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

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

Volume: 15 Issue: 12

Author(s): Guilhem Chaubet, Mathéo Berthet, Morgane Pasco, Guillaume Cazals, Aurélien Lebrun, Jean Martinez and Isabelle Parrot *

Affiliation:

• Institut des Biomolecules Max Mousseron, IBMM UMR-5247 CNRS, Universite de Montpellier, ENSCM, CC 17-03, Pl. E. Bataillon, 34095 Montpellier, Cedex 5,France

Keywords: Spirolactams, ring-contraction, heterocycles, homologous, cyclic compound, pyrrole.

Abstract: 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.

Cite this article as:

Chaubet Guilhem , Berthet Mathéo , Pasco Morgane , Cazals Guillaume , Lebrun Aurélien , Martinez Jean and Parrot Isabelle *, Fused Bis-lactams to Spirolactams: A New Member of the Family of Ring- Contraction Reaction, Letters in Organic Chemistry 2018; 15 (12) . https://dx.doi.org/10.2174/1570178615666180326160131