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On the Reactivity of (−)‐( R )‐Carvone and (−)‐4a α ,7 α ,7a β ‐Nepetalactone: Synthesis of New Heterocycles
Author(s) -
El Mebtoul Aziz,
Rouani Mohamed,
Chammache Malika,
Bouidida Houcine,
Ilidrissi Abdelkader
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000246
Subject(s) - chemistry , carvone , yield (engineering) , derivative (finance) , stereochemistry , cycloaddition , terpenoid , monoterpene , reactivity (psychology) , terpene , organic chemistry , limonene , essential oil , catalysis , alternative medicine , medicine , materials science , chromatography , pathology , financial economics , economics , metallurgy
Abstract The 1,3‐dipolar cycloaddition of 4‐chlorobenzonitrile oxide to the unsaturated system of (−)‐( R )‐carvone occurred exclusively at C(8) to give a new isoxazoline derivative. This derivative reacts with NH 2 OH to yield a new heterocycle, observed for the first time. On the other hand, the addition of 4‐chlorobenzonitrile oxide to the unsaturated lactone (−)‐4a α ,7 α ,7a β ‐nepetalactone gave, in a good yield, also a new heterocycle, again obtained for the first time. The terpenoid (−)‐( R )‐carvone and iridoid (−)‐4a α ,7 α ,7a β ‐nepetalactone were isolated from Moroccan species Mentha viridis (L.) and Nepeta tuberosa (L.), respectively . The new heterocycles obtained were identified by combination of chromatographic and spectroscopic methods.