European Journal of Chemistry

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

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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.


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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.

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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.
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