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Synthesis of 3-Chloro-3-(trimethylsilyl)prop-2-enoic Acid Amides and Hydrazides from 3-(Trimethylsilyl)propynoic Acid

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Abstract

A number of previously unknown and difficultly accessible polyfunctional β-chloro-β-(trimethyl­silyl)prop-2-enoic acid amides and hydrazides have been synthesized by amination of 3-chloro-3-(trimethyl­silyl)­prop-2-enoyl chloride with the corresponding amines, amino alcohols, 2-amino-4-methylpentanoic acid, and hydrazines. Initial 3-chloro-3-(trimethylsilyl)prop-2-enoyl chloride has been prepared by hydrohalogenation of 3-trimethylsilylpropynoic acid with thionyl chloride in DMF, followed by treatment with oxalyl chloride.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the Baikal joint analytical center, Siberian Branch, Russian Academy of Sciences.

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Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    M. V. Andreev, M. M. Demina, A. S. Medvedeva, L. P. Safronova, A. I. Albanov & A. V. Afonin

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  1. M. V. Andreev
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  2. M. M. Demina
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  3. A. S. Medvedeva
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  4. L. P. Safronova
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Correspondence to M. V. Andreev.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 4, pp. 550–561 https://doi.org/10.31857/S0514749221040108.

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Andreev, M.V., Demina, M.M., Medvedeva, A.S. et al. Synthesis of 3-Chloro-3-(trimethylsilyl)prop-2-enoic Acid Amides and Hydrazides from 3-(Trimethylsilyl)propynoic Acid. Russ J Org Chem 57, 565–574 (2021). https://doi.org/10.1134/S1070428021040102

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