European Journal of Chemistry

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

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Published: Sep 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.3.383-387.1029
Keywords:
Mentha, Artemisia, Lavandula, Terpenoids, Cycloaddition, Phenylnitrile oxide
Section
Research Article
Issue
Vol. 5 No. 3 (2014): September 2014
Dates
Received 2014-02-05
Accepted 2014-03-05
Published 2014-09-30


Main Article Content

Mohamed Rouani
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Bouchra Rahmouni
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Malika Chammache
Department of Chemistry, Heterocyclic Chemistry Laboratory, Faculty of Sciences, University Mohammed V Agdal, Rabat, BP1014, Morocco
Aziz El-Mebtoul
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco
Abdelkader Ilidrissi
Department of Chemistry, Laboratory of Plant Chemistry, Organic and Bio-organic Synthesis, Faculty of Sciences, University Mohammed V. Agdal, Rabat, BP1014, Morocco

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.


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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, 383-387.

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References

[1]. El-Mebtoul, A.; Rouani, M.; Chammache, M.; Bouidida, H.; Ilidrissi, A. Helvetica Chim. Acta 2011, 94, 433-437.
http://dx.doi.org/10.1002/hlca.201000246

[2]. Bouidida, H.; Alaoui, K.; Cherrah, Y.; Ilidrissi, A. Phytotherapie 2004, 4, 120-125.
http://dx.doi.org/10.1007/s10298-004-0035-0

[3]. Bouidida, H.; Alaoui, K.; Cherrah, Y.; Ilidrissi, A. S. F. P. T. Therapie 2006, 4, 1-6.

[4]. Talbaoui, A.; Jamaly, N.; Aneb, M.; Ilidrissi, A. J. Med. Plants Res. 2012, 6, 4593-4600.

[5]. Bouidida, H.; Alaoui, K.; Cherrah, Y.; Chammache, M.; Ilidrissi, A. Therapie 2008, 63, 333-338.
http://dx.doi.org/10.2515/therapie:2008048

[6]. Ghoulami, S.; Ilidrissi, A.; Bellakhdar, J. Fitoterapia 2001, 72, 596-598.
http://dx.doi.org/10.1016/S0367-326X(01)00279-9

[7]. Ghoulami, S.; Ilidrissi, A.; Bellakhdar, J. Tetrahedron Lett. 2001, 42, 2107-2109.
http://dx.doi.org/10.1016/S0040-4039(00)02355-8

[8]. Ilidrissi, A.; Maury, G.; Holeman, M.; Berrada, M. Fitoterapia 1990, 1, 23-29.

[9]. Oumzil, H.; Ghoulami, S.; Rhajaoui, M.; Ilidrissi, A.; Benjouad, A. Phytother. Res. 2002, 16, 727-731.
http://dx.doi.org/10.1002/ptr.1045

[10]. Amzazi, S.; Ghoulami, S.; Bakri, Y.; Ilidrissi, A.; Benjouad, A. S. F. P. T. Therapie 2003, 58, 531-534.
http://dx.doi.org/10.2515/therapie:2003086

[11]. Guenther, E. The essentiel oil, Ed. Van Nostrand Company NY, 1945.

[12]. Bellakhdar, J. La Pharmacopée Marocaine Traditionnelle, Ed. Ibis Press: Paris, 1997.

[13]. Ilidrissi, A.; Berrada, M.; Holeman, M. Planta Medica 1991, 57, 198-199.

[14]. Shiue, C. Y.; Lawler, R. G.; Clapp, L. B. J. Org. Chem. 1976, 12, 2210-2212.
http://dx.doi.org/10.1021/jo00874a031

[15]. Shiue, C. Y.; Park, K. P.; Clapp, L. B. J. Org. Chem. 1970, 35, 2065-2068.
http://dx.doi.org/10.1021/jo00831a095

[16]. Levy, G. C.; Nelson, G. L. J. Am. Chem. Soc. 1972, 94, 4897-4900.
http://dx.doi.org/10.1021/ja00769a017

[17]. Grundman, G.; Grunanger, P. Nitrile Oxides, Springer-Verlag New York, 1971.
http://dx.doi.org/10.1007/978-3-642-99991-8

[18]. Kambe, M.; Arai, E.; Suzuki, M.; Tokuyama, H. Org. Lett. 2001, 16, 2575-2578.
http://dx.doi.org/10.1021/ol016243t

[19]. Kadowaki, A.; Nagata, Y.; Uno, H.; Kamimura, A. Tetrahedron Lett. 2007, 48, 1823-1825.
http://dx.doi.org/10.1016/j.tetlet.2007.01.025

[20]. Hassaneen, H. M.; Shawali, A. H. Eur. J. Chem. 2013, 4(2), 102-109.
http://dx.doi.org/10.5155/eurjchem.4.2.102-109.723

[21]. Mandelli, D.; Steffen, R. A.; Shulpin, G. B. React. Kinet. Catal. Lett. 2006, 88, 165-173.
http://dx.doi.org/10.1007/s11144-006-0124-1

[22]. Bryliakov, K. P.; Talsi, E. P.; Stas'ko, S. N. J. Mol. Catal. 2003, 194, 79-88.
http://dx.doi.org/10.1016/S1381-1169(02)00527-7

[23]. Chandra, D.; Chandra, S. L.; Bhanmik, A. Appl. Catal. 2008, 342, 29-34.
http://dx.doi.org/10.1016/j.apcata.2007.12.041

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