期刊
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
卷 59, 期 3, 页码 376-382出版社
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428023030041
关键词
Schiff bases; N-nucleophiles; electron-deficient tertiary propargyl alcohols; 1; 3-dipoles; 3-oxazolidines
Schiff bases reacted with cyanopropargyl alcohols under catalyst-free and solvent-free conditions (80 degrees 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.
Schiff bases reacted with cyanopropargyl alcohols under catalyst-free and solvent-free conditions (80 degrees 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.
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