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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

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.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Structure of Conjugated Dienes

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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(Z)-3-[(E)-3-Phenyl-allyl-idene]indolin-2-one.

Hongming Zhang¹, Shashidhar Kumar Akubathini, Haribabu Ankati

¹Department of Chemistry, Southern Methodist University, Dallas, TX 75275, USA.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

A novel compound C(17)H(13)NO was synthesized for neuroprotective activity testing. Its structure features indoline and phenyl-allyl-idene units linked by hydrogen bonds.

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Published on: July 17, 2020

Area of Science:

Medicinal Chemistry
Neuroscience
Crystallography

Background:

Neurodegenerative diseases pose significant health challenges.
Developing novel therapeutic agents is crucial for neuroprotection.
Understanding molecular structures aids in drug design.

Purpose of the Study:

To synthesize and characterize a new chemical entity, C(17)H(13)NO.
To evaluate the potential neuroprotective activities of the synthesized compound.
To elucidate the crystal structure and intermolecular interactions.

Main Methods:

Chemical synthesis of C(17)H(13)NO.
Single-crystal X-ray diffraction analysis.
Assessment of neuroprotective properties (details not provided in abstract).

Main Results:

The compound C(17)H(13)NO was successfully synthesized.
Crystal structure revealed an indoline and a phenyl-allyl-idene unit.
A dihedral angle of 9.0(1)° was observed between the ring systems.
Two independent molecules form dimers via intermolecular N-H⋯O hydrogen bonds.

Conclusions:

The synthesized compound C(17)H(13)NO possesses a defined molecular architecture.
The structural information provides a basis for understanding its potential biological activity.
Further studies are warranted to confirm its neuroprotective efficacy.