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Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...

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Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

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Heterocycles from cyclopropenones.

Ashraf A Aly¹, Alaa A Hassan¹, Sara M Mostafa¹

¹Chemistry Department, Faculty of Science, Minia University El-Minia 61519 Egypt ashrafaly63@yahoo.com ashraf.shehata@mu.edu.eg alaahassan2001@mu.edu.eg sara.ahmed@mu.edu.eg esraamah33@gmail.com asmaa.hamouda@mu.edu.eg.

|July 25, 2022

Summary

Cyclopropenones, found in nature and synthesized, are versatile organic compounds. This review highlights their novel utility in synthesizing diverse heterocyclic compounds, a significant area in organic chemistry.

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Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Cyclopropenones are naturally occurring and synthesized compounds with diverse biological activities.
These derivatives participate in numerous chemical reactions, including ring-opening, C-C coupling, and cycloaddition.

Purpose of the Study:

To provide a comprehensive review of cyclopropenone utility in heterocyclic synthesis.
To highlight a previously unreported application of cyclopropenones in organic synthesis.

Main Methods:

Compilation of synthetic methods utilizing cyclopropenones.
Review of literature focusing on cyclopropenone-mediated heterocycle formation.

Main Results:

Demonstration of cyclopropenones as valuable synthons for various heterocyclic ring systems.
Identification of novel synthetic pathways enabled by cyclopropenone chemistry.

Conclusions:

Cyclopropenones offer a unique and efficient route to diverse heterocyclic structures.
This review establishes a new direction for cyclopropenone chemistry research and application.