The Xanthate Route to Lactams

Samir Z Zard (1)

1 DCSO - Laboratoire de synthèse organique

Convergent routes to various classes of lactams exploiting the unique radical chemistry of xanthates are described. Emphasis is placed on reactions leading to lactams by direct radical cyclization, by intermolecular additions to alkenes followed by ring closure, and by radical additions to alkenes furnishing amino esters and aminoacids precursors that can be converted into lactams by ionic condensations. The possibility of modifying existing lactam structures is briefly discussed. Four-, five-, six-, seven-and, more rarely, eight-membered lactams can be constructed, including five-, six-, seven-membered lactams fused to aromatic and heteroaromatic rings. The latter are exemplified by oxindoles, azaoxindoles, tetrahydroquinolones, tetrahydroisoquinolones tetrahydroazaquinolones, tetrahydrobenazepinones, and tetrahydropyridoazepinones.

Mots clés: xanthates; radical addition; lactams; pyridones; radical Smiles

Domaines: Chimie organique

Samir Z Zard. The Xanthate Route to Lactams. Tetrahedron, 2021, 79, pp.131852. ⟨10.1016/j.tet.2020.131852⟩. ⟨hal-03416927⟩