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New Differently Functionalized Cyclopentenediones

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Abstract

2-Allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione reacted with highly nucleophilic secondary (diethylamine, morpholine, N-methylpiperazine, piperidine) and primary amines (allylamine) under mild conditions (methanol, 20°C, 24 h) to give products of substitution of the 4-chlorine atom in 60–87% yield. The reaction of the same compound with a weak nitrogen nucleophile, imidazole, afforded 4-(1H-imidazol-1-yl) derivative in a low yield (25%). Methionine methyl ester hydrochloride failed to react with 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione in methanolic potassium hydroxide; instead, 55% of 2-allyl-2-chloro-4-methoxy-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione was obtained. The reaction with methyl 2-sulfanylacetate in the presence of sodium hydride produced methyl {[4-allyl-4-chloro-3,5-dioxo-2-(2,4,6-trimethoxyphenyl)cyclopent-1-en-1-yl]sulfanyl}acetate in 47% yield.

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Acknowledgments

The spectral and analytical data were obtained using the equipment of the Chemistry Joint Center (Ufa Institute of Chemistry, Russian Academy of Sciences) and Agidel Joint Center (Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment (project no. AAAA-A17-117011910032-4).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, 450054, Russia

    V. A. Egorov, L. S. Khasanova, F. A. Gimalova & M. S. Miftakhov

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  1. V. A. Egorov
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  2. L. S. Khasanova
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  3. F. A. Gimalova
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  4. M. S. Miftakhov
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Corresponding author

Correspondence to M. S. Miftakhov.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1877–1882.

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Egorov, V.A., Khasanova, L.S., Gimalova, F.A. et al. New Differently Functionalized Cyclopentenediones. Russ J Org Chem 55, 1869–1873 (2019). https://doi.org/10.1134/S1070428019120091

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  • DOI: https://doi.org/10.1134/S1070428019120091

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