A simple and efficient synthetic procedure for the preparation of indole-, 7-azaindole-, and pyrrol-containing tertiary alcohols from indole/azaindole/pyrrole and TEMPO-substituted 1,3-dicarbonyl compounds were developed. The mechanistic pathway for this process involves the N-O bond cleavage of TEMPO-substituted 1,3-dicarbonyl compounds to form the tricarbonyl intermediate, following Friedel-Crafts reaction of indole/aza-indole/pyrrole with this intermediate generates the tertiary alcohol product. All the processes do not need extra catalysts, dry solvents or harsh reaction conditions.
Fangfang Zhuang, Jianwei Yan, Fulin Yan and Ke Cao
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