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Synthesis and Antibacterial Activity of N-Substituted 2-(Benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides

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Abstract

Previously unknown N-substituted 2-(benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides were synthesized by reaction of 2-imino-2,5-dihydrofuran-3-carboxamides with benzylamine in glacial acetic acid. It was found that a part of benzylamine reacts as a nucleophile at the imino group and that the other part undergoes oxidation followed by dehydration to generate benzylimine which acts as a synthetic equivalent of benzaldehyde toward the 4-methyl group. The synthesized compounds were characterized by IR and NMR spectra and elemental analyses. 2-(Benzylimino)-N,5,5-trimethyl-4-(2-phenylethenyl)-2,5-dihydrofuran-3-carboxamide was also synthesized independently by reaction of previously reported 2-imino-4-(2-phenylethenyl)-N,5,5-trimethyl-2,5-dihydrofuran-3-carboxamide with benzylamine in glacial acetic acid.

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ACKNOWLEDGMENTS

The authors thank the staff of the Molecular Structure Research Center (Yerevan, Armenia) for performing spectral studies and elemental analysis of the synthesized compounds.

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Authors and Affiliations

  1. Yerevan State University, 0025, Yerevan, Armenia

    L. V. Karapetyan & G. G. Tokmajyan

  2. Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Science of Armenia, 0014, Yerevan, Armenia

    H. M. Stepanyan

Authors
  1. L. V. Karapetyan
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  2. G. G. Tokmajyan
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  3. H. M. Stepanyan
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Corresponding author

Correspondence to L. V. Karapetyan.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1759–1765 https://doi.org/10.31857/S0514749221120119.

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Karapetyan, L.V., Tokmajyan, G.G. & Stepanyan, H.M. Synthesis and Antibacterial Activity of N-Substituted 2-(Benzylimino)-4-styryl-2,5-dihydrofuran-3-carboxamides. Russ J Org Chem 57, 1974–1978 (2021). https://doi.org/10.1134/S1070428021120113

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