An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity
| Autor: | Abdel-Zaher A. Elassar |
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| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | European Journal of Chemistry. 6:387-393 |
| ISSN: | 2153-2257 2153-2249 |
| DOI: | 10.5155/eurjchem.6.4.387-393.1306 |
| Popis: | Tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines afforded in situ N -acylated amines, which undergoes cycloaddition reaction with other molecule of acid chloride to give dihydropyran carboxamide derivatives as an unexpected product. 2-Amino benzimidazole, 2-aminobenzthiazole, 2-aminothiazole, anthranilic acid, o -pheneylenediamine, and 3-methyl-1 H- pyrazol-5(4 H )-one are reacted with methacryloyl chloride at 0 °C to give different derivatives of dihydropyran carboxamide. The latter compound was obtained through acylation of the organic amines followed by tandem cycloaddition reaction. In contrast acryloyl chloride afforded only N -acylated derivatives. Both products are characterized by single crystal X-ray diffraction method. Bioactivity of the newly synthesized products was studied against Gram-positive, Gram-negative bacteria and fungus. |
| Databáze: | OpenAIRE |
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