Журнал "Макрогетероциклы"

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054 Ufa, Russia

^@Corresponding author E-mail: insect@anrb.ru

 

DOI: 10.6060/mhc190660y

Macroheterocycles 2020 13(1) 74-78

 

Based on the available natural monoterpene ∆³-carene we have developed the synthesis of four optically pure macroheterocycles with ester and dihydrazide fragments through the intermediate 1-((1S,3R)-3-(2-hydroxyethyl-2,2-dimethylcyclopropyl)propan-2-one using its [2+1]-interaction with dichloranhydrides of adipic or 2,6-pyridinedicarboxylic acids and [1+1]-condensation of the obtained α,ω-diketodiesters with dihydrazides of adipic or 2,6-pyridinedicarboxylic acids. The structure of new compounds was confirmed by IR and NMR spectroscopy and mass spectrometry.