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

@inproceedings{Markey2013ANR,
  title={A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes},
  author={Sophie J. Markey and William Lewis and Christopher J Moody},
  booktitle={Organic letters},
  year={2013}
}
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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