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Related Concept Videos

Nitrosation of Enols01:19

Nitrosation of Enols

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.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Diaryl Ether Containing N-Hydroxycarbamates from Nitroso Cycloadducts.

Joshua Bolger1, Marvin Miller

  • 1Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556.

Tetrahedron Letters
|April 12, 2011
PubMed
Summary
This summary is machine-generated.

A novel copper-catalyzed reaction regioselectively opens nitroso cycloadducts to synthesize diaryl ethers. These compounds show potential as inhibitors of the proinflammatory enzyme 5-lipoxygenase.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • N-hydroxycarbamate derivatives are versatile synthetic intermediates.
  • Diaryl ethers are prevalent structural motifs in pharmaceuticals.
  • 5-lipoxygenase (5-LOX) is a key enzyme in inflammatory pathways.

Purpose of the Study:

  • To develop a regioselective method for synthesizing substituted diaryl ethers.
  • To explore the potential of these compounds as 5-lipoxygenase inhibitors.

Main Methods:

  • Copper-catalyzed allylic alkylation for regioselective ring opening of nitroso cycloadducts.
  • Synthesis of phenol intermediates via protected 3-hydroxybenzyl bromide.
  • Copper-mediated coupling with arylboronic acids to form diaryl ethers.
  • Alumina-promoted transcarbamoylation for final product formation.

Main Results:

  • Successful regioselective ring opening of N-hydroxycarbamate-derived nitroso cycloadducts.
  • Efficient synthesis of a series of substituted diaryl ether compounds.
  • Generation of late-stage phenol intermediates.
  • Demonstrated potential for inhibitory activity against 5-lipoxygenase.

Conclusions:

  • A new synthetic route to diaryl ethers was established.
  • The synthesized compounds warrant further investigation for their anti-inflammatory properties.
  • The methodology offers a valuable tool for accessing complex organic molecules.