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Related Concept Videos

Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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

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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.
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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D-Hexopyranosides with Vicinal Nitrogen-Containing Functionalities.

Jana Pospíšilová1, Daniel Toman1, Tomáš Ručil1

  • 1Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, 77900 Olomouc, Czech Republic.

Molecules (Basel, Switzerland)
|August 10, 2024
PubMed
Summary

This review summarizes the synthesis of D-hexopyranosides containing nitrogen. These compounds are vital in natural products and pharmaceuticals due to their diverse biological activities.

Keywords:
D-hexopyranosidesMichael additionactivated hydroxyl groupaminoglycoside antibioticsaziridine ring-openingglucosamineneuraminidase inhibitorsnitrogen-containing functionalities

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • D-hexopyranosides with nitrogen functionalities are key components of natural products and pharmaceuticals.
  • Their structural complexity underlies a wide range of biological functions and activities.
  • These derivatives are subjects of extensive research interest.

Purpose of the Study:

  • To provide a comprehensive review of synthetic strategies for D-hexopyranosides with vicinal nitrogen-containing functionalities.
  • To cover synthetic advancements since the 1960s.
  • To organize syntheses based on substitution patterns and relative configurations.

Main Methods:

  • Literature review of synthetic methodologies for nitrogen-containing D-hexopyranosides.
  • Classification of synthetic routes based on the positions of substituents.
  • Analysis of methods concerning the relative configuration of vicinal functionalities.

Main Results:

  • Compilation of synthetic approaches for D-hexopyranosides with vicinal nitrogen functionalities.
  • Organization of synthetic data by substitution patterns and stereochemistry.
  • Overview of methodologies employed since the emergence of relevant research in the 1960s.

Conclusions:

  • The synthesis of nitrogen-containing D-hexopyranosides has evolved significantly since the 1960s.
  • Understanding synthetic routes is crucial for accessing diverse biologically active carbohydrate derivatives.
  • This review serves as a valuable resource for researchers in carbohydrate chemistry and drug discovery.