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

[ Vol. 15 , Issue. 12 ]

Author(s):

Guilhem Chaubet, Mathéo Berthet, Morgane Pasco, Guillaume Cazals, Aurélien Lebrun, Jean Martinez and Isabelle Parrot *   Pages 1046 - 1055 ( 10 )

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.

Keywords:

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

Affiliation:

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

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