Advanced search
Publication Cover
Supramolecular Chemistry Volume 26, 2014 - Issue 10-12
Submit an article Journal homepage
178
Views
6
CrossRef citations to date
0
Altmetric
Articles

Supramolecular catalysis in the synthesis of polyfunctionalised pyrroles

Shyam Babu SinghEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Pankaj Kumar VermaEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Kamleshwar TiwariEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Madhulika SrivastavaEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Preyas AnkitEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Mandavi SinghEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
,
Jagdamba SinghEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, IndiaCorrespondence[email protected]
&
Kamla Prasad TiwariEnvironmentally Benign Synthesis Laboratory, Department of Chemistry, University of Allahabad, Allahabad211002, India
 show all
Pages 882-889 | Received 22 Jul 2013, Accepted 16 Dec 2013, Published online: 24 Mar 2014

References

  • (a) Sundberg, R.J. In Comprehensive Heterocyclic Chemistry II: Fan, W.Q., Katritzky, A.R., Rees, C.W., Scriven, E.F.V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, p 149; (b) Black, D. In STC: Science of Synthesis: George, M.G., Ed.; 1H-Pyrroles, Thieme: Stuttgart, 2001; Vol. 9, pp 441–552.
  • (a) Gottesfeld, J.M.; Neely, L.; Trauger, J.W.; Baird, E.E.; Dervan, P.B. Nature1997, 387, 202–205; (b) Lewer, P.; Chapin, W.L.; Graupner, P.R.; Gilbert, J.R.; Peacock, C. J. Nat. Prod.2003, 66, 143–145; (c) Fuerstner, A. Angew. Chem. Int. Ed.2003, 42, 3582–3603; (d) Fürstner, A. Angew. Chem.2003, 115, 3706–3728; (e) Balme, G. Angew. Chem.2004, 116, 6396–6399; Angew. Chem. Int. Ed.2004, 43, 6238–6240; (f) Agarwal, S.; Cämmerer, S.; Filali, S.; Fröhner, W.; Knöll, J.; Krahl, M.P.; Reddy, K.R.; Knölker, H.J. Curr. Org. Chem. 2005, 9, 1601–1614; (g) Jacquot, D.E.N.; Zöllinger, M.; Lindel, T. Angew. Chem.2005, 117, 2336–2338; Angew. Chem. Int. Ed.2005, 44, 2295–2298; (h) Garrido-Hernandez, H.; Nakadai, M.; Vimolratana, M.; Li, Q.; Doundoulakis, T.; Harran, P.G. Angew. Chem.2005, 117, 775–779; Angew. Chem. Int. Ed.2005, 44, 765–769; (i) Walsh, C.T.; Garneau-Tsodikova, S.; Howard-Jones, A.R. Nat. Prod. Rep.2006, 23, 517–531; (j) Grube, A.; Kock, M. J. Nat. Prod.2006, 69, 1212–1214; (k) Aiello, A.; D'Esposito, M.; Fattorusso, E.; Menna, M.; Mueller, W.E.G.; Perovic-Ottstadt, S.; Schroeder, H.C. Bioorg. Med. Chem.2006, 14, 17–24; (l) Trost, B.M.; Dong, G. Org. Lett.2007, 9, 2357–2579; (m) Fan, H.; Peng, J.; Hamann, M.T.; Hu, J.-F. Chem. Rev.2007, 108, 264–287; (n) Grube, A.; Köck, M. Org. Lett.2006, 8, 4675–4678; (o) Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; Van Soest, R.V.M.; Fusetani, N. J. Am. Chem. Soc.2003, 125, 15700–15701; (p) Fürstner, A. Angew. Chem. Int. Ed.2003, 42, 3582–3603; (q) Boger, D.L.; Boyce, C.W.; Labroli, M.A.; Sehon, C.A.; Jin, Q. J. Am. Chem. Soc.1999, 121, 54–62.
