Elmesallamy, M., Assy, M., Selim, Y., Abd El-Azim, M. (2023). Novel heterocyclization process novel design of spiroazoles. Bulletin of Faculty of Science, Zagazig University, 2023(1), 164-168. doi: 10.21608/bfszu.2022.169353.1193
Maha Ahmed Elmesallamy; Mohamed G. Assy; Yasser Selim; Mohamed Abd El-Azim. "Novel heterocyclization process novel design of spiroazoles". Bulletin of Faculty of Science, Zagazig University, 2023, 1, 2023, 164-168. doi: 10.21608/bfszu.2022.169353.1193
Elmesallamy, M., Assy, M., Selim, Y., Abd El-Azim, M. (2023). 'Novel heterocyclization process novel design of spiroazoles', Bulletin of Faculty of Science, Zagazig University, 2023(1), pp. 164-168. doi: 10.21608/bfszu.2022.169353.1193
Elmesallamy, M., Assy, M., Selim, Y., Abd El-Azim, M. Novel heterocyclization process novel design of spiroazoles. Bulletin of Faculty of Science, Zagazig University, 2023; 2023(1): 164-168. doi: 10.21608/bfszu.2022.169353.1193
Novel heterocyclization process novel design of spiroazoles
2Chemistry Dep., Faculty of Science, Zagazig University, Zagazig, Egypt
3Faculty of Specific Education, Zagazig University
4Department of chemistry, faculty of science, Zagazig university
Abstract
When malono hydrazide 1 was allowed to react with benzaldehyde; the reaction yielded spiro compound 2. The reaction may start via formation of condensed product 2; followed by the addition of activated methylene to activated C=N. Also, condensation of the target 1 with cyclopentanone produced the non-isolable Schiff product 4 that underwent intramolecular cycloaddition reaction to form the spiro product 5. The addition of nucleophilic NH2 group of target 1 to heteroallene in basic medium resulted in triazole heterocyclization. The reaction may proceed via the formation of non-isolable thiosemicarbazide derivative 6; followed by intramolecular cyclization to furnish triazole derivative 7. Pyrazole derivative 8 underwent Michael addition with heteroallene providing fused triazole derivative 10 which may be formed through the non-isolable thiourea derivative. The target 8 underwent cycloaddition reaction with carbon disulphide to produce fused thiadiazole 12. Compound 8 underwent double nitrozation when treated with NaNO2/acetic acid yielding nitroso derivative 13.
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