Vol. 4, Issue 9 (2015)
Search of Synthetic Approaches to 1, 3, 4-Oxadiazoles with 1, 2, 2-Trimethylcyclopentane Moiety
Ye O Tsapko
The work continues our research that deals with the search of biologically active compounds that are camphoric acid derivatives and dedicated to the synthesis of its new derivatives containing 1,3,4-oxadiazole cycle. To achieve this goal, at the first stage N'-aroylhydrazides of (±)-camphoric and (±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acids were synthesized by acylation of aromatic acids hydrazides. It was established that dehydration of the obtained hydrazides of (±)-camphoric acid ended up with closure of imide cycle and formation of N‑[(1S,5R),(1R,5S)-1,8,8-trimethyl-2,4-dioxo-3-azabicyclo[3.2.1]оct-3-yl]benzamides. The target 1,3,4-oxadiazoles with 1,2,2-trimethylcyclopentane moiety were managed to obtain from N'-aroylhydrazides of (±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acid.