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Related Concept Videos

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group.
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Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

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The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Modified Bohlmann-Rahtz Pyridine Synthesis for Cyclic Ketones.

Keita Ikeno1, Haruna Oku1, Kenta Rakumitsu1

  • 1Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 18, 2025
PubMed
Summary

Researchers developed a new pyridine synthesis method using ammonium fluoride and cyclic ketones. This approach offers mild conditions and broad substrate scope for creating cycloalkane-fused pyridines.

Keywords:
azaheliceneepiguaipyridinepyridinetotal synthesisBohlmann–Rahtz pyridine synthesis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The Bohlmann-Rahtz pyridine synthesis is a known method for creating trisubstituted pyridines.
  • Traditional methods require harsh conditions and highly reactive compounds like aminoacrylates or β-ketoesters.

Purpose of the Study:

  • To develop a milder and more efficient pyridine synthesis.
  • To explore the use of ammonium fluoride with cyclic ketones for pyridine formation.

Main Methods:

  • Reaction of various cyclic ketones with ammonium fluoride.
  • Optimization of reaction conditions for efficiency and selectivity.
  • Application of the developed method to synthesize natural products and functional molecules.

Main Results:

  • Efficient synthesis of cycloalkane-fused pyridines under mild conditions.
  • Demonstrated wide substrate generality and selectivity for cyclic ketones over aliphatic ketones.
  • Successful synthesis of epiguaipyridine and aza[5]helicene.

Conclusions:

  • Ammonium fluoride-mediated reaction of cyclic ketones provides a novel and efficient route to cycloalkane-fused pyridines.
  • The method offers advantages in terms of mild conditions and substrate scope compared to existing pyridine syntheses.
  • This new synthetic strategy is applicable to the preparation of complex molecules.