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Ultrasound Assisted Synthesis of 1,5-Diaryl and 1,3,5-Triaryl-2-pyrazolines by Using KOH/EtOH System with Cu(I) Catalyst
Corresponding Author(s) : Arvind S. Burungale
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
1,5-Diaryl-2-pyrazolines and 1,3,5-triaryl-2-pyrazolines were synthesized in alcoholic potassium hydroxide in high yields within 1-6 min under ultrasound irradiation at room temperature.
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- T.J. Mason and J.P. Lorimer, Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry. Wiley, New York (1988).
- A. Gaplovsky, M. Gaplovsky, S. Toma and J.L. Luche, J. Org. Chem., 65, 8444 (2000); https://doi.org/10.1021/jo000611+.
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- G. Cravotto and P. Cintas, Chem. Soc. Rev., 35, 180 (2006); https://doi.org/10.1039/B503848K.
- W. Richards and A. Loomis, J. Am. Chem. Soc., 49, 3086 (1927); https://doi.org/10.1021/ja01411a015.
- L.A. Sarandeses, A. Mouriño andJ.-L. Luche, J. Chem. Soc. Chem. Commun., 798 (1992); https://doi.org/10.1039/C39920000798.
- C. Dupuy, C. Petrier, L.A. Sarandeses and J.L. Luche, Synth. Commun., 21, 643 (1991); https://doi.org/10.1080/00397919108020831.
- V. Bejan, C. Moldoveanu and I.I. Mangalagiu, Ultrason. Sonochem., 16, 312 (2009); https://doi.org/10.1016/j.ultsonch.2008.10.012.
- A.R. Katritzky and A.F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon, Oxford, edn 2 (2002).
- Q. Lin, D. Meloni, Y. Pan, M. Xia, J. Rodgers, S. Shepard, M. Li, L. Galya, B. Metcalf, T.-Y. Yue, P. Liu and J. Zhou, Org. Lett., 11, 1999 (2009); https://doi.org/10.1021/ol900350k.
- S. Fustero, S. Monteagudo, M. Sánchez-Roselló, S. Flores, P. Barrio and C. del Pozo, Chem. Eur. J., 16, 9835 (2010); https://doi.org/10.1002/chem.201000615.
- S. Comesse, M. Sanselme and A. Daïch, J. Org. Chem., 73, 5566 (2008); https://doi.org/10.1021/jo702752w.
- K. Damera, K.L. Reddy and G.V.M. Sharma, Lett. Org. Chem., 6, 151 (2009); https://doi.org/10.2174/157017809787582834.
- A. Levai, ARKIVOC, 344 (2005); https://doi.org/10.3998/ark.5550190.0006.929.
- A.M. Fahmy, A.A. Hassa and R.A. Ahmed, Indian J. Chem., 26B, 884 (1987).
- R.A. Nugent, M. Murphy, S.T. Schlachter, C.J. Dunn, R.J. Smith, L.A. Staite, L.A. Galinet, S.K. Shields, D.G. Aspar, K.A. Richard and N.A. Rohloff, J. Med. Chem., 36, 134 (1993); https://doi.org/10.1021/jm00053a017.
- V. Rangari, V.N. Gupta and C.K. Atal, Indian J. Pharm. Sci., 52, 158 (1990).
- M.I. Husain and S. Shukla, Indian J. Chem., 25B, 983 (1986).
- S. Rich and J.G. Horsfall, Chem. Abstr., 46, 11543 (1952).
- H. Kawazura, Y. Takahashi, Y. Shiga, F. Shimada, N. Ohto and A. Tamura, Jpn. J. Pharmacol., 73, 317 (1997); https://doi.org/10.1254/jjp.73.317.
- Z.-P. Lin and J.-T. Li, E-J. Chem., 9, 267 (2012); https://doi.org/10.1155/2012/364798.
- R. Gupta, N. Gupta and A. Jain, Indian J. Chem., 49B, 351 (2010).
- M. Kidwai, S. Kukreja and R. Thakur, Lett. Org. Chem., 3, 135 (2006); https://doi.org/10.2174/157017806775224170.
- M.A.H. Zahran, H.F. Salama, Y.G. Abdin and A.M. Gamal-Eldeen, J. Chem. Sci., 122, 587 (2010); https://doi.org/10.1007/s12039-010-0093-9.
- A. Goyal, S. Sharma and J. Gaba, Indian J. Chem., 56B, 334 (2017).
- V. Malhotra, S. Pathak, R. Nath, D. Mukerjee and K. Shankar, Indian J. Chem., 41B, 1310 (2002).
- A. Tiwari, S. Fatma A. Bishnoi, A. Srivastava and B. Banerjee, Indian J. Chem., 56B, 317 (2017).
- R. Fazaeli, Open Catalysis J., 3, 79 (2010); https://doi.org/10.2174/1876214X01003010079.
- B. Holla and M. Mahalinga, Indian J. Chem., 45B, 568 (2002).
- S. Mokle, A. Vibhute S. Khansole, S. Zangade and Y. Vibhute, Res. J. Pharm. Biol. Chem. Sci., 1, 631 (2010).
- S. Sridhar and Y. Rajendraprasad, E-J. Chem., 9, 1810 (2012); https://doi.org/10.1155/2012/476989.
- S. Paul, K. Pradhan and A.R. Das, Green Chem., 3, 111 (2016); https://doi.org/10.2174/2213346103666151203203139.
- P. Bhat, G. Shridhar, S. Ladage and L. Ravishankar, J. Chem. Sci., 129, 1441 (2017); https://doi.org/10.1007/s12039-017-1327-x.
