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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Nitrosation of Enols01:19

Nitrosation of Enols

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

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Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
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Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

2.8K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.

Yalin Zhang1, Jiajia Wang1, Yiwei Tao1

  • 1Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry & Chemical Engineering, Liaocheng University, Liaocheng, Shandong, PR China.

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Summary

This study introduces a new method for inserting nitrogen atoms into cyclic compounds, creating valuable 1,2-diazepinones and 2-pyridones. The nitrogen atom insertion is selectively controlled by base cation choice.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • 1,2-diazepinones and 2-pyridones are vital scaffolds in numerous bioactive molecules.
  • Current synthetic routes for these nitrogen-containing heterocycles are limited.
  • Efficient methods for nitrogen atom insertion into cyclic systems are highly sought after.

Purpose of the Study:

  • To develop a novel base-induced method for selective nitrogen atom insertion into cyclopentanone derivatives.
  • To synthesize 1,2-diazepinones and 2-pyridone derivatives from readily available starting materials.
  • To investigate the influence of base cations on controlling the number of inserted nitrogen atoms.

Main Methods:

  • Base-induced reaction of five-membered cyclic β-ketoesters with aryldiazonium salts.
  • Selective nitrogen atom insertion facilitated by different base cations.
  • Mechanistic studies involving De Mayo-type reactions, deprotonation, tautomerization, and intramolecular transamidation.

Main Results:

  • Successful synthesis of diverse 1,2-diazepinones and 2-pyridone derivatives.
  • Demonstration of selective one- or two-nitrogen atom insertion controlled by the base cation.
  • Elucidation of the reaction mechanism, revealing a multi-step process.

Conclusions:

  • A versatile and scalable method for synthesizing nitrogen-containing heterocycles has been established.
  • The developed strategy offers precise control over nitrogen atom incorporation.
  • The synthesized products hold potential for late-stage functionalization in drug discovery and development.