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Fused Bis-lactams to Spirolactams: A New Member of the Family of Ring- Contraction Reaction

2018; Bentham Science Publishers; Volume: 15; Issue: 12 Linguagem: Inglês

10.2174/1570178615666180326160131

1875-6255

Guilhem Chaubet, Mathéo Berthet, Morgane Pasco, Guillaume Cazals, Aurélien Lebrun, Jean Martínez, Isabelle Parrot,

Asymmetric Synthesis and Catalysis

A new ring contraction of fused bis-lactams into spirolactams is presented here. In the presence of a triflate catalyst in various solvents under microwave irradiation, this rearrangement allows a clean conversion of some fused bicycles into spirocycles with good yields. The interest of this work thus lies in the use of activated 2,5-diketopiperazines as starting materials and demonstrates the wide range of applications of ring contraction reactions. Keywords: Spirolactams, ring-contraction, heterocycles, homologous, cyclic compound, pyrrole.