  • Lohray, B.B.; Lohray, V.Pure Appl. Chem.2005, 77, 179–184.
  • (a) Berlin, A.; Vercelli, B.; Zotti, G. Polym. Rev.2008, 48, 493–530; (b) Gabriel, S.; Cécius, M.; Fleury-Frenette, K.; Cossemen, D.; Hecq, M.; Ruth, N.; Jérôme, R.; Jérôme, C. Chem. Mater.2007, 19, 2364–2371; (c) Novák, P.; Müller, K.; Santhanam, K.S.V.; Haas, O. Chem. Rev.1997, 97, 207–282.
  • (a) Daidone, G.; Maggio, B.; Schillari, D. Pharmazie1990, 45, 441–442; (b) Kimura, T.; Kawara, A.; Nakao, A.; Ushiyama, S.; Shimozato, T.; Suzuki, K. PCT Int. Appl. WO 0001688 A1 20000113, 2000; (c) Kaiser, D.G.; Glenn, E.M. J. Pharm. Sci.1972, 61, 1908–1911; (d) Demir, A.S.; Akhmedov, I.M.; Sesenoglu, O. Tetrahedron2002, 58, 9793–9799; (e) Meshram, H.M.; Prasad, B.R.V.; Kumar, D.A. Tetrahedron Lett.2010, 51, 3477–3478; (f) Davis, F.A.; Bowen, K.A.; Xu, H.; Velvadapu, V. Tetrahedron2008, 64, 4174–4182.
  • (a) Jones, R.A.; Bean, G.P. The Chemistry of Pyrroles; Academic Press: London, 1977; p 1; (b) Sundberg, R.J. In Comprehensive Heterocyclic Chemistry: Katritzky, A.R., Rees, C.W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, p 370; (c) Sundberg, R.J. In Comprehensive Heterocyclic Chemistry II: Katritzky, A.R., Rees, C.W., Scriven, E.F.V., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, p 149; (d) Boger, D.L.; Boyce, C.W.; Labroli, M.A.; Sehon, C.A.; Jin Q. J. Am. Chem. Soc.1999, 121, 54–62; (e) Gupton, J.T. Top. Heterocycl. Chem.2006, 2, 53–92; (f) Fan, H.; Peng, J.; Hamann, M.T.; Hu, J.-F. Chem. Rev.2008, 108, 264–287; (g) Reisser, M.; Maas, G. J. Org. Chem.2004, 69, 4913–4924.
  • Katritzky, A.R.; Huang, T.B.; Voronkov, M.; Wang, M.; Kolb, H.J. Org. Chem.2000, 65, 8819–8821.
  • (a) Finar, I.L. Organic Chemistry Stereochemistry and Chemistry of Natural Products; Longman: London, 1975; 5th ed., Vol. 2, pp 885–913; (b) Boger, D.L.; Boyce, C.W.; Labroli, M.A.; Sehon, C.A.; Jin, Q. J. Am. Chem. Soc.1999, 121, 54–62; (c) Abid, M.; Landge, S.M.; Török, B. Org. Prep. Proced. Int.2006, 38, 495–500.
  • (a) Fuerstner, A. Synlett1999, 1523–1533; (b) Higgins, S.J. Chem. Soc. Rev.1997, 26 (10), 247–258; (c) McCullough, R.D.; Ewbank, P.C. In Handbook of Conducting Polymers Skotheim: T.A., Elsenbaumer, R.L., Reynolds, J.R., Dekker M., Eds.; CRC Press: New York, 2nd ed. 1998; Chapter 9, pp 225–258; (d) Curran, D.; Grimshaw, J.; Perera, S.D. Chem. Soc. Rev. CRC Press, 1991, 20, 391–404; (e) Deronzier, A.; Moutet, J.C. Curr. Top. Electrochem.1994, 3, 159–200; (f) Kros, A.; Nolte, R.J.M.; Sommerdijk, N.A.J.M. Adv. Mater.2002, 14, 1779–1782; (g) Facchetti, A.; Abbotto, A.; Beverina, L.; Vander Boom, M.E.; Dutta, P.; Evmenenko, G.; Pagani, G.A.; Marks, T.J. Chem. Mater.2003, 15, 1064–1072; (h) Guernion, N.J.L.; Hayes, W. Curr. Org. Chem.2004, 8, 637–651. (i) Pu, S.; Liu, G.; Shen, L.; Xu, J. Org. Lett.2007, 9, 2139–2142.
