

Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube
Kamal Usef Sadek (1,*)





(1) Chemistry Department, Faculty of Science, Minia University, 61519, Minia, Egypt
(2) Chemistry Department, Faculty of Science at Qena, South Valley University, 83512, Qena, Egypt
(3) Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, 13060, Safat, Kuwait
(4) Chemistry Department, Faculty of Science at Qena, South Valley University, 83512, Qena, Egypt
(5) Chemistry Department, Faculty of Science, Cairo University, 12613, Giza, Egypt
(*) Corresponding Author
Received: 11 Nov 2016 | Revised: 21 Nov 2016 | Accepted: 03 Dec 2016 | Published: 31 Dec 2016 | Issue Date: December 2016
Abstract
A novel multi-component reaction between arylhydrazonals, malononitrile and aromatic aldehydes under high pressure utilizing Q-tube was carried out. The reaction of arylhydrazonal (1j) with malononitrile and aromatic aldehydes afforded the corresponding biphenyl derivatives (4). However, compound 1h reacted with malononitrile and aromatic aldehydes (7) to afford pyridazino[5,4,3-de]1,6-naphthyridine-7-carbonitrile derivatives (8). In contrast, the arylhydrazonal (1k) at the same reaction conditions afforded the corresponding pyridazinoquinazoline derivative (22). A rationalization for the difference in behavior for reaction of compounds 1h-k with malononitrile and aromatic aldehydes was postulated. Based on these findings a mechanism to account for the formation of the reaction products is suggested excluding possible initial dimerization of malononitrile as has been previously reported.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.7.4.468-472.1508
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Funding information
Minia University, 61519, Minia, Egypt and College of Technological Studies, Public Authority for Applied Education and Training, 13060, Safat, Kuwait
Citations
[1]. Mohamed R. Eletmany, Marzough Aziz Albalawi, Reem A.K. Alharbi, Rokaia B. Elamary, Abd El-Fattah A. Harb, Moghraby A. Selim, Asmaa Sayed Abdelgeliel, Entesar A. Hassan, Islam M. Abdellah
Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies
Journal of Saudi Chemical Society 27(3), 101647, 2023
DOI: 10.1016/j.jscs.2023.101647

[2]. Fatma Ahmed Abo Elsoud, Mohamed Abd-Elmonem, Mohamed Abo Elsebaa, Kamal Usef Sadek
Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives
European Journal of Chemistry 10(2), 166, 2019
DOI: 10.5155/eurjchem.10.2.166-170.1851

[3]. Afaf Abdel Hamid, Mohamed Abd‐Elmonem, Alaa M. Hayallah, Fatma A. Abo Elsoud, Kamal U. Sadek
Glycerol: A Promising Benign Solvent for Catalyst Free One‐Pot Multi‐Component Synthesis of Pyrano[2,3‐c]pyrazoles and Tetrahydro‐benzo[b]pyrans at Ambient Temperature
ChemistrySelect 2(33), 10689, 2017
DOI: 10.1002/slct.201702011

[4]. Douaa Salman AlMarzouq, Noha M. Hilmy Elnagdi
Glycerol and Q-Tubes: Green Catalyst and Technique for Synthesis of Polyfunctionally Substituted Heteroaromatics and Anilines
Molecules 24(9), 1806, 2019
DOI: 10.3390/molecules24091806

[5]. Mallu Lavanya, Chong Lin, Jincheng Mao, Dhakshanamurthy Thirumalai, Sreenath Reddy Aabaka, Xiaojiang Yang, Jinhua Mao, Zhiyu Huang, Jinzhou Zhao
Synthesis and Anticancer Properties of Functionalized 1,6-Naphthyridines
Topics in Current Chemistry 379(2), , 2021
DOI: 10.1007/s41061-020-00314-6

[6]. Majdah AL-Johani, Khadijah Al-Zaydi, Sameera Mousally, Norah Alqahtani, Noha Elnagdi, Mohamed Elnagdi
Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes
Molecules 22(12), 2114, 2017
DOI: 10.3390/molecules22122114

