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Preparation of Amides01:29

Preparation of Amides

3.0K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.4K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.4K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.1K
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).
2.1K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K

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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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Indole-2-carboxamide: a versatile synthetic handle for the synthesis of diversely substituted polycyclic indole

Akshay Kamble1, Priyanka Deore2, Vanshika Agrawal2

  • 1Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Ahmedabad (NIPER-A), Gandhinagar, Gujarat - 382355, India.

Organic & Biomolecular Chemistry
|June 12, 2025
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Summary
This summary is machine-generated.

This review details the synthesis of polycyclic fused indoles using indole-2-carboxamide. It highlights advancements and mechanisms for creating these important N-heterocyclic scaffolds.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Heterocyclic Chemistry

Background:

  • Indoles are crucial N-heterocycles in natural products, exhibiting diverse biological activities.
  • Many bioactive indoles feature complex polycyclic frameworks, necessitating efficient synthetic strategies.
  • Indole derivatives serve as versatile precursors for constructing these essential polycyclic scaffolds.

Purpose of the Study:

  • To review synthetic advancements in constructing polycyclic fused indole molecules.
  • To highlight indole-2-carboxamide as a key precursor in these syntheses.
  • To discuss the synthetic potential and reaction mechanisms involved.

Main Methods:

  • Focuses on cyclization reactions (intramolecular and intermolecular) utilizing indole-2-carboxamide.
  • Summarizes established and emerging synthetic methodologies.
  • Includes mechanistic insights into fused polycyclic indole formation.

Main Results:

  • Demonstrates the utility of indole-2-carboxamide for accessing various fused indole ring systems.
  • Provides a comprehensive overview of synthetic routes to polycyclic indoles.
  • Elucidates reaction pathways for constructing these complex molecules.

Conclusions:

  • Indole-2-carboxamide is an essential precursor for synthesizing polycyclic fused indoles.
  • Significant progress has been made in developing synthetic strategies for these compounds.
  • Further exploration of this scaffold holds promise for discovering new bioactive molecules.