Direct Synthesis of Deuterium-Labeled O-, S-, N-Vinyl Derivatives from Calcium Carbide

Maria S. Ledovskaya; Vladimir V. Voronin; Konstantin S. Rodygin; Alexandra V. Posvyatenko; Ksenia S. Egorova; Valentine P. Ananikov

doi:10.1055/s-0037-1611518

Synthesis, Table of Contents

Synthesis 2019; 51(15): 3001-3013
DOI: 10.1055/s-0037-1611518

paper

Direct Synthesis of Deuterium-Labeled O-, S-, N-Vinyl Derivatives from Calcium Carbide

Maria S. Ledovskaya

^aInstitute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation

,

Vladimir V. Voronin

^aInstitute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation

,

Konstantin S. Rodygin

^aInstitute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation

^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation Email: val@ioc.ac.ru

,

Alexandra V. Posvyatenko

^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation Email: val@ioc.ac.ru

^cInstitute of Gene Biology, Russian Academy of Sciences, Vavilova str. 34/5, Moscow 119334, Russian Federation

^dDmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Ministry of Health of Russian Federation, Samory Mashela str., Moscow 117198, Russian Federation

,

Ksenia S. Egorova

^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation Email: val@ioc.ac.ru

,

Valentine P. Ananikov *

^aInstitute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation

^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation Email: val@ioc.ac.ru

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Abstract

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Abstract

A novel methodology for the preparation of trideuterovinyl derivatives of high purity directly from alcohols, thiols, and NH-compounds was developed. Commercially available calcium carbide and D₂O acted as a D₂-acetylene source, and DMSO-d ₆ was used to complete the formation of the D₂C=C(D)–X fragment (X = O, S, N). Polymerization of a selected trideuterovinylated compound showed a very promising potential of these substances in the synthesis of labeled polymeric materials. Biological activity of the synthesized trideuterovinyl derivatives was evaluated and the results indicated a significant increase of cytotoxicity upon deuteration.

Key words

deuterium labeling - deuteration - deuterated drugs - vinylation - calcium carbide

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References

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