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Related Concept Videos

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
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A reduction-oxidation reaction is commonly called a redox reaction. In a redox reaction, electrons are transferred from one species to another rather than being shared between or among atoms. The reducing agent or reductant is the species that loses electrons and gets oxidized in the process. The species that gains electrons and gets reduced in the process is the oxidizing agent or oxidant. Redox reactions are represented as two separate equations called half-reactions, where one equation...
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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...

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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

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Redox-neutral indole annulation cascades.

Michael C Haibach1, Indubhusan Deb, Chandra Kanta De

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.

Journal of the American Chemical Society
|February 2, 2011
PubMed
Summary
This summary is machine-generated.

Aminobenzaldehydes and indoles undergo a novel cascade reaction, forming polycyclic azepinoindoles. This acid-catalyzed process involves condensation, hydride shift, and ring closure in one step.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Published on: June 20, 2014

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Indole derivatives are prevalent in pharmaceuticals and natural products.
  • Efficient synthesis of complex polycyclic scaffolds remains a challenge.

Purpose of the Study:

  • To develop a novel, efficient synthetic route to polycyclic azepinoindoles.
  • To explore a new cascade reaction involving aminobenzaldehydes and indoles.

Main Methods:

  • Acid-catalyzed reaction of substituted aminobenzaldehydes with various indoles.
  • Characterization of reaction products using NMR spectroscopy, mass spectrometry, and X-ray crystallography.

Main Results:

  • An unprecedented cascade reaction between aminobenzaldehydes and indoles was discovered.
  • The reaction proceeds via a condensation/1,5-hydride shift/ring-closure mechanism.
  • Polycyclic azepinoindoles were synthesized in good to excellent yields in a single step.

Conclusions:

  • A novel and efficient one-step synthesis for polycyclic azepinoindoles has been established.
  • The developed cascade reaction offers a valuable tool for accessing complex indole-containing heterocycles.
  • This methodology holds potential for the synthesis of novel pharmaceutical agents.