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






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Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube


Kamal Usef Sadek (1,*) , Maghraby Ali Selim (2) , Abdul-Aziz Alnajjar (3) , Mohamed Atallah (4) , Mohamed Hilmy Elnagdi (5)

(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.


Keywords


Q-Tubes; Azaenamines; Arylhydrazonals; Biphenyl derivatives; Pyridazino naphthyridine; Reactions under high pressure

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DOI: 10.5155/eurjchem.7.4.468-472.1508

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Funding information


Minia University, 61519, Minia, Egypt and College of Technological Studies, Public Authority for Applied Education and Training, 13060, Safat, Kuwait

Citations

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[1]. 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
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DOI: 10.5155/eurjchem.10.2.166-170.1851
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[2]. 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
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[3]. 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
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[4]. 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
/


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How to cite


Sadek, K.; Selim, M.; Alnajjar, A.; Atallah, M.; Elnagdi, M. Eur. J. Chem. 2016, 7(4), 468-472. doi:10.5155/eurjchem.7.4.468-472.1508
Sadek, K.; Selim, M.; Alnajjar, A.; Atallah, M.; Elnagdi, M. Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube. Eur. J. Chem. 2016, 7(4), 468-472. doi:10.5155/eurjchem.7.4.468-472.1508
Sadek, K., Selim, M., Alnajjar, A., Atallah, M., & Elnagdi, M. (2016). Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube. European Journal of Chemistry, 7(4), 468-472. doi:10.5155/eurjchem.7.4.468-472.1508
Sadek, Kamal, Maghraby Ali Selim, Abdul-Aziz Alnajjar, Mohamed Atallah, & Mohamed Hilmy Elnagdi. "Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube." European Journal of Chemistry [Online], 7.4 (2016): 468-472. Web. 10 Apr. 2020
Sadek, Kamal, Selim, Maghraby, Alnajjar, Abdul-Aziz, Atallah, Mohamed, AND Elnagdi, Mohamed. "Multicomponent reactions under increased pressure: on the reaction of arylhydrazonals, aromatic aldehydes and malononitrile in Q-Tube" European Journal of Chemistry [Online], Volume 7 Number 4 (31 December 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.4.468-472.1508

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