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 Indole moiety is the most abundant heterocycle in nature.

Biosynthesis of Tryptophan

 

Roadmap of Indole Synthesis

 

Detailed Name Reaction Example

Fisher Indole Synthesis. Different acid could be used in this synthesis, HCl, TFA, AcOH, and even Lewis acids.       

Org. Prep. Proced. Int. 2002, 34 (5), 507. also J. Heterocycle Chem. 2002, 39 (2), 315

Borsche-Drechsel cyclization
Bartoil Indole Synthesis. The mechanism (reductive what?) is not fully understood for me.   

Synth. Commun. 1991, 21,  611;  Tetrahedron Lett. 1989, 30 (16), 2129-2132

Nucleophilic substitution, reduction and  cyclization.  

Org. Prep. Proced. Int. 2002, 34 (5), 483

Nenitzescu Indole synthesis. Reductive cyclization.  

Org. Prep. Proced. Int 2002, 34 (5), 483

Bischler Indole sythesis.  
Allylation and coupling.       

J. Org. Chem. 1991, 56 (9), 3048.

Madelung indole synthesis.       
        

 

        

 

        

 

        

 

Drug Synthesis Example

Benzofuran and Benzothiophene


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