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Paper | Special issue | Vol 99, No. 1, 2019, pp.465-483
Published online, 21st November, 2018
DOI: 10.3987/COM-18-S(F)42
A [3,3] Sigmatropic and Novel Ipso [3,3] Sigmatropic Rearrangement of 1-Hydroxyindole Chemistry

Yoshikazu Fukui, Tetsuya Kobayashi, Toshiya Kawasaki, Fumio Yamada, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan


Utilizing 1-aryloxyindole derivatives, we found a new type of [3,3] sigmatropic rearrangement reaction. We named it as ipso [3,3] sigmatropic rearrangement. The product structures are strictly determined by X-ray crystallographic analysis. Normal [3,3] sigmatropic rearrangement of 1-hydroxyindole derivative was found to be a useful synthetic method for 2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione derivative.