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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.0K
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
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.5K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.8K
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
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.7K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.7K

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Related Experiment Video

Updated: May 23, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Modular Approach for Photoinduced Cycloaddition Enabling the Synthesis of Diverse Bioactive Oxazoles.

Argha Saha1, Emanuele Casali2, Ankan Ghosh3

  • 1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

Organic Letters
|March 10, 2025
PubMed
Summary

This study introduces a metal-free, light-driven reaction for synthesizing bioactive oxazoles efficiently. The method simplifies the creation of complex oxazole derivatives, natural products, and pharmaceuticals.

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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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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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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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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Traditional synthesis of bioactive oxazoles faces challenges with efficiency and complex derivatives.
  • Existing methods are often limited in scope and application for intricate molecular structures.

Purpose of the Study:

  • To develop a novel, efficient, and economical method for synthesizing bioactive oxazoles.
  • To explore the application of this new method for creating complex natural products and pharmaceuticals.

Main Methods:

  • Utilized a metal-free, photomediated [3 + 2] cycloaddition reaction.
  • Employed readily available diazo compounds and nitriles as starting materials.

Main Results:

  • Achieved a step- and reagent-economical synthesis of diverse bioactive oxazoles.
  • Successfully synthesized natural products (annuloline, pimprinethine, labradorin 2) and pharmaceuticals (oxaprozin).
  • Demonstrated the synthesis of deuterium-labeled and heterocyclic-based oxazoles.

Conclusions:

  • The developed photomediated cycloaddition offers a versatile and efficient route to valuable oxazole compounds.
  • This method expands synthetic possibilities for medicinal chemistry and natural product synthesis.