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Reactions of 3-cyclopropyl-3-oxopropionitrile anion generated by electroreduction of 5-cyclopropylisoxazole

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Abstract

3-Cyclopropyl-3-oxopropionitrile anion obtained by cathodic reduction of 5-cyclopropylisoxazole in an aprotic medium was used as an example to demonstrate that cyano ketone anions show a dual reactivity. The reaction of acetyl chloride with the electrogenerated tetrabutylammonium salt of 3-cyclopropyl-3-oxopropionitrile gave O-acylation products, whereas the reaction with its sodium salt gives C-acylation products. The reactions of these salts with hydroxylamine hydrochloride follow a different route: in the case of the tetrabutylammonium salt, resinification takes place, while in the case of the sodium salt, 5-amino-3-cyclopropylisoxazole is formed. The condensation of this product with 4,4,4-trifluoro-1-(2-thienyl)butane-1,3-dione in glacial AcOH affords 3-cyclopropyl-6-(2-thienyl)-4-(trifluoromethyl)isoxazolo[5,4-b]pyridine in 85% yield.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. Petrosyan, S. V. Neverov & V. L. Sigacheva

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  1. V. A. Petrosyan
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  2. S. V. Neverov
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  3. V. L. Sigacheva
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Correspondence to V. A. Petrosyan.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2110–2114, November, 2007.

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Petrosyan, V.A., Neverov, S.V. & Sigacheva, V.L. Reactions of 3-cyclopropyl-3-oxopropionitrile anion generated by electroreduction of 5-cyclopropylisoxazole. Russ Chem Bull 56, 2184–2188 (2007). https://doi.org/10.1007/s11172-007-0343-2

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  • DOI: https://doi.org/10.1007/s11172-007-0343-2

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