Novel heterocyclization process novel design of spiroazoles | ||
| Bulletin of Faculty of Science, Zagazig University | ||
| Article 14, Volume 2023, Issue 1, March 2023, Pages 164-168 PDF (840.1 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/bfszu.2022.169353.1193 | ||
| Authors | ||
| Maha Ahmed Elmesallamy* 1; Mohamed G. Assy2; Yasser Selim3; Mohamed Abd El-Azim4 | ||
| 1Chemistry/ faculty of science/ benha univeristy | ||
| 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. | ||
| Keywords | ||
| Hydrazide; spiropyrazole; pyrazolo triazole; pyrazole thiadiazole; nitrosopyrazole | ||
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