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Vinylation of a Secondary Amine Core with Calcium Carbide for Efficient Post-Modification and Access to Polymeric Materials

Saint Petersburg State University, Universitetsky Prospect, 26, St. Petersburg 198504, Russia
Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Prospect, 47, Moscow 119991, Russia
Author to whom correspondence should be addressed.
Molecules 2018, 23(3), 648;
Received: 16 February 2018 / Revised: 9 March 2018 / Accepted: 9 March 2018 / Published: 13 March 2018
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
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We developed a simple and efficient strategy to access N-vinyl secondary amines of various naturally occurring materials using readily available solid acetylene reagents (calcium carbide, KF, and KOH). Pyrrole, pyrazole, indoles, carbazoles, and diarylamines were successfully vinylated in good yields. Cross-linked and linear polymers were synthesized from N-vinyl carbazoles through free radical and cationic polymerization. Post-modification of olanzapine (an antipsychotic drug substance) was successfully performed. View Full-Text
Keywords: acetylene; calcium carbide; vinylation; olanzapine; functionalization acetylene; calcium carbide; vinylation; olanzapine; functionalization

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Rodygin, K.S.; Bogachenkov, A.S.; Ananikov, V.P. Vinylation of a Secondary Amine Core with Calcium Carbide for Efficient Post-Modification and Access to Polymeric Materials. Molecules 2018, 23, 648.

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