Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 1, Pages 460-472Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo202012n
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Funding
- Agencia Cordoba Ciencia
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET)
- SECYT
- Universidad Nacional de Cordoba
- FONCYT, Argentina
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A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular a-aryl ketone bond by the photostimulated S(RN)1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular C-Ar-C-Ar coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed.
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