Ionic Liquid Catalyzed One-Pot, Three Component Synthesis of Dihydropyrano[2,3-c]pyrazole under Green Conditions

S. Yakaiah; G. Buchappa; K. Durgaprasad; K. Ravibabu; P. Aparna

doi:10.14233/ajchem.2016.20008

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Issue Published : August 10, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ionic Liquid Catalyzed One-Pot, Three Component Synthesis of Dihydropyrano[2,3-c]pyrazole under Green Conditions

https://doi.org/10.14233/ajchem.2016.20008

S. Yakaiah

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

G. Buchappa

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

K. Durgaprasad

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

K. Ravibabu

Natco Research Centre, B-13, Industrial Estate, Sanathnagar, Hyderabad-500 018, India

P. Aparna

Jawaharlal Nehru Technological University, Hyderabad-500 085, India

Corresponding Author(s) : S. Yakaiah

prasannasargam1984@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 11 (2016): Vol 28 Issue 11
Article Published : August 11, 2016

Abstract

A new series of 6-amino-3-methyl-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile derivatives were synthesized, where the three-component reaction of ethyl 3-oxobutanoate, hydrazinehydrate, aromatic aldehyde and malononitrile performed under green conditions by using ionic liquid [Bmim]BF₄ as reaction media. This method has the several advantages such as good yields, shorter reaction time, operational simplicities and eco-friendliness. The chemical structures of all the synthesized compounds were well characterized by physical, analytical and spectroscopic techniques.

Keywords

Multi-component reaction Ionic liquid Dihydropyrano[2,3-c]pyrazole

Yakaiah, S., Buchappa, G., Durgaprasad, K., Ravibabu, K., & Aparna, P. (2016). Ionic Liquid Catalyzed One-Pot, Three Component Synthesis of Dihydropyrano[2,3-c]pyrazole under Green Conditions. Asian Journal of Chemistry, 28(11), 2441–2445. https://doi.org/10.14233/ajchem.2016.20008

Download Citation

References

L.D.S. Yadav, S. Singh and V.K. Rai, Tetrahedron Lett., 50, 2208 (2009); doi:10.1016/j.tetlet.2009.02.166.
M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol and P. Machado, Chem. Rev., 109, 4140 (2009); doi:10.1021/cr9001098.
M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta and H.G. Bonacorso, Chem. Rev., 108, 2015 (2008); doi:10.1021/cr078399y.
H. Olivier-Bourbigou, L. Magna and D. Morvan, Appl. Catal. A, 373, 1 (2010); doi:10.1016/j.apcata.2009.10.008.
L. Suresh, Y. Poornachandra, S. Kanakaraju, C. Ganesh Kumar and G.V.P. Chandramouli, Org. Biomol. Chem., 13, 7294 (2015); doi:10.1039/C5OB00693G.
P.S. Vijay Kumar, L. Suresh and G.V.P. Chandramouli, J. Saudi Chem. Soc.;. doi:10.1016/j.jscs.2015.08.001.
N. Isambert, M.M.S. Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez and T. Constantieux, Chem. Soc. Rev., 40, 1347 (2011); doi:10.1039/C0CS00013B.
A.M. Zonouz, I. Eskandari and H.R. Khavasi, Tetrahedron Lett., 535, 519 (2012); doi:10.1016/j.tetlet.2012.08.010.
S. Horikoshi, T. Hamamura, M. Kajitani, M. Yoshizawa-Fujita and N. Serpone, Org. Process Res. Dev., 12, 1089 (2008); doi:10.1021/op800135t.
N.D. Vala, H.H. Jardosh and M.P. Patel, Chin. Chem. Lett., 5, 2 (2015); doi:10.1016/j.cclet.2015.09.020.
T.A. Farghaly, N.A. Abdel Hafez, E.A. Ragab, H.M. Awad and M.M. Abdalla, Eur. J. Med. Chem., 45, 492 (2010); doi:10.1016/j.ejmech.2009.10.033.
H. Kumar, D. Saini, S. Jain and N. Jain, Eur. J. Med. Chem., 70, 248 (2013); doi:10.1016/j.ejmech.2013.10.004.
J. Cai, M. Baugh, D. Black, C. Long, D. Jonathan Bennett, M. Dempster, X. Fradera, J. Gillespie, F. Andrews, S. Boucharens, J. Bruin, K.S. Cameron, I. Cumming, W. Hamilton, P.S. Jones, A. Kaptein, E. Kinghorn, M. Maidment, I. Martin, A. Mitchell, Z. Rankovic, J. Robinson, P. Scullion, J.C.M. Uitdehaag, P. Vink, P. Westwood, M. van Zeeland, L. van Berkom, M. Bastiani and T. Meulemans, Bioorg. Med. Chem. Lett., 20, 4350 (2010); doi:10.1016/j.bmcl.2010.06.072.
O.L. Kobzar, V.V. Trush, V.Y. Tanchuk, I.I. Voronov, A.S. Peregudov, P.A. Troshin and A.I. Vovk, Mendeleev Commun., 25, 199 (2015); doi:10.1016/j.mencom.2015.05.013.
M.C. Witschel, M. Rottmann, A. Schwab, U. Leartsakulpanich, P. Chitnumsub, M. Seet, S. Tonazzi, G. Schwertz, F. Stelzer, T. Mietzner, C. McNamara, F. Thater, C. Freymond, A. Jaruwat, C. Pinthong, P. Riangrungroj, M. Oufir, M. Hamburger, P. Mäser, L.M. Sanz-Alonso, S. Charman, S. Wittlin, Y. Yuthavong, P. Chaiyen and F. Diederich, J. Med. Chem., 58, 3117 (2015); doi:10.1021/jm501987h.
S. Ambethkar, V. Padmini and N. Bhuvanesh, J. Adv. Res., 6, 975 (2014); doi:10.1016/j.jare.2014.11.011.
P.P. Bora, M. Bihani and G. Bez, J. Mol. Catal. B, 92, 24 (2013); doi:10.1016/j.molcatb.2013.03.015.
M. Bihani, P.P. Bora, G. Bez and H. Askari, ACS Sustain. Chem. Eng., 1, 440 (2013); doi:10.1021/sc300173z.
J.B. Gujar, M.A. Chaudhari, D.S. Kawade and M.S. Shingare, Tetrahedron Lett., 55, 6030 (2014); doi:10.1016/j.tetlet.2014.08.127.
F. Tamaddon and M. Alizadeh, Tetrahedron Lett., 55, 3588 (2014); doi:10.1016/j.tetlet.2014.04.122.

