Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles

Abstract

The conditions for the C-N bond forming reaction (C-N coupling reaction) between α-bromocarboxylate and nitrogen-containing non-aromatic heterocyclic rings under heterogeneous copper(I) oxide catalysis are investigated in this paper. All the generated compounds were fully characterized by IR, NMR and MS spectroscopy. Ab initio/DFT calculations of partial charges on nitrogen atoms in all the discussed heterocycles and on C(2) of carboxylate under applied conditions were predicted. These in silico results correlate relatively with the experimental observations.

Synthesis, physico-chemical properties and penetration activity of alkyl-6-(2,5-dioxopyrrolidin-1-yl)-2-(2-oxopyrrolidin-1-yl)hexanoates as potential transdermal penetration enhancers

“…Various conditions and yields of the C-N coupling of non-aromatic N-heterocycle starting materials were reported recently. 26 The series of seven target alkyl-6-(2,5-dioxopyrrolidin-1-yl)-2-(2-oxopyrrolidin-1-yl)hexanoates (4a-4g) was formed by conventional base-catalyzed transesterification 27 of the key intermediate 3 in excess of corresponding primary unbranched alcohol. The discussed compounds were synthesized according to Scheme 1.…”