Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Ultrasonic Preparation and Reactivity of 4,5-dihydro-1H-pyrazole Derivatives

Author(s): Ahlem Guesmi and Naoufel Ben Hamadi*

Volume 19, Issue 6, 2022

Published on: 08 January, 2021

Page: [429 - 433] Pages: 5

DOI: 10.2174/1570178617666210108113916

Price: $65

Abstract

The regiospecific synthesis of 1H-pyrazole derivatives has been accomplished through the 1,3-dipolar cycloaddition of aryldiazoalkane to but-3-en-2-one. A convenient and inexpensive ultrasound- assisted preparation of cyclopropenes in good yields has been realized. The effect of solvent, ultrasonic power, frequency, reaction time and temperature of cyclopropenation were studied and the order of yield indicates ultrasound, 25 KHz > Ultrasound, 40 KHz > conventional synthesis method.

Keywords: 1, 3-Dipolar cycloaddition, ultrasound, frequency, Power, 4, 5-dihydro-1H-pyrazole, cyclopropenes.

Next »
Graphical Abstract
[1]
Hajlaoui, K.; Guesmi, A.; Ben Hamadi, N.; Msaddek, M. J. Heterocycl. Chem., 2018, 55, 2069-2074.
[http://dx.doi.org/10.1002/jhet.3246]
[2]
Bhuvaneswari, S.; Umadevi, M.; Vanajothi, R. Bioorg. Med. Chem. Lett., 2020, 30(21), 127593.
[http://dx.doi.org/10.1016/j.bmcl.2020.127593] [PMID: 33010447]
[3]
Adnan, C.; Adem, K. Opt. Mater., 2018, 85, 79-85.
[http://dx.doi.org/10.1016/j.optmat.2018.08.045]
[4]
Yangyang, Z. Bioorg. Med. Chem. Lett., 2020, 30127535.
[5]
Bansal, K.K.; Bhardwaj, J.K.; Saraf, P.; Thakur, V.K.; Sharma, P.C. Mater. Today Chem., 2020, 17100335.
[http://dx.doi.org/10.1016/j.mtchem.2020.100335]
[6]
Jayashri, D.B.; Rajendra, D.P.; Hemant, P.N. Bioorg. Med. Chem. Lett., 2020, 30127558.
[http://dx.doi.org/10.1016/j.bmcl.2020.127558] [PMID: 32961321]
[7]
Naimish, K.V.; Dhananjoy, M.; Smritilekha, B. Curr. Org. Chem., 2019, 23, 2505-2572.
[8]
Ben Hamadi, N.; Moncef, M. Tetrahedron Asymmetry, 2012, 23, 1689-1693.
[http://dx.doi.org/10.1016/j.tetasy.2012.11.005]
[9]
Ravasco, J.M.J.M.; Monteiro, C.M. Org. Chem. Front., 2017, 4, 1167-1198.
[http://dx.doi.org/10.1039/C7QO00054E]
[10]
Juma’a, R.D.; Mark, S.B.; Michael, J.S.; Susan, N.; Gordon, R.P. Tetrahedron, 1996, 52, 12509-12520.
[http://dx.doi.org/10.1016/0040-4020(96)00730-2]
[11]
Sankuviruthiyil, M.U.; Rohit, K.R.; Sankaran, R.; Gopinathan, A. Curr. Org. Chem., 2019, 23, 3137-3153.
[12]
Gogate, P.R. Chem. Eng. Prog., 2008, 47, 515-527.
[http://dx.doi.org/10.1016/j.cep.2007.09.014]
[13]
Hu, Y.; Zou, Y.; Wu, H.; Shi, D. Ultrason. Sonochem., 2012, 19(2), 264-269.
[http://dx.doi.org/10.1016/j.ultsonch.2011.07.006] [PMID: 21855389]
[14]
Clésia, C.N.; Mauro, K.; Clarivaldo, S.S.; Marco, A.Z.A. J. Braz. Chem. Soc., 2001, 12, 57-63.
[http://dx.doi.org/10.1590/S0103-50532001000100008]
[15]
Meiyu, G.; Johannes, F.; Tianyi, T.; Arseniy, V.P.; Vladimir, V.P.; Sergey, I.T.; Evgeniy, V.S.; Gleb, B.S. Nanoscale, 2017, 9, 7063-7070.
[http://dx.doi.org/10.1039/C7NR01841J] [PMID: 28513733]
[16]
Sven, R.; Tieyan, S.; Meiyu, G.; Mengmeng, S.; Johannes, F.Q.H. J. Colloid Interface Sci., 2019, 541, 407-417.
[http://dx.doi.org/10.1016/j.jcis.2019.01.103] [PMID: 30710823]
[17]
Margulis, M.A. High Energy Chem., 2004, 38, 135-142.
[http://dx.doi.org/10.1023/B:HIEC.0000027648.69725.98]
[18]
Guesmi, A.; Ladhari, N.; Sakli, F. Ultrason. Sonochem., 2013, 20(1), 571-579.
[http://dx.doi.org/10.1016/j.ultsonch.2012.04.012] [PMID: 22677454]
[19]
Ben Hamadi, N.; Msaddek, M. C. R. Chim., 2012, 15, 409-413.
[http://dx.doi.org/10.1016/j.crci.2012.02.004]
[20]
Albert, L.; Artur, M.S.S.; Diana, C.G.A.P.; José, A.S.C.; Ibon, A.; José, E.; József, J. Eur. J. Org. Chem., 2004, 4672-4679.
[21]
Caramella, P.; Gandour, R.W.; Hall, J.A.; Deville, C.G.; Houk, K.N. J. Am. Chem. Soc., 1977, 99, 385-392.
[http://dx.doi.org/10.1021/ja00444a013]
[22]
Saurabh, P.; Balbir, K.; Anupama, P.; Harish, K. Curr. Org. Chem., 2013, 17, 1790-1828.
[http://dx.doi.org/10.2174/13852728113179990018]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy