European Journal of Chemistry 2014, 5(3), 475-480 | doi: https://doi.org/10.5155/eurjchem.5.3.475-480.1050 | Get rights and content

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Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine


Mohanad Yakdhan Saleh (1,*) , Ala Ismael Ayoub (2)

(1) Department of Chemistry, College of Education for Pure Sciences, University of Mosul, 41002, Mosul, Iraq
(2) Department of Chemistry, College of Sciences, University of Mosul, 41002, Mosul, Iraq
(*) Corresponding Author

Received: 13 Mar 2014 | Revised: 24 Apr 2014 | Accepted: 04 May 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


A simple and regioselective synthesis of 2-chloro-3-formyl-1,8-naphthyridine, through Vilsmeier-Haack cyclization of N-(pyridin-2-yl)acetamide has been reported. The reaction of 2-chloro-3-formyl-1,8-naphthyridine is also investigated and new series of 1,8-naphthyridine derivatives such as 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-(phenylamino)azetidin-2-one, 3-chloro-4-(2-chloro-1,8-naphthyridin-3yl)-1-((4-nitrophenyl) amino)-azetidin-2-one and 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-((2,4-dinitrophenyl) amino)-azetidin-2-one have been prepared. The formyl group in the 1,8-naphthyridine is subjected to further transformation into alkoxy carbonyl (NIS-K2CO3/alcohol) to afford 3-alkoxy carbonyl-1,8-naphthyridine and new hetero cyclic compounds such as oxadiazolo, thiadiazolo-thion and triazolo-thion have been prepared. The reaction between 2-chloro-3-formyl-1,8-naphthyridine and sodium sulphide in DMF produced 2-mercapto-3-formyl-1,8-naphthyridine. Some of the prepared compounds were found to have good biological activity against Staphylococcus aureus and Staphylococcus epidermidis.


Keywords


Triazol; Thiadizol; Azetidine; Oxadiazol; Naphthyridine; Vilsmeier-Haack

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DOI: 10.5155/eurjchem.5.3.475-480.1050

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Funding information


Department of Chemistry, Eskisehir Osmangazi University, Eskisehir, Turkey and Department of Biology, Mosul University, 41002, Mosul, Iraq

Citations

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[1]. I.I. Levina, A.A. Gridnev
Practical Synthesis of 1,8-Naphthyridine-2,7-dialdehydes Syntone
Asian Journal of Chemistry  31(11), 2596, 2019
DOI: 10.14233/ajchem.2019.22229
/


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How to cite


Saleh, M.; Ayoub, A. Eur. J. Chem. 2014, 5(3), 475-480. doi:10.5155/eurjchem.5.3.475-480.1050
Saleh, M.; Ayoub, A. Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine. Eur. J. Chem. 2014, 5(3), 475-480. doi:10.5155/eurjchem.5.3.475-480.1050
Saleh, M., & Ayoub, A. (2014). Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine. European Journal of Chemistry, 5(3), 475-480. doi:10.5155/eurjchem.5.3.475-480.1050
Saleh, Mohanad, & Ala Ismael Ayoub. "Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine." European Journal of Chemistry [Online], 5.3 (2014): 475-480. Web. 28 Nov. 2021
Saleh, Mohanad, AND Ayoub, Ala. "Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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