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1,6-Stannatropic Strategy: Effective Generation and Cyclization of 1,5-Dipoles from o-Stannylmethylated Thioanilides or Phenyl Isothiocyanates

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journal contribution
posted on 17.08.2006, 00:00 by Satoshi Minakata, Yukihiro Kasano, Hirofumi Ota, Yoji Oderaotoshi, Mitsuo Komatsu
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.