A convergent route to substituted azetidines and to Boc-protected 4-aminomethylpyrroles

Songzhe Han (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

The radical addition of xanthates to Boc-protected azetine gives adducts, which can be reductively dexanthylated to furnish variously substituted azetidines. In the case of α-xanthyl ketones, treatment of the initial adducts with ammonia or primary amines, furnishes 2,4-disubstituted, 2,3,4-trisubstituted, and polycyclic pyrroles having a protected aminomethyl group at position-4. An unusual ring opening was observed in the case of a cyclobutanone precursor. It also proved possible to add an azetidinyl radical to an indole ring. Most of these products would be very difficult to obtain by more conventional routes.

Domains: Organic chemistry

Songzhe Han, Samir Z. Zard. A convergent route to substituted azetidines and to Boc-protected 4-aminomethylpyrroles. Tetrahedron, 2015, 71 (22), pp.3680-3689. ⟨10.1016/j.tet.2014.10.054⟩. ⟨hal-01178412⟩