  • (a) Knorr, L. Chem. Ber.1884, 17, 1635–1642; (b) Paal, C. Chem. Ber. 1885, 18, 367–371; (c) Amarnat, V.; Anthony, D.C.; Amarnat, K.; Valentine, W.M.; Wetterau, L.A.; Graham, D.G. J. Org. Chem.1991, 56, 6924–6931; (d) Cheng, L.; Lightner, D.A. Synthesis1999, 1, 46–55; (e) Jones, R.A. Pyrroles, Part II; Wiley: New York, 1992; (f) Gribble, G.W. In Comprehensive Heterocyclic Chemistry II: Katrizky, A.R., Rees, C.W., Scriven, E.F., Eds.; Pergamon Press: Oxford, 1996; Vol. 2, p 207; (g) Minetto, G.; Raveglia, L.F.; Sega, A.; Taddei, M. Eur. J. Org. Chem.2005, 24, 5277–5288; (h) Chen, J.; Wu, H.; Zheng, Z.; Jin, C.; Zhang, X.; Su, W. Tetrahedron Lett.2006, 47, 5383–5387.
  • Dou, G.; Shi, C.; Shi, D.J. Comb. Chem.2008, 10, 810–813.
  • Wang, J.-Y.; Wang, X.-P.; Yu, Z.-S.; Yu, W.Adv. Synth. Catal.2009, 351, 2063–2066.
  • Li, Q.; Fan, A.; Lu, Z.; Cui, Y.; Lin, W.; Jia, Y.Org. Lett.2010, 12, 4066–4069.
  • Yan, R.-L.; Luo, J.; Wang, C.-X.; Ma, C.-W.; Huang, G.-S.; Liang, Y.-M.J. Org. Chem.2010, 75, 5395–5397.
  • Ngwerume, S.; Camp, J.E.J. Org. Chem.2010, 75, 6271–6274.
  • (a) Abbasinejad, M.A.; Khadije, C.; Hossein, A.A. Synlett2009, 2009 (7), 1115–1117 (b) Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D. Tet. Lett.2011, 52, 3937–3941
  • Maiti, S.; Biswas, S.; Jana, U.J. Org. Chem.2010, 75, 1674–1683.
  • Wang, Y.; Bi, X.; Li, D.; Liao, P.; Wang, Y.; Yang, J.; Zhang, Q.; Liu, Q.Chem. Commun.2011, 47, 809–811.
  • Bandyopadhyay, D.; Mukherjee, S.; Granados, J.C.; Short, J.D.; Banik, B.K.Eur. J. Med. Chem.2012, 50, 209–215.
  • Jiang, Y.; Chan, W.C.; Park, C.-M.J. Am. Chem. Soc.2012, 134, 4104–4107.
  • Anaraki-Ardakani, H.; Noei, M.; Karbalaeiharofteh, M.; Zomorodbaksh, S.E-J. Chem.2012, 9 (4), 2239–2244.
  • (a) Singh, J.; Verma, P.K.; Tiwari, K.; Singh, S.B. J. Korean Chem. Soc.2011, 55 (2), 153–156; (b) Tiwari, K.; Verma, P.K.; Singh, S.B.; Singh, J. Synth. Commun.2012, 42, 3021—3030; (c) Singh, S.B.; Tiwari, K.; Verma, P.K.; Srivastava, M.; Singh, J.; Tiwari, K.P. Supramol. Chem.2013, 25 (5), 255–262.
  • Villalonga, R.; Cao, R.; Fragoso, A.Chem. Rev.2007, 107, 3088–3116.
  • Szejtli, J.Chem. Rev.1998, 98, 1743–1753.
  • Hapiot, F.; Tilloy, S.; Monflier, E.Chem. Rev.2005, 106, 767–780.
  • Murthy, S.N.; Madhav, B.; Kumar, A.V.Tetrahedron2009, 65, 5251–5256.

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:

Order Reprints Request Corporate Permissions

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:

Request Academic Permissions

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.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.