Details

Autor(en) / Beteiligte

• Ma, Jin-Tian
• Chen, Ting
• Chen, Xiang-Long
• Zhou, You
• Yu, Zhi-Cheng
• Zhuang, Shi-Yi
• Alimu, Maierhaba
• Wu, Yan-Dong
• Xiang, Jia-Chen
• Wu, An-Xin

Titel

One-step synthesis of azepino[3,4- b ]indoles by cooperative aza-[4 + 3] cycloaddition from readily available feedstocks

Ist Teil von

• Organic Chemistry Frontiers, 2022-08, Vol.9 (17), p.4640-4648

Ort / Verlag

London: Royal Society of Chemistry

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Azepino[3,4- b ]indoles are a family of molecules with pharmaceutical significance that contain an aza-seven-membered ring system. However, synthetic approaches to this scaffold are limited and typically require multiple steps. Here, we demonstrate the feasibility of obtaining azepino[3,4- b ]indoles by one-step synthesis from a four-component reaction system comprising readily available starting materials, i.e. , an amino acid, an indole, and an aniline. This transformation affords a diverse range of azepino[3,4- b ]indoles in a highly efficient manner. We propose that the self-sorting integration of two kinetically unstable intermediates, an indol-3-yl cation and an N -arylimine, is key to realizing the cooperative aza-[4 + 3] cycloaddition.