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Cyclopropanation of N-substituted 3-aryl-2-cyanoprop-2-enamides and derivatives of 5,5-Dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid and 2-oxochromene-3-carboxylic acid with bromine-containing zinc enolates

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Abstract

Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-substituted 3-aryl-2-cyanoprop-2-enamides and 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic and 2-oxochromene-3-carboxylic acid derivatives to give, respectively, N-substituted 2-alkyl-3-aryl-2-aroyl-1-cyanocyclopropane-1-carboxamides, 6-(4-bromobenzoyl)-4,4,6-trimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester and morpholide, and 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropla[c]chromene-1a-carboxylic acids as a single geometric isomer. Treatment of 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxylic acids with carboxylic acid anhydrides leads to the formation of the corresponding 9c-alkyl-1-aryl-3,4-dioxo-9b,9c-dihydro-2,5-dioxacyclopenta[2,3]cyclopropa[1,2-a]naphthalen-1-yl carboxylates.

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References

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Authors and Affiliations

  1. Perm State University, ul. Bukireva 15, Perm, 614990, Russia

    V. V. Shchepin, P. S. Silaichev, Yu. G. Stepanyan, M. M. Kalyuzhnyi & N. Yu. Russkikh

  2. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia

    M. I. Kodess

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  1. V. V. Shchepin
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  2. P. S. Silaichev
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  3. Yu. G. Stepanyan
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  4. M. M. Kalyuzhnyi
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  5. N. Yu. Russkikh
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Original Russian Text © V.V. Shchepin, P.S. Silaichev, Yu.G. Stepanyan, M.M. Kalyuzhnyi, N.Yu. Russkikh, M.I. Kodess, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 993–1000.

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Shchepin, V.V., Silaichev, P.S., Stepanyan, Y.G. et al. Cyclopropanation of N-substituted 3-aryl-2-cyanoprop-2-enamides and derivatives of 5,5-Dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylic acid and 2-oxochromene-3-carboxylic acid with bromine-containing zinc enolates. Russ J Org Chem 42, 973–980 (2006). https://doi.org/10.1134/S1070428006070086

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  • DOI: https://doi.org/10.1134/S1070428006070086

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