Uncatalyzed Reactions of Schiff Bases with Cyanopropargyl Alcohols. Synthesis of Functionalized 1,3-Oxazolidines

Schiff bases reacted with cyanopropargyl alcohols under catalyst-free and solvent-free conditions (80°C, 10–12 h) to give functionalized 1,3-oxazolidines in up to 82% yield. The reaction involves a sequence of transformations, which includes the formation of a 1,3-dipolar intermediate via addition o...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2023-03, Vol.59 (3), p.376-382
Main Authors: Oparina, L. A., Grishchenko, L. A., Kolyvanov, N. A., Ushakov, I. A., Trofimov, B. A.
Format: Article
Language:English
Subjects:
Alcohols
Chemistry
Chemistry and Materials Science
Imines
Nucleophiles
Organic Chemistry
Oxazolidine
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Summary:Schiff bases reacted with cyanopropargyl alcohols under catalyst-free and solvent-free conditions (80°C, 10–12 h) to give functionalized 1,3-oxazolidines in up to 82% yield. The reaction involves a sequence of transformations, which includes the formation of a 1,3-dipolar intermediate via addition of the neutral N-nucleophile to the activated triple bond, proton transfer from the hydroxy group to the carbanionic center of that intermediate, and intramolecular attack of the oxygen-centered anion on the former C=N carbon atom of Schiff base with closure of 1,3-oxazolidine ring.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023030041