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Peculiarities of three-component cyclization of ethyl 4,4,4-trifluoroacetoacetate and 1,2-ethanediamines with 3-methylbutan-2-one

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Abstract

The peculiarities of the three-component cyclization of ethyl 4,4,4-trifluoroacetoacetate and 1,2-ethanediamines with 3-methylbutan-2-one into hexahydroimidazo[1,2-a]pyridin-5-ones were studied. The reactions proceeded under mild conditions. The use of methyl ketone with a bulky isopropyl substituent increased the stereoselectivity of the transformations, but the reaction with 1,2-diaminopropane was accompanied by the formation 4-[(1-ammoniopropan-2-yl)amino]-1,1,1-trifluoro-4-oxobut-2-en-2-olate as a by-product.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620990, Ekaterinburg, Russian Federation

    M. V. Goryaeva, S. O. Kushch, Ya. V. Burgart & V. I. Saloutin

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  1. M. V. Goryaeva
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  2. S. O. Kushch
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  3. Ya. V. Burgart
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  4. V. I. Saloutin
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Correspondence to V. I. Saloutin.

Additional information

This work was financially supported by the Russian Foundation for Basic Research (Project No. 18-03-00342) and in the framework of the Russian state assignment (Topic No. AAAA-A19-119011790132-7). Analytical studies were carried out using the equipment of the Centre for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2163—2166, November, 2020.

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Goryaeva, M.V., Kushch, S.O., Burgart, Y.V. et al. Peculiarities of three-component cyclization of ethyl 4,4,4-trifluoroacetoacetate and 1,2-ethanediamines with 3-methylbutan-2-one. Russ Chem Bull 69, 2163–2166 (2020). https://doi.org/10.1007/s11172-020-3016-z

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  • DOI: https://doi.org/10.1007/s11172-020-3016-z

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