Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes

Abstract

The sulfonamide moiety was evaluated as an activating and stabilizing functional group in the metal templated strain release-driven intramolecular nucleophilic addition of amines to cyclopropenes to generate 1,5-diazocan-2-ones.

Construction of heterocyclic rings from cyclopropenes

“…This methodology is also suitable for the synthesis of diazobicycloalkanes such as 2,5-diazabicyclo[5.1.0]octan-6-ones by the cation-templated 7- and 8- exo-trig nucleophilic additions of amines across the CC bond of cyclopropene from Boc-protected amines tethered 3-cyclopropenecarboxylic acids. 47…”