European Journal of Chemistry

Reactions under increased pressure: The reactivity of functionally substituted 3-oxo-2-arylhydrazones toward active methylene reagents in Q-tube

Crossmark


Main Article Content

Douaa Salman AlMarzouq

Abstract

A one-pot two-component reaction of 3-oxo-2-arylhydrazones with active methylene nitriles under high pressure in a Q-tube safe reactor was reported. Comparison between conventional and Q-tube safe reactor-assisted synthesis of organic compounds was done by comparing total reaction time and percentage yield. The results show that the compound 5-cyano-6-oxo-1,4-diphenyl-1,6-dihydro-pyridazine-3-carboxylic acid ethyl ester (3) was synthesized within 2 h in a yield of 97%. In addition, the pyrazolo[3,4-c]pyridines 5b and 5c were obtained in yields of 93 and 95% within 1 h reaction time, respectively. The obtained results suggest that Q-tube safe reactor-assisted syntheses were led to higher product yields within very short reaction times.


icon graph This Abstract was viewed 857 times | icon graph Article PDF downloaded 501 times

How to Cite
(1)
AlMarzouq, D. S. Reactions under Increased Pressure: The Reactivity of Functionally Substituted 3-Oxo-2-Arylhydrazones Toward Active Methylene Reagents in Q-Tube. Eur. J. Chem. 2021, 12, 154-158.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Abdelhamid, I.; Elnagdi, M.; Nasra, M. Synlett. 2009, (20), 3237-3251.
https://doi.org/10.1055/s-0029-1218518

[2]. Konkoy, C. S.; Fick, D. B.; Cai, S. X.; Lan, N. C.; Keana, J. F. U.S. Patent No. 6,680,332. Washington, DC: U.S. Patent and Trademark Office, 2004.

[3]. Zhang, Z.; Yan, J.; Leung, D.; Costello, P. C.; Sanghera, J. U.S. Patent No. 6,214,813. Washington, DC: U.S. Patent and Trademark Office, 2001.

[4]. Elnagdi, M. H.; Sadek, K. U.; Moustafa, M. S. Adv. Heterocyclic Chem. 2013, 109, 241-312.
https://doi.org/10.1016/B978-0-12-407777-5.00003-8

[5]. Elnagdi, M. H.; Moustafa, M. S.; Al-Mousawi, S. M.; Mekheimer, R. A.; Sadek, K. U. Mol. Divers. 2015, 19 (3), 625-651.
https://doi.org/10.1007/s11030-015-9594-2

[6]. Mekheimer, R.; Shaker, R. M.; Sadek, K. U.; Otto, H. H. Heterocycl. Comm. 1997, 3 (3), 217-222.
https://doi.org/10.1515/HC.1997.3.3.217

[7]. Horikoshi, S.; Osawa, A.; Sakamoto, S.; Serpone, N. Appl. Catal. A Gen. 2013, 460-461, 52-60.
https://doi.org/10.1016/j.apcata.2013.04.022

[8]. Kappe, C. O.; Stadler, A.; Dallingea, D.; Mannhold, R. Microwaves in Organic and Medicinal Chemistry, Sec. ed. 52.; Wiley-VCH, 2012.

[9]. Kiselev, V. D.; Kornilov, D. A.; Lekomtseva, I. I.; Konovalov, A. I. Int. J. Chem. Kinet. 2015, 47 (5), 289-301.
https://doi.org/10.1002/kin.20908

[10]. Alzaydi, K. M.; Abojabal, N. S.; Elnagdi, M. H. Tetrahedron Lett. 2016, 57 (32), 3596-3599.
https://doi.org/10.1016/j.tetlet.2016.05.035

[11]. Moustafa, M. S.; Al-Mousawi, S. M.; Elnagdi, M. H. RSC Adv. 2016, 6 (93), 90840-90845.
https://doi.org/10.1039/C6RA19535K

[12]. AlMarzouq, D. S.; Zaky, O. S.; AlNajjar, A. A.; Sadek, K. U. Eur. J. Chem. 2016, 7 (3), 347-351.
https://doi.org/10.5155/eurjchem.7.3.347-351.1473

[13]. Makhseed, S.; Hassaneen, H. M. E.; Elnagdi, M. H. Z. Naturforsch. B J. Chem. Sci. 2007, 62 (4), 529-536.
https://doi.org/10.1515/znb-2007-0407

[14]. Behbehani, H.; Ibrahim, H. M. A. Tetrahedron 2013, 69 (49), 10535-10543.
https://doi.org/10.1016/j.tet.2013.10.061

Supporting Agencies

Kuwait University Research Administration-RSP unit general facilities of the Faculty of Science, GFS GS 02/01, GS 03/01, GS 01/05), Kuwait.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).