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Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones

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Abstract

The reactions of 2-perfluoroacyl-1H-benzo[f]chromenes and 6,7-dimethyl-3-trifluoroacetyl-4H-chromene with primary aliphatic amines and ammonia afforded a series of enamino ketones containing a (2-hydroxynaphthalen-1-yl)methyl or 2-hydroxybenzyl substituent in the α-position with respect to the carbonyl group. These reactions involved opening of the pyran ring, which followed aza-Michael addition as the initial step. The obtained enamino ketones were found to exist in DMSO solution as single E isomers.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the “Study of Physicochemical Properties of Substances and Materials” joint center at the Samara State Technical University.

Funding

This study was performed under financial support by the Russian Science Foundation (project no. 19-73-10109).

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Authors and Affiliations

  1. Samara State Technical University, 443100, Samara, Russia

    V. A. Osyanin, K. S. Korzhenko, D. A. Rashchepkina, D. V. Osipov & Yu. N. Klimochkin

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  1. V. A. Osyanin
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  2. K. S. Korzhenko
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  3. D. A. Rashchepkina
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  4. D. V. Osipov
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  5. Yu. N. Klimochkin
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Correspondence to V. A. Osyanin.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 949–960 https://doi.org/10.31857/S0514749221070041.

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Osyanin, V.A., Korzhenko, K.S., Rashchepkina, D.A. et al. Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones. Russ J Org Chem 57, 1053–1062 (2021). https://doi.org/10.1134/S1070428021070046

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