Synthesis of Fused Heterocycles via Cascade 1,2-Silyl Shift – Friedel–Crafts Cyclization

Balticum Organicum Syntheticum 2024: Program and Abstract Book 2024
Artjoms Ubaidullajevs, Rasma Kroņkalne, Krišjānis Gercāns, Māris Turks

Herein we report a new synthetic pathway to fused heterocycles. The key synthetic step involves tandem 1,2-silyl shift – Friedel–Crafts cyclization. First, propargyl silane 1 undergoes an electrophilic attack, which induces silyl group migration in an anti-fashion. This provides a relatively stable allylic cation 2, which can further react with the internal nucleophile. Previously, our scientific group successfully applied this concept by affording 5-membered carbocycles1 or heterocycles2. In this work, we expand our method to the synthesis of 6-membered heterocycles 3.

Atslēgas vārdi
1,2-Silyl Shift, Friedel–Crafts Cyclization, Fused Heterocycles, Propargyl Silanes

Ubaidullajevs, A., Kroņkalne, R., Gercāns, K., Turks, M. Synthesis of Fused Heterocycles via Cascade 1,2-Silyl Shift – Friedel–Crafts Cyclization. No: Balticum Organicum Syntheticum 2024: Program and Abstract Book, Latvija, Riga, 7.-10. jūlijs, 2024. Riga: 2024, 157.-157.lpp.

Publikācijas valoda
English (en)