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Synthesis of some novel pyridine and naphthyridine derivatives
Fathy Mohamed Abdelrazek (1,*)
, Nazmi Abdel-Latif Kassab (2) , Nadia Hanafy Metwally (3) , Nehal Ahmed Sobhy (4) (1) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(2) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(3) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(4) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(*) Corresponding Author
Received: 09 May 2010 | Accepted: 11 Aug 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
2-[1-(Furan- or thiophen-2-yl)ethylidene)malononitriles (1a,b) undergo dimerization reactions in ethanol catalyzed by sodium ethoxide to afford 2-[4,6-di(furan- or thiophen-2-yl)-3-cyano-6-methyl-5,6-dihydropyridin-2(1H)-ylidene]malononitrile derivatives (2a,b), respectively. Compounds 2a and 2b couple with arene diazonium salts (3a-c) to afford the hydrazo derivatives (4a-f). They react also with hydrazines (5a,b) to afford the pyrazolo[3,4-H][1,6]naphthyridine derivatives (6a-d) and with urea derivatives (7a-c) to afford the pyrimido[4,5-H][1,6]naphthyridine derivatives (8a-f), respectively.
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DOI: 10.5155/eurjchem.1.4.368-372.104
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Funding information
Cairo University Research Fund.
Citations
[1]. Fathy M. Abdelrazek, Sobhi M. Gomha, Hassan M. Abdel‐aziz, Mohamed S. Farghaly, Peter Metz, Ahmed Abdel‐Shafy
Efficient synthesis and In Silico study of some novel pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine derivatives
Journal of Heterocyclic Chemistry 57(4), 1759, 2020
DOI: 10.1002/jhet.3901
[2]. Fathy M. Abdelrazek, Sobhi M. Gomha, Mohamed E.B. Shaaban, Kamal A. Rabee, Heba N. El-Shemy, Abanoub M. Abdallah, Peter Metz
One-Pot Three-Component Synthesis and Molecular Docking of Some Novel 2-Thiazolyl Pyridines as Potent Antimicrobial Agents
Mini-Reviews in Medicinal Chemistry 19(6), 527, 2019
DOI: 10.2174/1389557518666181019124104
[3]. Bin-Bin Feng, Rong-Zhang Jin, Mei-Mei Zhang, Xiang-Shan Wang
Green Synthesis of Spiro[indoline-3,4′-pyrazolo[3,4-b][1,6]naphthyridine]-2,5′(1′H)-diones Catalyzed by TsOH in Ionic Liquids
Journal of Heterocyclic Chemistry 53(5), 1578, 2016
DOI: 10.1002/jhet.2466
[4]. Sobhi M. Gomha, Fathy M. Abdelrazek, Aly H. Abdelrahman, Peter Metz
Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents
HETEROCYCLES 92(5), 954, 2016
DOI: 10.3987/COM-16-13443
[5]. Nadia H. Metwally, Fathy M. Abdelrazek, Salwa M. Eldaly
Synthesis and anticancer activity of some new heterocyclic compounds based on 1-cyanoacetyl-3,5-dimethylpyrazole
Research on Chemical Intermediates 42(2), 1071, 2016
DOI: 10.1007/s11164-015-2074-6
[6]. Paramita Das, Tandrima Chaudhuri, Chhanda Mukhopadhyay
Pseudo-Five-Component Domino Strategy for the Combinatorial Library Synthesis of [1,6] Naphthyridines—An On-Water Approach
ACS Combinatorial Science 16(11), 606, 2014
DOI: 10.1021/co400162m
[7]. Victor V. Dotsenko, Sergey G. Krivokolysko, Aminat M. Semenova
Heterocyclization reactions using malononitrile dimer (2-aminopropene-1,1,3-tricarbonitrile)
Chemistry of Heterocyclic Compounds 54(11), 989, 2018
DOI: 10.1007/s10593-018-2383-y
[8]. Man-Su Tu, Ying Li, Xiang Wang, Bo Jiang, Shu-Liang Wang, Shu-Jiang Tu
Regioselective [5 + 1] rearrangement–annulation: a new and efficient domino route to highly functionalized [1,6]naphthyridines
RSC Advances 3(12), 3877, 2013
DOI: 10.1039/c3ra22328k
[9]. Fathy M. Abdelrazek, Nadia H. Metwally, Nazmi A. Kassab, Mohammed T. Jaafar, Peter Metz, Anne Jäger
Studies on the Reaction of Cycloalkanones with Malonodinitrile
Journal of Heterocyclic Chemistry 51(6), 1785, 2014
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[10]. Rima D. Alharthy, Faisal Rashid, Abida Ashraf, Zahid Shafiq, Steven Ford, Mariya al-Rashida, Muhammad Yaqub, Jamshed Iqbal
Pyrazole derivatives of pyridine and naphthyridine as proapoptotic agents in cervical and breast cancer cells
Scientific Reports 13(1), , 2023
DOI: 10.1038/s41598-023-32489-5
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DOI Link: https://doi.org/10.5155/eurjchem.1.4.368-372.104
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