European Journal of Chemistry 2010, 1(4), 368-372 | doi: https://doi.org/10.5155/eurjchem.1.4.368-372.104 | Get rights and content

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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.

1_4_368_372_800


Keywords


Fur-2-ylethylidenemalononitrile; Thien-2-ylethylidenemalononitrile; Dihydro-pyridines; Pyrazolo-naphthyridines; Pyrimido-naphthyridines

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DOI: 10.5155/eurjchem.1.4.368-372.104

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Funding information


Cairo University Research Fund.

Citations

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[1]. Fathy M. Abdelrazek, Sobhi M. Gomha, Hassan M. Abdel‐aziz, Mohamed S. Farghaly, Peter Metz, Ahmed Abdel‐Shafy
Efficient synthesis andIn Silicostudy 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
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[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
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[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
DOI: 10.1002/jhet.1883
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How to cite


Abdelrazek, F.; Kassab, N.; Metwally, N.; Sobhy, N. Eur. J. Chem. 2010, 1(4), 368-372. doi:10.5155/eurjchem.1.4.368-372.104
Abdelrazek, F.; Kassab, N.; Metwally, N.; Sobhy, N. Synthesis of some novel pyridine and naphthyridine derivatives. Eur. J. Chem. 2010, 1(4), 368-372. doi:10.5155/eurjchem.1.4.368-372.104
Abdelrazek, F., Kassab, N., Metwally, N., & Sobhy, N. (2010). Synthesis of some novel pyridine and naphthyridine derivatives. European Journal of Chemistry, 1(4), 368-372. doi:10.5155/eurjchem.1.4.368-372.104
Abdelrazek, Fathy, Nazmi Abdel-Latif Kassab, Nadia Hanafy Metwally, & Nehal Ahmed Sobhy. "Synthesis of some novel pyridine and naphthyridine derivatives." European Journal of Chemistry [Online], 1.4 (2010): 368-372. Web. 24 Oct. 2021
Abdelrazek, Fathy, Kassab, Nazmi, Metwally, Nadia, AND Sobhy, Nehal. "Synthesis of some novel pyridine and naphthyridine derivatives" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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