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Indole synthesis - Organic Chemistry Portal

Craig
1975, Nair’s paper provides a proof of concept




No further work was published
This project was aimed at an optimisation of the reaction of 2H-azirines and arynes to make indole derivatives

Can other heterocycles be formed with this method?



Summary
Indoles
Proposed mechanism
Optimisation of the reaction
The synthesis of azirines
Changing of the azirine
The synthesis of aryne precursors
Changing the aryne precursor
The synthesis of other heterocycles
Conclusion
The Fischer indole synthesis:

Harsh conditions needed, strong bases or acids, and heat
The proposed mechanism
Azirines - an alternative synthesis?

Scalable Total Syntheses of (−)-Hapalindole U and (+)-Ambiguine H, Tetrahedron 2015, 71, 3652–3665

Bartoli indole synthesis - Wikipedia


Method 1.
Method 2.
Scope - Changing the 2H-azirine
para-
effect - EWG
Order of reactivity
Replacing the arene by an alkyl chain
Carbocation intermediate in the mechanism
Order of bond formation
Electron rich azirines are difficult to synthesise
Azirines are less reactive than furanes towards arynes

Other heterocycles
New mechanism?
Strained cumulene hypothesis
Scope - changing the aryne precursor
Aryne precursor synthesis
Azirines and arynes can yield indole derivatives in mild conditions
A model reaction was optimised and examples were synthesised






Future work involves :
- Determining the mechanism
- Expanding scope
- Expanding the other heteroatoms idea

Quinolines?
Indolines?

As an extension of our syntheses of fused heterocycles using lithiation methods, we have pursued the synthesis of novel 3,3'-diiodo-2,2'-biindoles, oxazolylindoles, bis(3-indolylacetylene), bisindolylmaleimides, and indolocarbazoles.

Fischer Indole Synthesis - Organic Chemistry Portal

A few studies demonstrate the beneficial effects of indole-3-carbinol on lipid synthesis and platelet aggregation, suggesting that this phytochemical could help to .
I3C, 3-hydroxymethyl indole, 3-indole methanol


In our study of the fused heterocycles pyrrolo[3,4-b]indoles and pyrrolo[2,3-b]indoles, we have uncovered a novel ipso acylation�detosylation reaction upon reaction with acid chlorides and aluminum chloride leading to the corresponding acylated heterocycles.

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Synthesis of 3-Substituted Indoles - TCI Chemicals


Synthesis of 3-Substituted Indoles,Synthesis of 3-Substituted Indoles

For example, as a route to the trikentrin and herbindole group of biologically active natural products, we have carried out an intramolecular Diels-Alder cycloaddition of the fused heterocycle furo[3,4-b]pyrrole to afford a tricyclic indole embodying the structure of these natural indoles.

A Simple Synthesis of 2-Substituted Indoles

Gribble, Dartmouth CollegeThe present project involves the synthesis and exploitation of fused heterocycles as vehicles for the synthesis of biologically important indoles, carbazoles, carbolines, and other natural products.

Studies Towards the synthesis of indoles using arynes …

Direct Coupling of Indoles with Carbonyl Compounds: Short, Enantioselective, Gram-Scale Synthetic Entry into the Hapalindole and Fischerindole Alkaloid Families, J.

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