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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.
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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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[2]. Fatma Ahmed Abo Elsoud, Mohamed Abd-Elmonem, Mohamed Abo Elsebaa, Kamal Usef Sadek
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[3]. Afaf Abdel Hamid, Mohamed Abd‐Elmonem, Alaa M. Hayallah, Fatma A. Abo Elsoud, Kamal U. Sadek
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[4]. Douaa Salman AlMarzouq, Noha M. Hilmy Elnagdi
Glycerol and Q-Tubes: Green Catalyst and Technique for Synthesis of Polyfunctionally Substituted Heteroaromatics and Anilines
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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
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DOI: 10.1007/s41061-020-00314-6
[6]. Majdah AL-Johani, Khadijah Al-Zaydi, Sameera Mousally, Norah Alqahtani, Noha Elnagdi, Mohamed Elnagdi
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DOI Link: https://doi.org/10.5155/eurjchem.7.4.468-472.1508
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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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