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Cascades to substituted indoles.

J D Rainier¹, A R Kennedy

¹Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA. rainer@u.arizona.edu

The Journal of Organic Chemistry

|September 16, 2000

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This study introduces a novel method for synthesizing dithioindoles using free-radical cyclizations. These dithioindoles are then used to create substituted and spiro-fused indoles.

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Indole derivatives are prevalent in pharmaceuticals and natural products.
Efficient synthetic routes to functionalized indoles are highly sought after.

Purpose of the Study:

To develop a novel synthetic pathway for dithioindoles.
To explore the utility of dithioindoles in synthesizing substituted and spiro-fused indoles.

Main Methods:

Free-radical cyclization of arylisonitriles with pendant alkynes to form dithioindoles.
Coupling of dithioindoles with active hydrogen-containing compounds.

Main Results:

Successful synthesis of dithioindoles via free-radical cyclization.
Demonstrated synthesis of diverse substituted and spiro-fused indoles from dithioindoles.

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Conclusions:

The described method provides an efficient route to dithioindoles.
Dithioindoles serve as versatile intermediates for indole synthesis.