Indole synthesis from N-allenyl-2-iodoanilines under mild conditions mediated by samarium(II) diiodide

A novel method for indole skeleton synthesis under mild conditions mediated by samarium(ii) diiodide has been developed. The reaction of N-allenyl-2-iodoaniline derivatives with SmI2 in the presence of HMPA and i-PrOH at 0 °C afforded indole derivatives in high yields.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-09, Vol.12 (35), p.6812-6815
Main Authors: Iwasaki, Hiroki, Suzuki, Kenji, Yamane, Mitsunari, Yoshida, Shohei, Kojima, Naoto, Ozeki, Minoru, Yamashita, Masayuki
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Chemistry, Organic - methods
Cyclization
Electrons
Hempa - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Iodides - chemistry
Models, Chemical
Molecular Structure
Samarium - chemistry
Temperature
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Summary:A novel method for indole skeleton synthesis under mild conditions mediated by samarium(ii) diiodide has been developed. The reaction of N-allenyl-2-iodoaniline derivatives with SmI2 in the presence of HMPA and i-PrOH at 0 °C afforded indole derivatives in high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01164c