Gallium/Indium-Promoted [4 + 2] Annulation of 2‑Aminobenzonitriles with Alkynes and Dimerization of 2‑Aminobenzonitriles: One-Pot Access to 4‑Aminoquinolines and 4‑Amino-2-Arylquinazolines
Norio Sakai, Mio Ishii, Shuji Yamauchi, Yohei Ogiwara, Kento Ishida · 2026
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Description
Norio Sakai and co-authors reported in 2026 a one-pot route to two families of nitrogen ring compounds valued in drug research. Aminoquinolines appear in antimalarial and antitumor agents, yet joining them with plain alkynes had proved stubborn. Their team used gallium or indium salts, group thirteen Lewis acids, to drive the ring-forming reaction.
With these promoters, 2-aminobenzonitriles combined with many terminal and internal alkynes to give 4-aminoquinolines in moderate to good yields. Halogen, ester, and silicon-bearing partners all survived the conditions. Switching to gallium chloride alone pushed a different path: two molecules of the starting nitrile paired up instead. That dimerization delivered 4-amino-2-arylquinazolines in good yield. The authors present both reactions as practical entries into scaffolds that medicinal chemists reuse often.
Catalog record
| CREATOR | Norio Sakai, Mio Ishii, Shuji Yamauchi, Yohei Ogiwara, Kento Ishida |
|---|---|
| YEAR | 2026 |
| COLLECTION | PAPERS |
| FORMAT | TXT |
| FILE SIZE | 46 KB |
| VERSION | 1.0 |
| LICENSE | CC BY 4.0 |
| RIGHTS | CC BY |
| SOURCE | Europe PMC |