European Journal of Chemistry 2014, 5(3), 383-387 | doi: https://doi.org/10.5155/eurjchem.5.3.383-387.1029 | Get rights and content






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Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles


Mohamed Rouani (1) , Bouchra Rahmouni (2) , Malika Chammache (3) , Aziz El-Mebtoul (4) , Abdelkader Ilidrissi (5,*)

(1) Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
(2) Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
(3) Department of Chemistry, Heterocyclic Chemistry Laboratory, Faculty of Sciences, University Mohammed V Agdal, Rabat, BP1014, Morocco
(4) Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
(5) Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
(*) Corresponding Author

Received: 05 Feb 2014 | Accepted: 17 Mar 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


Reactivity comparison by 1,3-dipolar cycloaddition of the three dipolarophiles (-)-R-Carvone (I), (-)-R-Linalool (II) and derivative of (-)-(1S,4S)-camphor (III) has been studied. By reactions of p-chlorophenylnitrile oxide, new heterocycles are obtained by stereospecific reactions for cyclic Terpenoids I and III (regardless of the length of the side chain). However the aliphatic dipolarophile II gives two diastereoisomers. Terpenoids (-)-R-Carvone I (-)-R-Linalool II and (-)-(1S,4S)-Camphor 1 are isolated respectively from Moroccan species Mentha viridis (L.), Lavandula officinalis (L.) and Artemisia herba halba (Asso). The new heterocycles obtained were identified by combination of chromatographic and spectroscopic methods.


Keywords


Mentha; Artemisia; Lavandula; Terpenoids; Cycloaddition; Phenylnitrile oxide

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DOI: 10.5155/eurjchem.5.3.383-387.1029

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Funding information


CNRST-UATRS "URAC 23".

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How to cite


Rouani, M.; Rahmouni, B.; Chammache, M.; El-Mebtoul, A.; Ilidrissi, A. Eur. J. Chem. 2014, 5(3), 383-387. doi:10.5155/eurjchem.5.3.383-387.1029
Rouani, M.; Rahmouni, B.; Chammache, M.; El-Mebtoul, A.; Ilidrissi, A. Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles. Eur. J. Chem. 2014, 5(3), 383-387. doi:10.5155/eurjchem.5.3.383-387.1029
Rouani, M., Rahmouni, B., Chammache, M., El-Mebtoul, A., & Ilidrissi, A. (2014). Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles. European Journal of Chemistry, 5(3), 383-387. doi:10.5155/eurjchem.5.3.383-387.1029
Rouani, Mohamed, Bouchra Rahmouni, Malika Chammache, Aziz El-Mebtoul, & Abdelkader Ilidrissi. "Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles." European Journal of Chemistry [Online], 5.3 (2014): 383-387. Web. 11 Aug. 2020
Rouani, Mohamed, Rahmouni, Bouchra, Chammache, Malika, El-Mebtoul, Aziz, AND Ilidrissi, Abdelkader. "Comparative study of reactivity of (-)-R-carvone, (-)-R-linalool and (-)-(1S,4S)-camphor derivatives: Synthesis of new heterocycles" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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DOI Link: https://doi.org/10.5155/eurjchem.5.3.383-387.1029

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