1,6-Stannatropic strategy: effective generation and cyclization of 1,5-dipoles from o-stannylmethylated thioanilides or phenyl isothiocyanates.
[reaction: see text] A new method for the generation of 1,5-dipoles from o-stannylmethylated thioanilides via 1,6-stannatropy under neutral conditions was developed. Cyclization of the 1,5-dipoles afforded indole derivatives effectively. The strategy has potential for application to the generation of alternative 1,5-dipoles from o-stannylmethylated aryl isothiocyanates leading to indole derivatives having a stannylthio group that was readily converted to other functional groups.
Minakata
Satoshi
S
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan. minakata@chem.eng.osaka-u.ac.jp
Kasano
Yukihiro
Y
Ota
Hirofumi
H
Oderaotoshi
Yoji
Y
Komatsu
Mitsuo
M