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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:29

Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:22

Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

Cholinergic agonists or cholinomimetics mimic the action of acetylcholine to stimulate the parasympathetic nervous system. They are categorized into direct-acting and indirect-acting agents. The direct-acting cholinergic drugs induce the parasympathetic response by directly binding to the muscarinic or nicotine receptors. In comparison, the indirect-acting cholinergic drugs prevent acetylcholine hydrolysis, indirectly contributing to the extended parasympathetic response.
The direct-acting...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.

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Crystal structures of three homologues with increasing ring size: 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8-tetra-hydro-quinoline-3-carbo-nitrile, 2-meth-oxy-4-(thio-phen-2-yl)-6,7,8,9-tetra-hydro-5<i>H</i>-cyclo-hepta-[<i>b</i>]pyridine-3-carbo-nitrile and 2-meth-oxy-4-(thio-phen-2-yl)-5,6,7,8,9,10-hexa-hydrocyclo-octa[<i>b</i>]pyridine-3-carbo-nitrile.

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Related Experiment Video

Updated: May 16, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Tricyclic flavonoids with 1,3-dithiolium substructure.

Lucian G Bahrin1, Peter G Jones, Henning Hopf

  • 1Department of Chemistry, "Al. I. Cuza" University of Iasi, 11 Carol I Bv., RO-700506 Iasi, Romania ; Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.

Beilstein Journal of Organic Chemistry
|December 5, 2012
PubMed
Summary
This summary is machine-generated.

New dithiocarbamic flavonoids were synthesized from 2-hydroxyaryl dithiocarbamates and aminals. Subsequent heterocyclization yielded novel tricyclic flavonoids with a fused 1,3-dithiolium-2-yl ring, offering new avenues in flavonoid chemistry.

Keywords:
aminalsbenzopyransdithiocarbamatesdithiolium saltsflavonoids

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Published on: September 8, 2013

Facile Preparation of 4-Substituted Quinazoline Derivatives
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Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Heterocyclic Chemistry

Background:

  • Flavonoids are a diverse class of natural products with significant biological activities.
  • The development of novel synthetic routes to functionalized flavonoids is crucial for exploring their therapeutic potential.
  • Dithiocarbamates are versatile synthetic intermediates in organic chemistry.

Purpose of the Study:

  • To synthesize novel 3-dithiocarbamic flavonoids.
  • To investigate the diastereoselectivity of the flavonoid synthesis.
  • To explore the heterocyclization of these flavonoids to form tricyclic systems.

Main Methods:

  • Reaction of 2-hydroxyaryl dithiocarbamates with aminals to form 3-dithiocarbamic flavonoids.
  • Separation and characterization of diastereoisomers.
  • Heterocyclization of the synthesized flavonoids.

Main Results:

  • Successful synthesis of new 3-dithiocarbamic flavonoids.
  • The synthesis predominantly yielded the anti diastereoisomer.
  • Novel tricyclic flavonoids featuring a 1,3-dithiolium-2-yl ring fused to the benzopyran moiety were obtained.

Conclusions:

  • The study presents a novel synthetic pathway to dithiocarbamic flavonoids.
  • The developed method allows for the formation of unique tricyclic flavonoid structures.
  • These findings expand the scope of flavonoid synthesis and may lead to compounds with new biological properties.