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Synthesis 2019; 51(15): 3001-3013
DOI: 10.1055/s-0037-1611518
paper
© Georg Thieme Verlag Stuttgart · New York

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

Maria S. Ledovskaya
a   Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation
,
Vladimir V. Voronin
a   Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation
,
Konstantin S. Rodygin
a   Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation
b   N. 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
b   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation   Email: val@ioc.ac.ru
c   Institute of Gene Biology, Russian Academy of Sciences, Vavilova str. 34/5, Moscow 119334, Russian Federation
d   Dmitry 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
b   N. 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  *
a   Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russian Federation
b   N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russian Federation   Email: val@ioc.ac.ru
› Author AffiliationsWe gratefully acknowledge the support from the Russian Science Foundation (Project No. 18-13-00116).
Further Information

Publication History

Received: 18 March 2019

Accepted after revision: 22 March 2019

Publication Date:
30 April 2019 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611518.
  • Supporting Information
 

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