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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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.


Keywords


Synthesis; Biological activity; Cycloaddition reaction; Single crystal structure; Tandem cycloaddition reaction; Dihydropyrancarboxamide derivatives

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DOI: 10.5155/eurjchem.6.4.387-393.1306

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Helwan University, Cairo, 11795, Egypt

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Elassar, A. Eur. J. Chem. 2015, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, A. An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity. Eur. J. Chem. 2015, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, A. (2015). An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity. European Journal of Chemistry, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, Abdel-Zaher. "An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity." European Journal of Chemistry [Online], 6.4 (2015): 387-393. Web. 31 May. 2020
Elassar, Abdel-Zaher. "An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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DOI Link: https://doi.org/10.5155/eurjchem.6.4.387-393.1306

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