European Journal of Chemistry 2011, 2(1), 51-57 | doi: https://doi.org/10.5155/eurjchem.2.1.51-57.249 | Get rights and content






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Studies with aza-heterocyclic N-oxides: Synthesis of some new aromatic N-oxide derivatives


Ahmed Ali Fadda (1) , Fathy Mohamed Abdelrazek (2,*) , Ahmed Mahmoud Fouda (3)

(1) Chemistry Department, Faculty of Science, Mansoura University, Mansoura, EG-35516, Egypt
(2) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(3) Chemistry Department, Faculty of Science, Mansoura University, Mansoura, EG-35516, Egypt
(*) Corresponding Author

Received: 16 Aug 2010 | Revised: 04 Oct 2010 | Accepted: 28 Oct 2010 | Published: 28 Mar 2011 | Issue Date: March 2011

Abstract


Benzofuroxan derivative (1a) reacts with the cyanoacetanilides (2a-d) to give the benzimidazole derivatives (3a-d). Benzofuroxan (1b) reacts with rhodanine derivatives (4a,b) in presence of sodium ethoxide to give the arylaminobenzoimidazole derivatives (6a,b); while the last reaction afforded the thiazolidinone derivatives (8a,b) and the o-benzoquinone dioxime derivatives (9a,b) when it was repeated in the presence of sodium acetate. Moreover, a series of quinoxalinyl 1,4-di-N-oxide derivatives were prepared starting from quinoxalin-1,4-di-N-oxide derivatives (10a-c). Plausible mechanisms to account for the formation of the products are discussed.

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Keywords


Heterocyclic N-oxides; Benzofuroxan; Rhodanine; o-Quinone dioximes; Thiocarbohydrazide; Curtius rearrangement

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DOI: 10.5155/eurjchem.2.1.51-57.249

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Funding information


Alexander von Humboldt Foundation (Germany), Institute of Organic Chemistry, TU-Dresden and Research fund of the Faculty of Science, Cairo University.

Citations

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[1]. Alaa A. Hassan, Maysa M. Makhlouf
Thiazolidine-4-ones from Thiocarbohydrazides
Journal of Heterocyclic Chemistry  55(11), 2480, 2018
DOI: 10.1002/jhet.3315
/


[2]. Yong Wang, Fu-de Ren, Duan-lin Cao
A dynamic and electrostatic potential prediction of the prototropic tautomerism between imidazole 3-oxide and 1-hydroxyimidazole in external electric field
Journal of Molecular Modeling  25(11), , 2019
DOI: 10.1007/s00894-019-4216-z
/


[3]. Sherihan A. El-Hadidy, Yasser A. Selim
New Synthetic Approaches for Cytotoxic Activity of Novel 1,8-Naphthyridine Derivatives
Journal of Heterocyclic Chemistry  55(1), 103, 2018
DOI: 10.1002/jhet.3011
/


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How to cite


Fadda, A.; Abdelrazek, F.; Fouda, A. Eur. J. Chem. 2011, 2(1), 51-57. doi:10.5155/eurjchem.2.1.51-57.249
Fadda, A.; Abdelrazek, F.; Fouda, A. Studies with aza-heterocyclic N-oxides: Synthesis of some new aromatic N-oxide derivatives. Eur. J. Chem. 2011, 2(1), 51-57. doi:10.5155/eurjchem.2.1.51-57.249
Fadda, A., Abdelrazek, F., & Fouda, A. (2011). Studies with aza-heterocyclic N-oxides: Synthesis of some new aromatic N-oxide derivatives. European Journal of Chemistry, 2(1), 51-57. doi:10.5155/eurjchem.2.1.51-57.249
Fadda, Ahmed, Fathy Mohamed Abdelrazek, & Ahmed Mahmoud Fouda. "Studies with aza-heterocyclic N-oxides: Synthesis of some new aromatic N-oxide derivatives." European Journal of Chemistry [Online], 2.1 (2011): 51-57. Web. 25 Oct. 2020
Fadda, Ahmed, Abdelrazek, Fathy, AND Fouda, Ahmed. "Studies with aza-heterocyclic N-oxides: Synthesis of some new aromatic N-oxide derivatives" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

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DOI Link: https://doi.org/10.5155/eurjchem.2.1.51-57.249

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