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A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media

Year 2011, Volume: 24 Issue: 2, 227 - 231, 05.04.2011

Abstract

A high yielding and fast method for the synthesis of 1,4-Dihydropyrano[2,3-c] pyrazole via one-pot, three component reaction of an aromatic aldehyde, malonitrile and 3-methyl-1-phenyl-2-pyrazolin-5-one using p-toluene sulfonic acid as a catalyst  is described

 

Keywords: p-toluene sulfonic acid, 1,4-dihydropyrano[2,3-c]pyrazole, one-pot.

 

                                      

References

  • Witte, E.C., Neubert, P., Roesoh, A., ”2H-1- benzopyran-2-on derivatives, process for their preparation and medicines containing these compounds“, Ger. Offen. DE., 3427985 (1986), Chem. Abstr. 104, 224915f (1986).
  • Hyama, T., Saimoto, H., ”2H-CHROMENE DERIVATIVE“, Jpn. KoKai Tokkyo Koho, JP. 62181276 (1987), Chem. Abstr. 108, 37645 (1988).
  • Armetso, D., Horspool, W.M., Martin, N., Ramos, A., Seaone, C.,” Synthesis of cyclobutenes by the novel photochemical ring contraction of 4- substituted pyrans“, J. Org. Chem., 54: 3069–3072 (1989).
  • Martin, L.N., Quinteiro, M., Seoane, C., Soto, J.L.,” Synthesis of 4H-pyrans“, Liebigs. Ann. Chem., 1: 101-104 (1991).
  • Maco, J.L., Martin, N., Grau, A.M., Seoane, C., Albert, A., Cano, F. H., ”Development of methods for the synthesis of chiral, highly functionalized 2- amino-4-aryl-4H-pyrans“, Tetrahedron., 50: 3509- 3528 (1994).
  • Li, C.J., Chan, T.H.,”Organic Reactions in Aqueous Media“, Wiley: New York (1997).
  • Grieco, P.A.,”Organic Synthesis in Water“, Ed., Thomson Science, Glasgow, Scotland (1998).
  • Li, C.J., ”Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update“, Chem. Rev., 105: 3095–3166 (2005).
  • Breslow, R., ”Hydrophobic effects on simple organic reactions in water“, Acc. Chem. Res., 24: 159–164 (1991).
  • Breslow, R., ”Determining the Geometries of Transition States by Use of Antihydrophobic Additives in Water“, Acc. Chem. Res., 37:471–478 (2004).
  • Narasimhulu, M., Mahesh, K.C., Reddy, T.S., Rajesh, K., Venkateswarlu, Y., ”Lanthanum(III) nitrate hexahydrate or p-toluenesulfonic acid catalyzed quinazolinones under solvent-free conditions“, Tetrahedron Lett., 47: 4381-4383 (2006). 4(3H)
  • GU J Sci., 24(2):227-231 (2011)/ Majid M. HERAVI1, Najme JAVANMARDI1, Hossein A.OSKOOIE1, Bita BAGHERNEJAD1
  • Anuradha, V.; Srinivas, P. V.; Aparna, P.; Rao, J. M.,” p-Toluenesulfonic acid catalyzed regiospecific nitration Tetrahedron Lett., 47: 4933-4935 (2006). metal nitrates“,
  • Li, T.; Souma, Y.; Xu, Q., ”Carbonylation of formaldehyde catalyzed by p-toluenesulfonic acid“, Catal. Today., 111: 288-291 (2006).
  • Bamoharram, F.F., Heravi, M.,”Catalytic Method for Synthesis of Aspirin by a Green, Efficient and Recyclable Solid Acid Catalyst Temperature“, J. Chin.Chem. Soc., 54: 1017-1020 (2007). M.M., Roshani, (Preyssler’s Anion) at Room [15] Heravi, M.M., Bakhtiari, H.A.,”Communication: KHSO4 Supported onto Bentonite, A Versatile Reagent for Aromatization of Hantzsch 1,4-Dihydropyridines“, J. Chin. Chem. Soc., 54: 579-582 (2007). K., Oskooie,
  • Heravi, M.M., Oskooie, H. A., Baghernejad, B.,”Facile, Regioselective and Green Synthesis of Ortho-nitrophenoles Using NaNO2, KHSO4“, J. Chin.Chem. Soc., 54: 767-770 (2007).
  • Zhou, J.F., Tu, S.J., Gao, Y., Ji, M., ”One pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives under microwave irradiation“, J. Org. Chem., 21: 742-745 (2001).
Year 2011, Volume: 24 Issue: 2, 227 - 231, 05.04.2011

