On the Reactivity of (−)‐(R)‐Carvone and (−)‐4aα,7α,7aβ‐Nepetalactone: Synthesis of New Heterocycles |
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| Authors: | Aziz El Mebtoul Mohamed Rouani Malika Chammache Houcine Bouidida Abdelkader Ilidrissi |
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| Affiliation: | 1. Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio‐organic Synthesis, University Mohammed V Agdal, Faculty of Sciences, Rabat, Morocco;2. Department of Chemistry, Heterocyclic Chemistry Laboratory, University Mohammed V Agdal, Faculty of Sciences, Rabat, Morocco, (phone: +212 0668547336;3. fax: +212 0537775440);4. Present address: Abdelkader Ilidrissi, Residence Mesk Ellil, Immeuble 9, N°?3, Hay Ryad 10110, Rabat, Maroc. |
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| 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 NH2OH to yield a new heterocycle, observed for the first time. On the other hand, the addition of 4‐chlorobenzonitrile oxide to the unsaturated lactone (?)‐4aα,7α,7aβ‐nepetalactone gave, in a good yield, also a new heterocycle, again obtained for the first time. The terpenoid (?)‐(R)‐carvone and iridoid (?)‐4aα,7α,7aβ‐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. |
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| Keywords: | (− )‐(R)‐Carvone Nepetalactone Nepeta tuberosa Mentha viridis Phenylnitrile oxide, 4‐chloro‐ Cycloadditions |
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