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ISSN 1998-9539

Synthesis of Optically Pure Macroheterocycles with 2,6-Pyridinedicarboxylic and Adipic Acid Fragments from ∆3-Carene

Marina P. Yakovleva,@ Kseniya S. Denisova, Galina R. Mingaleeva, Valentina A. Vydrina, and Gumer Yu. Ishmuratov
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.
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