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Nomenclature of Aryl and Heterocyclic Amines01:10

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Ulcerative colitis is a chronic inflammatory condition primarily affecting the colon and rectum. The primary drugs used in the treatment of ulcerative colitis are aminosalicylates. They exhibit anti-inflammatory and immunosuppressive properties. They modulate inflammatory mediators and inhibit the activity of nuclear factor κB (NF-κB). Aminosalicylates also reduce inflammation by inhibiting prostaglandin and leukotriene production and decreasing neutrophil chemotaxis and superoxide...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Preparation of 1° Amines: Azide Synthesis01:22

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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5-HT3 receptor antagonists, such as dolasetron, granisetron (Kytril), ondansetron (Zofran), and palonosetron (Axoli), are crucial in managing chemotherapy-induced nausea and vomiting (CINV) and postoperative nausea. These drugs selectively block 5-HT3 receptors in the visceral vagal and spinal afferent nerves, chemoreceptor trigger zone, and the vomiting center. They have a rapid onset of action and can be given as a single dose before chemotherapy. Ondansetron and granisetron, in particular,...
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Updated: Oct 31, 2025

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Cata-Annulated Azaacene Bisimides.

Maximilian Elter1, Lukas Ahrens1, Stella M Luo2

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 1, 2021
PubMed
Summary

Researchers synthesized ultra-electron-deficient azaacenes with record-low reduction potentials. These novel materials, featuring cata-annulated bisimide structures, exhibit ultrahigh electron affinities, paving the way for advanced electronic applications.

Keywords:
azaacenesbisimidesbutterfly dimerelectron acceptorsheteroacenes

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Area of Science:

  • Organic chemistry
  • Materials science
  • Supramolecular chemistry

Background:

  • Azaacenes are nitrogen-containing polycyclic aromatic hydrocarbons with unique electronic properties.
  • Developing materials with high electron affinity is crucial for organic electronics.

Purpose of the Study:

  • To synthesize novel ultra-electron-deficient azaacenes.
  • To investigate their electronic properties, particularly electron affinity and reduction potentials.

Main Methods:

  • Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide.
  • Oxidation of intermediate N,N'-dihydro compounds using manganese dioxide (MnO2) or lead dioxide (PbO2).

Main Results:

  • Successfully synthesized cata-annulated bisimide azaacenes.
  • Achieved ultrahigh electron affinities with first reduction potentials as low as -0.35 V for a tetraazapentacene.
  • Observed the formation of a symmetric butterfly dimer when attempting to synthesize a tetrakis(dicarboximide)tetraazaheptacene.

Conclusions:

  • The developed synthetic route enables access to novel azaacene derivatives with exceptionally low reduction potentials.
  • These compounds demonstrate potential for applications requiring strong electron-accepting materials.
  • The study highlights synthetic challenges and alternative structures in the pursuit of extended azaacene systems.