A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes

[Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the...

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Detalles Bibliográficos
Autores principales: Markey, Sophie J., Lewis, William, Moody, Christopher J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971735/
https://www.ncbi.nlm.nih.gov/pubmed/24280001
http://dx.doi.org/10.1021/ol403191k
Descripción
Sumario:[Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the Boc-group, and 6π-electrocyclization to α-carbolines, following aromatization by loss of methanol (11 examples, 30–90% yield).

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