Bartoli indole synthesis

What is Bartoli indole synthesis?

In 1989, Giuseppe Bartoli first reported a reaction known as the Bartoli indole synthesis, which involves treating ortho-substituted nitroarenes with vinylmagnesium bromide to produce 7-substituted indole, after aqueous work up of the mixture.

Bartoli indole synthesis
Bartoli indole synthesis

This approach has become the most efficient and adaptable method for synthesizing indoles with 7-substituents. Bartoli’s earlier research on the reaction between nitroarenes and Grignard reagents led to the development of this reaction. He discovered that vinylmagnesium bromide and nitroarenes can create aromatic nitroso compounds.

In addition to its general use in creating 7-substituted indoles, the Bartoli indole synthesis has other applications, such as the synthesis of azaindoles and optically pure 7-alkoxyltryptophan.

References

Giuseppe Bartoli, Gianni Palmieri, Marcella Bosco, Renato Dalpozzo,
The reaction of vinyl grignard reagents with 2-substituted nitroarenes: A new approach to the synthesis of 7-substituted indoles,Tetrahedron Letters 30 (16) 2129-2132 (1989)
DOI: 10.1016/S0040-4039(01)93730-X

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