Abstract

References

  • Witte, E.C., Neubert, P., Roesoh, A., ”2H-1- benzopyran-2-on derivatives, process for their preparation and medicines containing these compounds“, Ger. Offen. DE., 3427985 (1986), Chem. Abstr. 104, 224915f (1986).
  • Hyama, T., Saimoto, H., ”2H-CHROMENE DERIVATIVE“, Jpn. KoKai Tokkyo Koho, JP. 62181276 (1987), Chem. Abstr. 108, 37645 (1988).
  • Armetso, D., Horspool, W.M., Martin, N., Ramos, A., Seaone, C.,” Synthesis of cyclobutenes by the novel photochemical ring contraction of 4- substituted pyrans“, J. Org. Chem., 54: 3069–3072 (1989).
  • Martin, L.N., Quinteiro, M., Seoane, C., Soto, J.L.,” Synthesis of 4H-pyrans“, Liebigs. Ann. Chem., 1: 101-104 (1991).
  • Maco, J.L., Martin, N., Grau, A.M., Seoane, C., Albert, A., Cano, F. H., ”Development of methods for the synthesis of chiral, highly functionalized 2- amino-4-aryl-4H-pyrans“, Tetrahedron., 50: 3509- 3528 (1994).
  • Li, C.J., Chan, T.H.,”Organic Reactions in Aqueous Media“, Wiley: New York (1997).
  • Grieco, P.A.,”Organic Synthesis in Water“, Ed., Thomson Science, Glasgow, Scotland (1998).
  • Li, C.J., ”Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update“, Chem. Rev., 105: 3095–3166 (2005).
  • Breslow, R., ”Hydrophobic effects on simple organic reactions in water“, Acc. Chem. Res., 24: 159–164 (1991).
  • Breslow, R., ”Determining the Geometries of Transition States by Use of Antihydrophobic Additives in Water“, Acc. Chem. Res., 37:471–478 (2004).
  • Narasimhulu, M., Mahesh, K.C., Reddy, T.S., Rajesh, K., Venkateswarlu, Y., ”Lanthanum(III) nitrate hexahydrate or p-toluenesulfonic acid catalyzed quinazolinones under solvent-free conditions“, Tetrahedron Lett., 47: 4381-4383 (2006). 4(3H)
  • GU J Sci., 24(2):227-231 (2011)/ Majid M. HERAVI1, Najme JAVANMARDI1, Hossein A.OSKOOIE1, Bita BAGHERNEJAD1
  • Anuradha, V.; Srinivas, P. V.; Aparna, P.; Rao, J. M.,” p-Toluenesulfonic acid catalyzed regiospecific nitration Tetrahedron Lett., 47: 4933-4935 (2006). metal nitrates“,
  • Li, T.; Souma, Y.; Xu, Q., ”Carbonylation of formaldehyde catalyzed by p-toluenesulfonic acid“, Catal. Today., 111: 288-291 (2006).
  • Bamoharram, F.F., Heravi, M.,”Catalytic Method for Synthesis of Aspirin by a Green, Efficient and Recyclable Solid Acid Catalyst Temperature“, J. Chin.Chem. Soc., 54: 1017-1020 (2007). M.M., Roshani, (Preyssler’s Anion) at Room [15] Heravi, M.M., Bakhtiari, H.A.,”Communication: KHSO4 Supported onto Bentonite, A Versatile Reagent for Aromatization of Hantzsch 1,4-Dihydropyridines“, J. Chin. Chem. Soc., 54: 579-582 (2007). K., Oskooie,
  • Heravi, M.M., Oskooie, H. A., Baghernejad, B.,”Facile, Regioselective and Green Synthesis of Ortho-nitrophenoles Using NaNO2, KHSO4“, J. Chin.Chem. Soc., 54: 767-770 (2007).
  • Zhou, J.F., Tu, S.J., Gao, Y., Ji, M., ”One pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives under microwave irradiation“, J. Org. Chem., 21: 742-745 (2001).
There are 17 citations in total.

Details

Primary Language English
Journal Section Chemistry
Authors

Majid Heravi This is me

Najme Javanmardi This is me

Hossein Oskooie This is me

Bita Baghernejad

Publication Date April 5, 2011
Published in Issue Year 2011 Volume: 24 Issue: 2

Cite

APA Heravi, M., Javanmardi, N., Oskooie, H., Baghernejad, B. (2011). A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. Gazi University Journal of Science, 24(2), 227-231.
AMA Heravi M, Javanmardi N, Oskooie H, Baghernejad B. A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. Gazi University Journal of Science. April 2011;24(2):227-231.
Chicago Heravi, Majid, Najme Javanmardi, Hossein Oskooie, and Bita Baghernejad. “A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media”. Gazi University Journal of Science 24, no. 2 (April 2011): 227-31.
EndNote Heravi M, Javanmardi N, Oskooie H, Baghernejad B (April 1, 2011) A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. Gazi University Journal of Science 24 2 227–231.
IEEE M. Heravi, N. Javanmardi, H. Oskooie, and B. Baghernejad, “A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media”, Gazi University Journal of Science, vol. 24, no. 2, pp. 227–231, 2011.
ISNAD Heravi, Majid et al. “A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media”. Gazi University Journal of Science 24/2 (April 2011), 227-231.
JAMA Heravi M, Javanmardi N, Oskooie H, Baghernejad B. A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. Gazi University Journal of Science. 2011;24:227–231.
MLA Heravi, Majid et al. “A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media”. Gazi University Journal of Science, vol. 24, no. 2, 2011, pp. 227-31.
Vancouver Heravi M, Javanmardi N, Oskooie H, Baghernejad B. A Facile One Pot Synthesis Of Pyrano[2,3-C]Pyrazole Derivatives Using P-Toluene Sulfonic Acid In Aqueous Media. Gazi University Journal of Science. 2011;24(2):227-31.