2013 · JOURNAL OF ORGANIC CHEMISTRY

A Sonogashira Cross-Coupling/5-exo-dig Cyclization/Ionic Hydrogenation Sequence: Synthesis of 4-Substituted 3-Azabicyclo[3.1.0]hexan-2-ones from 2-Iodocyclopropanecarboxamides

de Carne-Carnavalet, Benoit, Meyer, Christophe, Cossy, Janine, Folleas, Benoit, Brayer, Jean-Louis, Demoute, Jean-Pierre

Journal
JOURNAL OF ORGANIC CHEMISTRY
Année
2013
Volume
78
Numéro
11
Pages
5794-5799
Mois
JUN 7
DOI
10.1021/jo400713u

Abstract

A variety of 4-substituted 3-azabicyclo[3.1.0]hexan-2-ones have been prepared from 2-iodocyclopropane-carboxamides by a three-step sequence involving a copper-free Sonogashira coupling with terminal aryl- or heteroarylalkynes, followed by a 5-exo-dig cyclization and an ionic hydrogenation.

Lire l'article complet