Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles

Conversion of Cyclic Ketones to 2,3-Fused Pyrroles and Substituted Indoles

A highly effective synthesis of 2,3-fused pyrroles from cyclic ketones has been achieved. The transformation includes a rhodium-catalyzed reaction of 4-alkenyl-1-sulfonyl-1,2,3-triazoles featuring an unusual 4π electrocyclization. The methodology was further extended to the synthesis of indoles usin...

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Veröffentlicht in:Journal of the American Chemical Society 2013-08, Vol.135 (32), p.11712-11715
Hauptverfasser: Alford, Joshua S, Spangler, Jillian E, Davies, Huw M. L
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Ketones - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Rhodium - chemistry
Triazoles - chemistry
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Zusammenfassung:A highly effective synthesis of 2,3-fused pyrroles from cyclic ketones has been achieved. The transformation includes a rhodium-catalyzed reaction of 4-alkenyl-1-sulfonyl-1,2,3-triazoles featuring an unusual 4π electrocyclization. The methodology was further extended to the synthesis of indoles using a one-pot reaction starting from 1-ethynylcyclohexenes.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja405043g