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Synthesis of Nonracemic Tetrazole GABA Analogs

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Abstract

Nonracemic 3-substituted 4-(1H-tetrazol-1-yl)butanoic acids, analogs of the neurotropic drugs phenibut, tolibut, and baclofen, were synthesized by a three-component reaction of the R-isomers of the corresponding amino acids, triethyl orthoformate, and sodium azide. The key stage of the synthesis is the asymmetric addition of diethyl malonate to nitroalkenes, catalyzed by a Ni(II) complex of (S,S)-N,N′-dibenzylcyclohexane-1,2-diamine.

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Authors and Affiliations

  1. Samara State Technical University, ul. Molodogvardeiskaya 244, Samara, 443100, Russia

    A. N. Reznikov & Yu. N. Klimochkin

  2. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    V. A. Ostrovskii

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  1. A. N. Reznikov
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  2. V. A. Ostrovskii
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  3. Yu. N. Klimochkin
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Correspondence to Yu. N. Klimochkin.

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Original Russian Text © A.N. Reznikov, V.A. Ostrovskii, Yu.N. Klimochkin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1699–1704.

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Reznikov, A.N., Ostrovskii, V.A. & Klimochkin, Y.N. Synthesis of Nonracemic Tetrazole GABA Analogs. Russ J Org Chem 54, 1715–1721 (2018). https://doi.org/10.1134/S1070428018110155

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  • DOI: https://doi.org/10.1134/S1070428018110155

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