Issue 20, 2022

(3 + 2)-Annulation of 1,3-N,Si-tetraorganosilane reagents TsHNCH2SiBnR1R2 with arynes for efficient synthesis of 3-silaindolines

Abstract

1,3-N,Si-Tetraorganosilane reagents TsHNCH2SiBnR1R2 were developed as robust synthons to prepare 3-silaindolines via a Cs2CO3-promoted (3 + 2)-annulation reaction with arynes. The annulation involved a chemoselective Si–C bond cleavage/formation sequence, where the Si–Bn bond in TsHNCH2SiBnR1R2 and the Si–Ar bond in aryl silyl triflates were cleaved, and a new Si–Ar bond together with a N–Ar bond was formed. The nitrogen and aryl moieties in the products could be further functionalized to expand the structural diversity of 3-silaindolines. The approach allowed the development of a 3-silaindoline-containing CB2 agonist, which showed a higher CNS penetration and better antinociceptive effect than its carbon analog.

Graphical abstract: (3 + 2)-Annulation of 1,3-N,Si-tetraorganosilane reagents TsHNCH2SiBnR1R2 with arynes for efficient synthesis of 3-silaindolines

Supplementary files

Article information

Article type
Research Article
Submitted
05 jul 2022
Accepted
12 aug 2022
First published
18 aug 2022

Org. Chem. Front., 2022,9, 5453-5462

(3 + 2)-Annulation of 1,3-N,Si-tetraorganosilane reagents TsHNCH2SiBnR1R2 with arynes for efficient synthesis of 3-silaindolines

D. Cui, Y. Feng, Y. Gan, J. Yin, W. Wang, Y. Fan, L. Gao, B. Ke and Z. Song, Org. Chem. Front., 2022, 9, 5453 DOI: 10.1039/D2QO01075E

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