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An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity
Abdel-Zaher Abdel-Aziz Elassar (1,*)
(1) Chemistry Department, Faculty of Science, Ain Helwan, Helwan University, Cairo, 11795, Egypt
(*) Corresponding Author
Received: 20 Jul 2015 | Accepted: 22 Aug 2015 | Published: 31 Dec 2015 | Issue Date: December 2015
Abstract
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-1H-pyrazol-5(4H)-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.
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DOI: 10.5155/eurjchem.6.4.387-393.1306
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DOI Link: https://doi.org/10.5155/eurjchem.6.4.387-393.1306
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European Journal of Chemistry 2015, 6(4), 387-393 | doi: https://doi.org/10.5155/eurjchem.6.4.387-393.1306 | Get rights and content
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