- N. Uzma, B. Khaja Mohinuddin Salar, B. Kumar, N. Aziz, M. David and V. Reddy, Int. J. Environ. Res. Public Health, 5, 139 (2008); https://doi.org/10.3390/ijerph5030139.
References
T.J. Mason and J.P. Lorimer, Sonochemistry: Theory, Application and Uses of Ultrasound in Chemistry. Wiley, New York (1988).
A. Gaplovsky, M. Gaplovsky, S. Toma and J.L. Luche, J. Org. Chem., 65, 8444 (2000); https://doi.org/10.1021/jo000611+.
R.R. Deshmukh, R. Rajagopal and K.V. Srinivasan, Chem. Commun., 17, 1544 (2001); https://doi.org/10.1039/b104532f.
G. Cravotto and P. Cintas, Chem. Soc. Rev., 35, 180 (2006); https://doi.org/10.1039/B503848K.
W. Richards and A. Loomis, J. Am. Chem. Soc., 49, 3086 (1927); https://doi.org/10.1021/ja01411a015.
L.A. Sarandeses, A. Mouriño andJ.-L. Luche, J. Chem. Soc. Chem. Commun., 798 (1992); https://doi.org/10.1039/C39920000798.
C. Dupuy, C. Petrier, L.A. Sarandeses and J.L. Luche, Synth. Commun., 21, 643 (1991); https://doi.org/10.1080/00397919108020831.
V. Bejan, C. Moldoveanu and I.I. Mangalagiu, Ultrason. Sonochem., 16, 312 (2009); https://doi.org/10.1016/j.ultsonch.2008.10.012.
A.R. Katritzky and A.F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon, Oxford, edn 2 (2002).
Q. Lin, D. Meloni, Y. Pan, M. Xia, J. Rodgers, S. Shepard, M. Li, L. Galya, B. Metcalf, T.-Y. Yue, P. Liu and J. Zhou, Org. Lett., 11, 1999 (2009); https://doi.org/10.1021/ol900350k.
S. Fustero, S. Monteagudo, M. Sánchez-Roselló, S. Flores, P. Barrio and C. del Pozo, Chem. Eur. J., 16, 9835 (2010); https://doi.org/10.1002/chem.201000615.
S. Comesse, M. Sanselme and A. Daïch, J. Org. Chem., 73, 5566 (2008); https://doi.org/10.1021/jo702752w.
K. Damera, K.L. Reddy and G.V.M. Sharma, Lett. Org. Chem., 6, 151 (2009); https://doi.org/10.2174/157017809787582834.
A. Levai, ARKIVOC, 344 (2005); https://doi.org/10.3998/ark.5550190.0006.929.
A.M. Fahmy, A.A. Hassa and R.A. Ahmed, Indian J. Chem., 26B, 884 (1987).
R.A. Nugent, M. Murphy, S.T. Schlachter, C.J. Dunn, R.J. Smith, L.A. Staite, L.A. Galinet, S.K. Shields, D.G. Aspar, K.A. Richard and N.A. Rohloff, J. Med. Chem., 36, 134 (1993); https://doi.org/10.1021/jm00053a017.
V. Rangari, V.N. Gupta and C.K. Atal, Indian J. Pharm. Sci., 52, 158 (1990).
M.I. Husain and S. Shukla, Indian J. Chem., 25B, 983 (1986).
S. Rich and J.G. Horsfall, Chem. Abstr., 46, 11543 (1952).
H. Kawazura, Y. Takahashi, Y. Shiga, F. Shimada, N. Ohto and A. Tamura, Jpn. J. Pharmacol., 73, 317 (1997); https://doi.org/10.1254/jjp.73.317.
Z.-P. Lin and J.-T. Li, E-J. Chem., 9, 267 (2012); https://doi.org/10.1155/2012/364798.
R. Gupta, N. Gupta and A. Jain, Indian J. Chem., 49B, 351 (2010).
M. Kidwai, S. Kukreja and R. Thakur, Lett. Org. Chem., 3, 135 (2006); https://doi.org/10.2174/157017806775224170.
M.A.H. Zahran, H.F. Salama, Y.G. Abdin and A.M. Gamal-Eldeen, J. Chem. Sci., 122, 587 (2010); https://doi.org/10.1007/s12039-010-0093-9.
A. Goyal, S. Sharma and J. Gaba, Indian J. Chem., 56B, 334 (2017).
V. Malhotra, S. Pathak, R. Nath, D. Mukerjee and K. Shankar, Indian J. Chem., 41B, 1310 (2002).
A. Tiwari, S. Fatma A. Bishnoi, A. Srivastava and B. Banerjee, Indian J. Chem., 56B, 317 (2017).
R. Fazaeli, Open Catalysis J., 3, 79 (2010); https://doi.org/10.2174/1876214X01003010079.
B. Holla and M. Mahalinga, Indian J. Chem., 45B, 568 (2002).
S. Mokle, A. Vibhute S. Khansole, S. Zangade and Y. Vibhute, Res. J. Pharm. Biol. Chem. Sci., 1, 631 (2010).
S. Sridhar and Y. Rajendraprasad, E-J. Chem., 9, 1810 (2012); https://doi.org/10.1155/2012/476989.
S. Paul, K. Pradhan and A.R. Das, Green Chem., 3, 111 (2016); https://doi.org/10.2174/2213346103666151203203139.
P. Bhat, G. Shridhar, S. Ladage and L. Ravishankar, J. Chem. Sci., 129, 1441 (2017); https://doi.org/10.1007/s12039-017-1327-x.
N. Uzma, B. Khaja Mohinuddin Salar, B. Kumar, N. Aziz, M. David and V. Reddy, Int. J. Environ. Res. Public Health, 5, 139 (2008); https://doi.org/10.3390/ijerph5030139.