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

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Abstract

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.

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Funding

This work was financially supported by Henan University of Science and Technology (Luoyang City Talents Plan Fund).

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Authors and Affiliations

  1. School of Chemical Engineering and Pharmaceutics, Henan University of Science and Technology, 471023, Luoyang, China

    E. Liu, Z. S. Jin & F. F. Jian

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  1. E. Liu
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  2. Z. S. Jin
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  3. F. F. Jian
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Correspondence to F. F. Jian.

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Liu, E., Jin, Z.S. & Jian, F.F. Novel One-Pot Cyclization Reactions: Synthesis of Pentasubstituted Cyclohexane Derivatives Containing Chiral Carbon Atoms. Russ J Org Chem 59, 196–201 (2023). https://doi.org/10.1134/S1070428023010220

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