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Synthesis of Hybrid Compounds on the Basis of 4-[(1-Oxo-3,4-dihydro-2H-naphthalen-2-ylidene)methyl]benzoic acid

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Abstract

The reactions of 4-[(1-oxo-3,4-dihydro-2H-naphmalen-2-ylidene)methyl]benzoic acid with 3-(1,3-dioxobutane-1-yl)-2H-chromen-2-one in the presence of nitrogenous bases (piperidine, triethylamine or pyridine) were used to synthesize for the first time hybrid systems containing the pharmacophoric fragments of the reagents. The reaction scheme involves formation of a condensed dihydropyran structure and its subsequent aromatization into a benzodihydrochromenilium salt under the action of HCl. The process may be accompanied by the competing addition of an azanucleophile by the double bond of the chalcone.

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Authors and Affiliations

  1. Institute of Chemistry, Chernyshevskii National Research Saratov State University, ul. Astrakhanskaya 83, Saratov, 410012, Russia

    A. L. Ivanova, I. V. Kanevskaya & O. V. Fedotova

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  1. A. L. Ivanova
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  2. I. V. Kanevskaya
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  3. O. V. Fedotova
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Correspondence to A. L. Ivanova.

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The authors declare no conflict of interest.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 8, pp. 1287–1290.

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Ivanova, A.L., Kanevskaya, I.V. & Fedotova, O.V. Synthesis of Hybrid Compounds on the Basis of 4-[(1-Oxo-3,4-dihydro-2H-naphthalen-2-ylidene)methyl]benzoic acid. Russ J Org Chem 55, 1231–1233 (2019). https://doi.org/10.1134/S1070428019080244

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  • DOI: https://doi.org/10.1134/S1070428019080244

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