Applications of Bartoli indole synthesis
Giuseppe Bartoli1, Renato Dalpozzo, Monica Nardi
1Dipartimento Chimica Industriale 'Toso Montanari', Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy. giuseppe.bartoli@unibo.it.
Chemical Society Reviews
|April 11, 2014
Summary
The Bartoli indole synthesis (BIS) offers a flexible and efficient method for creating 7-substituted indoles. This review highlights recent advancements in using BIS for complex indole preparations.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- The Bartoli reaction, discovered in 1989, involves the reaction of vinyl magnesium halides with ortho-substituted nitroarenes.
- It is a key method for synthesizing 7-substituted indoles, which are often challenging to prepare using classical indole syntheses.
- The Bartoli indole synthesis (BIS) has become a valuable tool in organic synthesis due to its efficiency and flexibility.
Purpose of the Study:
- To review the recent applications of the Bartoli indole synthesis in the preparation of complex indole derivatives.
- To highlight the versatility of the BIS, including its extension to heteroaromatic systems and solid-phase synthesis.
- To showcase the significance of BIS as a key step in modern synthetic strategies.
Main Methods:
- Literature review focusing on publications from the last few years.
- Analysis of synthetic routes employing the Bartoli indole synthesis.
- Examination of the scope and limitations of the BIS for complex molecule synthesis.
Main Results:
- The Bartoli indole synthesis is a versatile and efficient method for accessing 7-substituted indoles.
- Recent literature demonstrates the successful application of BIS in the synthesis of intricate indole structures.
- The reaction's adaptability extends to various substrates, including heteroaromatic nitro compounds and solid-supported synthesis.
Conclusions:
- The Bartoli indole synthesis remains a powerful and flexible method for indole construction.
- Recent advancements have expanded its utility in synthesizing complex and medicinally relevant indole compounds.
- The BIS is a crucial synthetic strategy for accessing challenging indole targets.
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