Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Solvent-free, Silica Catalyzed Intriguing Conversion of 3- Hydrazonobutan-2-one Oxime into Biacetyl Bis-hydrazone Schiff Bases

Author(s): Ranjana Aggarwal*, Mona Hooda, Prince Kumar and Garima Sumran

Volume 18, Issue 7, 2021

Published on: 18 August, 2020

Page: [532 - 537] Pages: 6

DOI: 10.2174/1570178617999200818210859

Price: $65

Abstract

An expeditious and operationally simple reaction between 3-hydrazonobutan-2-one oxime and different substituted benzaldehydes in the presence of silica afforded an unexpected product, biacetyl bis-hydrazone Schiff bases in good yield on grinding in a mortar at room temperature, instead of expected product 3-(aryl)methylenehydrazonobutan-2-one oxime. Mild reaction conditions involving recyclable mineral support silica, environmentally benign and good yield in short reaction time are remarkable advantages of this protocol. Products were characterized by IR, NMR (1H and 13C) and elemental analyses.

Keywords: 3-Hydrazonobutan-2-one oxime, biacetyl bis-hydrazone Schiff bases, 3-(aryl)methylenehydrazonobutan-2-one oxime, azine, solvent-free synthesis, silica gel.

« Previous Next »
Graphical Abstract

[1]
Schiff, H. Ann. Chem. Suppl., 1864, 3, 343-349.
[2]
Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Molecules, 2013, 18(10), 12264-12289.
[http://dx.doi.org/10.3390/molecules181012264] [PMID: 24108395]
[3]
Zhong, X.; Yi, J.; Sun, J.; Wei, H-L.; Liu, W-S.; Yu, K-B. Eur. J. Med. Chem., 2006, 41(9), 1090-1092.
[http://dx.doi.org/10.1016/j.ejmech.2006.05.009] [PMID: 16782235]
[4]
Elmizadeh, H.; Soleimani, M.; Faridbod, F.; Bardajee, G.R. Colloid Polym. Sci., 2018, 296, 1581-1590.
[http://dx.doi.org/10.1007/s00396-018-4375-y]
[5]
Ganjali, M.R.; Norouzi, P.; Daftari, A.; Faridbod, F.; Salavati-Niasari, M. Sens. Actuators B Chem., 2007, 120, 673-678.
[http://dx.doi.org/10.1016/j.snb.2006.03.028]
[6]
Ganjali, M.R.; Matloobi, P.; Ghorbani, M.; Norouzi, P.; Salavati-Niasari, M. Bull. Korean Chem. Soc., 2005, 26, 38-42.
[http://dx.doi.org/10.5012/bkcs.2005.26.1.038]
[7]
Malik, M.A.; Dar, O.A.; Gull, P.; Wani, M.Y.; Hashmi, A.A. MedChemComm, 2017, 9(3), 409-436.
[http://dx.doi.org/10.1039/C7MD00526A] [PMID: 30108933]
[8]
Mahmoudi, G.; Zaręba, J.K.; Gurbanov, A.V.; Bauzá, A.; Zubkov, F.I.; Kubicki, M.; Stilinović, V.; Kinzhybalo, V.; Frontera, A. Eur. J. Inorg. Chem., 2017, 4763-4772.
[http://dx.doi.org/10.1002/ejic.201700955]
[9]
Ardakani, M.M.; Sadeghi, A.; Salavati-Niasari, M. Talanta, 2005, 66(4), 837-843.
[http://dx.doi.org/10.1016/j.talanta.2004.12.039] [PMID: 18970061]
[10]
Tanaka, K.; Toda, F. Chem. Rev., 2000, 100(3), 1025-1074.
[http://dx.doi.org/10.1021/cr940089p] [PMID: 11749257]
[11]
Sumran, G.; Aggarwal, R.; Hooda, M.; Sanz, D.; Claramunt, R.M. Synth. Commun., 2018, 48, 439-446.
[http://dx.doi.org/10.1080/00397911.2017.1407791]]
[12]
Aggarwal, R.; Kumar, S.; Singh, S.P. J. Sulfur Chem., 2012, 33, 521-525.
[http://dx.doi.org/10.1080/17415993.2012.711331]
[13]
Aggarwal, R. Mamta, Sumran, G. Arkivoc 2019, vi, 190-199.
[14]
Aggarwal, R.; Sumran, G.; Garg, N.; Aggarwal, A. Eur. J. Med. Chem., 2011, 46(7), 3038-3046.
[http://dx.doi.org/10.1016/j.ejmech.2011.04.041] [PMID: 21558044]
[15]
Aggarwal, R.; Rani, C.; Sumran, G. Synth. Commun., 2014, 44, 923-928.
[http://dx.doi.org/10.1080/00397911.2013.832775]
[16]
Sumran, G.; Aggarwal, R. J. Sulfur Chem., 2015, 36, 170-177.
[http://dx.doi.org/10.1080/17415993.2014.996221]
[17]
Mamta, Aggarwal. R.; Sadana, R.; Ilag, J.; Sumran, G. Bioorg. Chem., 2019, 86, 288-295.
[http://dx.doi.org/10.1016/j.bioorg.2019.01.049] [PMID: 30735849]
[18]
Sumran, G.; Aggarwal, R.; Mittal, A.; Aggarwal, A.; Gupta, A. Bioorg. Chem., 2019, 88, 102932.
[http://dx.doi.org/10.1016/j.bioorg.2019.102932] [PMID: 31028990]
[19]
Balalaie, S.; Arabanian, A. Green Chem., 2000, 2, 274-276.
[http://dx.doi.org/10.1039/b006201o]
[20]
Onitsuka, S.; Jin, Y.Z.; Shaikh, A.C.; Furuno, H.; Inanaga, J. Molecules, 2012, 17(10), 11469-11483.
[http://dx.doi.org/10.3390/molecules171011469] [PMID: 23018922]
[21]
Banerjee, A.K.; Mimo’, M.S.L.; Vegas, W.J.V. Russ. Chem. Rev., 2001, 70, 971-990.
[http://dx.doi.org/10.1070/RC2001v070n11ABEH000642]
[22]
Bolger, J.A.; Ferguson, G.; James, J.P.; Long, C.; McArdle, P.; Vos, J.G. J. Chem. Soc., Dalton Trans., 1993, 1577-1583.
[http://dx.doi.org/10.1039/dt9930001577]
[23]
Yang, S-M.; Xu, Y-T.; Zhang, B-H. Acta Crystallogr., 2010, E66, o1174.
[24]
Abkenar, S.D.; Dahaghin, Z.; Sadeghi, H.B.; Hosseini, M.; Salavati-Niasari, M. J. Anal. Chem., 2011, 66, 612-617.
[http://dx.doi.org/10.1134/S1061934811060062]
[25]
Mukherjee, A.; Chakrabarty, R.; Ng, S.W.; Patra, G.K. Inorg. Chim. Acta, 2010, 363, 1707-1712.
[http://dx.doi.org/10.1016/j.ica.2009.12.009]
[26]
Horst, H.; Joerg, M.; Detlef, R. Verfahren Zur Silberfreien Bildaufzeichnung. Ger. (East)., Patent DD157124A1, 1982.

Rights & Permissions Print Cite
Article Metrics
17
1
© 2024 Bentham Science Publishers | Privacy Policy