Fischer indole syntheses with polyphosphoric acid. J Am Chem Soci. 1952; 74(15): 3948-9
  • 17. Bratulescu G. A new and efficient one-pot synthesis of indoles. Tetrahedron Let. 2008; 49(6): 984-6[DOI]
  • 18. Yi FP, Sun HY, Pan XH, Xu Y, Li JZ. Synthesis of Fischer indole derivatives using carboxyl-functionalized ionic liquid as an efficient and recyclable catalyst. Chin Chem Let. 2009; 20(3): 275-8[DOI]
  • 19. Chaskar A, Deokar H, Padalkar V, Phatangare K, Patil SK. Highly Efficient and Facile Green Approach for One-Pot Fischer Indole Synthesis. J Korean Chem Soci. 2010; 54(4): 411-3[DOI]
  • 20. Desroses M, Wieckowski K, Stevens M, Odell LR. A microwave-assisted, propylphosphonic anhydride (T3P®) mediated one-pot Fischer indole synthesis. Tetrahedron Let. 2011; 52(34): 4417-20[DOI]
  • 21. Rifai S, Fassouane A, El-Abbouyi A, Wardani A, Kijjoa A, Van Soest R. Screening of antimicrobial activity of marine sponge extracts. J Med Mycol. 2005; 15(1): 33-8[DOI]
  • 22. McCaffrey EJ, Endean R. Antimicrobial activity of tropical and subtropical sponges. Marine Biol. 1985; 89(1): 1-8[DOI]
  • 23. Shushizadeh MR, Mostoufi A, Fakhrian M. Marine Sponge/CuO Nanocrystal: A Natural and Efficient Catalyst for Sulfonamides Synthesis. Jundishapur J Nat Pharm Prod. 2012; 7(4): 134-9
  • 24. Sarma NS, Krishna M, Rao SR. Sterol ring system oxidation pattern in marine sponges. Marine Drugs. 2005; 3(3): 84-111[DOI]
  • 25. Hughes DL. Progress in the Fischer indole reaction. A review. Org Prep Proced Int. 1993; 25(6): 607-32[DOI]
  • 26. Przheval'skii NM, Kostromina LY, Grandberg II. Mechanism of Fischer reaction. Dependence of thermal indolization of cyclohexanone arylhydrazones on nature of substituent in the benzene ring. Chem Heterocycl Comp. 1988; 24(2): 154-8
  • 27. Dhakshinamoorthy A, Pitchumani K. Facile clay-induced Fischer indole synthesis: A new approach to synthesis of 1, 2, 3, 4-tetrahydrocarbazole and indoles. Appl Catal A Gen. 2005; 292: 305-11[DOI]
  • 28. Chen J, Hu Y. Microwave Assisted One‐Pot Synthesis of 1, 2, 3, 4‐Tetrahydrocarbazoles. Synth Commun. 2006; 36(11): 1485-94[DOI]
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