References

L.D.S. Yadav, S. Singh and V.K. Rai, Tetrahedron Lett., 50, 2208 (2009); doi:10.1016/j.tetlet.2009.02.166.

M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol and P. Machado, Chem. Rev., 109, 4140 (2009); doi:10.1021/cr9001098.

M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta and H.G. Bonacorso, Chem. Rev., 108, 2015 (2008); doi:10.1021/cr078399y.

H. Olivier-Bourbigou, L. Magna and D. Morvan, Appl. Catal. A, 373, 1 (2010); doi:10.1016/j.apcata.2009.10.008.

L. Suresh, Y. Poornachandra, S. Kanakaraju, C. Ganesh Kumar and G.V.P. Chandramouli, Org. Biomol. Chem., 13, 7294 (2015); doi:10.1039/C5OB00693G.

P.S. Vijay Kumar, L. Suresh and G.V.P. Chandramouli, J. Saudi Chem. Soc.;. doi:10.1016/j.jscs.2015.08.001.

N. Isambert, M.M.S. Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez and T. Constantieux, Chem. Soc. Rev., 40, 1347 (2011); doi:10.1039/C0CS00013B.

A.M. Zonouz, I. Eskandari and H.R. Khavasi, Tetrahedron Lett., 535, 519 (2012); doi:10.1016/j.tetlet.2012.08.010.

S. Horikoshi, T. Hamamura, M. Kajitani, M. Yoshizawa-Fujita and N. Serpone, Org. Process Res. Dev., 12, 1089 (2008); doi:10.1021/op800135t.

N.D. Vala, H.H. Jardosh and M.P. Patel, Chin. Chem. Lett., 5, 2 (2015); doi:10.1016/j.cclet.2015.09.020.

T.A. Farghaly, N.A. Abdel Hafez, E.A. Ragab, H.M. Awad and M.M. Abdalla, Eur. J. Med. Chem., 45, 492 (2010); doi:10.1016/j.ejmech.2009.10.033.

H. Kumar, D. Saini, S. Jain and N. Jain, Eur. J. Med. Chem., 70, 248 (2013); doi:10.1016/j.ejmech.2013.10.004.

J. Cai, M. Baugh, D. Black, C. Long, D. Jonathan Bennett, M. Dempster, X. Fradera, J. Gillespie, F. Andrews, S. Boucharens, J. Bruin, K.S. Cameron, I. Cumming, W. Hamilton, P.S. Jones, A. Kaptein, E. Kinghorn, M. Maidment, I. Martin, A. Mitchell, Z. Rankovic, J. Robinson, P. Scullion, J.C.M. Uitdehaag, P. Vink, P. Westwood, M. van Zeeland, L. van Berkom, M. Bastiani and T. Meulemans, Bioorg. Med. Chem. Lett., 20, 4350 (2010); doi:10.1016/j.bmcl.2010.06.072.

O.L. Kobzar, V.V. Trush, V.Y. Tanchuk, I.I. Voronov, A.S. Peregudov, P.A. Troshin and A.I. Vovk, Mendeleev Commun., 25, 199 (2015); doi:10.1016/j.mencom.2015.05.013.

M.C. Witschel, M. Rottmann, A. Schwab, U. Leartsakulpanich, P. Chitnumsub, M. Seet, S. Tonazzi, G. Schwertz, F. Stelzer, T. Mietzner, C. McNamara, F. Thater, C. Freymond, A. Jaruwat, C. Pinthong, P. Riangrungroj, M. Oufir, M. Hamburger, P. Mäser, L.M. Sanz-Alonso, S. Charman, S. Wittlin, Y. Yuthavong, P. Chaiyen and F. Diederich, J. Med. Chem., 58, 3117 (2015); doi:10.1021/jm501987h.

S. Ambethkar, V. Padmini and N. Bhuvanesh, J. Adv. Res., 6, 975 (2014); doi:10.1016/j.jare.2014.11.011.

P.P. Bora, M. Bihani and G. Bez, J. Mol. Catal. B, 92, 24 (2013); doi:10.1016/j.molcatb.2013.03.015.

M. Bihani, P.P. Bora, G. Bez and H. Askari, ACS Sustain. Chem. Eng., 1, 440 (2013); doi:10.1021/sc300173z.

J.B. Gujar, M.A. Chaudhari, D.S. Kawade and M.S. Shingare, Tetrahedron Lett., 55, 6030 (2014); doi:10.1016/j.tetlet.2014.08.127.

F. Tamaddon and M. Alizadeh, Tetrahedron Lett., 55, 3588 (2014); doi:10.1016/j.tetlet.2014.04.122.

Issue

Vol. 28 No. 11 (2016): Vol 28 Issue 11

Ionic Liquid Catalyzed One-Pot, Three Component Synthesis of Dihydropyrano[2,3-c]pyrazole under Green Conditions

Corresponding Author(s) : S. Yakaiah

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents