Novel One-Pot Cyclization Reactions: Synthesis of Pentasubstituted Cyclohexane Derivatives Containing Chiral Carbon Atoms

Two novel cyclohexane derivatives, [2,6-bis(4-chloro/bromophenyl)-4-hydroxy-4-(pyridin-2-yl)­cyclohexane-1,3-diyl]bis(pyridin-2-ylmethanones), were synthesized in one step from 2-acetylpyridine and 4-chloro- or 4-bromobenzaldehyde with high yield under mild conditions. The reaction sequence is likel...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 59; no. 1; pp. 196 - 201
Main Authors Liu, E., Jin, Z. S., Jian, F. F.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 2023
Springer Nature
Springer Nature B.V
Subjects
Chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Cyclohexane
Organic Chemistry
Physical Sciences
Science & Technology
X ray analysis
cyclization reaction
asymmetric carbon
one-pot reaction
X-ray analysis
cyclohexane
fluorescence properties
NANOPARTICLES
ACID
CRYSTAL-STRUCTURE
COMPLEXES
C-C
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Summary:Two novel cyclohexane derivatives, [2,6-bis(4-chloro/bromophenyl)-4-hydroxy-4-(pyridin-2-yl)­cyclohexane-1,3-diyl]bis(pyridin-2-ylmethanones), were synthesized in one step from 2-acetylpyridine and 4-chloro- or 4-bromobenzaldehyde with high yield under mild conditions. The reaction sequence is likely to include the formation of chalcone, Cannizzaro reaction, and one-pot cyclization, and this process represents a new strategy in cyclization reactions. The synthesized compounds showed fluorescence in the region λ 320–450 nm, and their structure was confirmed by spectroscopic data, as well as by X-ray analysis.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428023010220