References
[1]. Elnagdi, M. H.; Sadek, K. U.; Moustafa, M. S. Adv. Heterocycl. Chem. 2013, 103, 241-312.
https://doi.org/10.1016/B978-0-12-407777-5.00003-8
[2]. 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
[3]. Mekhaeimer, R. A.; Shaker, R. M.; Sadek, K. U.; Otto, H. H. Heterocycl. Commun. 1997, 3, 217-221.
[4]. Abd El Latif, F. M.; Barsy, M. A.; Aref, A. M.; Sadek, K. U. Green Chem. 2002, 4, 196-198.
https://doi.org/10.1039/b110723m
[5]. Al-Zaydi, K. M.; Borik, R. M.; Elnagdi, M. H. Molecules 2003, 8, 910-923.
https://doi.org/10.3390/81200910
[6]. Al-Saleh, B.; Hilmy, N. M.; El-Apasery, M. A.; Elnagdi, M. H. J. Heterocylic Chem. 2006, 43, 157-158.
https://doi.org/10.1002/jhet.5570430123
[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. Microwave in organic and medicinal chemistry, 2nd Edition, John Wiley & Sons, 2012.
https://doi.org/10.1002/9783527647828
[9]. Kiselev, V. D.; Kornilov, D. A.; Lekomtseva, I. I.; Konovalov, A. I. Int. J. Chem. Kinet. 2015, 47, 289-295.
https://doi.org/10.1002/kin.20908
[10]. Oliverio, M.; Costanzo, P.; Nardi, M.; Rivalta, I.; Procopio, A. ACS Sustain. Chem. Eng. 2014, 2(5), 1228-1233.
https://doi.org/10.1021/sc5000682
[11]. Alzaydi, K. M.; Abojabal, N. S.; Elnagdi, M. H. Tetrahedron Lett. 2016, 57, 3596-3599.
https://doi.org/10.1016/j.tetlet.2016.05.035
[12]. Al-Marzouq, D. S.; Zaky, O. S.; Alnajjar, A. A.; Sadek, K. U. Eur. J. Chem. 2016, 7, 347-351.
https://doi.org/10.5155/eurjchem.7.3.347-351.1473
[13]. Aziz, S. I.; Anwar, H. F.; Alapasery, M.; Elnagdi, M. H. J. Heterocyclic Chem. 2006, 42, 1-4.
https://doi.org/10.1007/s10593-006-0040-3
[14]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Elnagdi, M. H. Arkivoc 2006, 13, 147-157.
[15]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Hassaneen, H. M.; Elnagdi, M. H. J. Heterocyclic. Chem. 2007, 44, 1-4.
[16]. Al-Mousawi, S. M.; Moustafa, M. S.; Elnagdi, M. H. Tetrahedron Lett. 2009, 50, 4611-4613.
https://doi.org/10.1016/j.tetlet.2009.08.037
[17]. Ghozlan, S. A. S.; Abdelmoniem, A. M.; Butenschon, H.; Abdelhamid, I. A. Tetrahedron 2015, 71, 1413-1418.
https://doi.org/10.1016/j.tet.2015.01.026
[18]. Moustafa M. S.; Al-Mouswai, S. M.; Elnagdi, M. H. RSC Adv. 2016, 6, 90840-90845.
https://doi.org/10.1039/C6RA19535K
[19]. Abdelmoniem, A. M.; Abdelhamid, I. A. Curr. Org. Chem. 2016, 14, 1512-1546.
https://doi.org/10.2174/1385272820666160216224951
[20]. Sun, M.; Wu, X.; Chen, J.; Cao, M.; Ji, M. Eur. J. Med. Chem. 2010, 45, 2299-2306.
https://doi.org/10.1016/j.ejmech.2010.02.005
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.7.4.468-472.1508

















European Journal of Chemistry 2016, 7(4), 468-472 | doi: https://doi.org/10.5155/eurjchem.7.4.468-472.1508 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.