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Reactions of Malononitrile with Cross-conjugated Dienone Derivatives of Cyclohexane. Synthesis of Substituted Partially Hydrogenated Quinoline- and Chromenecarbonitriles

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Abstract

The condensation of malononitrile with unsymmetrical dienones of the cyclohexane series under basic conditions selectively afforded substituted tetrahydroquinolinecarbonitriles. The reaction of 2,6-bis-(3-nitrophenylmethylidene)cyclohexan-1-one with malononitrile under similar conditions led to the formation of substituted tetrahydrochromenecarbonitrile. Factors determining the reaction direction and selectivity were discussed. The structure of the newly synthesized compounds was confirmed by IR and 1H NMR spectra.

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Authors and Affiliations

  1. Institute of Chemistry, Chernyshevskii Saratov National State Research University, Saratov, Russia

    N. O. Vasilkova, N. O. Vasilkova, A. S. Kalugina, A. V. Nikulin & A. P. Krivenko

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  1. N. O. Vasilkova
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  2. A. S. Kalugina
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  3. A. V. Nikulin
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  4. A. P. Krivenko
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Corresponding author

Correspondence to N. O. Vasilkova.

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Conflict of Interests

The authors declare no conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1098–1102.

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Vasilkova, N.O., Kalugina, A.S., Nikulin, A.V. et al. Reactions of Malononitrile with Cross-conjugated Dienone Derivatives of Cyclohexane. Synthesis of Substituted Partially Hydrogenated Quinoline- and Chromenecarbonitriles. Russ J Org Chem 55, 995–998 (2019). https://doi.org/10.1134/S1070428019070145

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  • DOI: https://doi.org/10.1134/S1070428019070145

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