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Peculiarities of three-component cyclization of ethyl 4,4,4-trifluoroacetoacetate and 1,2-ethanediamines with 3-methylbutan-2-one
Authors:Goryaeva  M V  Kushch  S O  Burgart  Ya V  Saloutin  V I
Institution: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
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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 hexahydroimidazo1,2-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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