RESEARCH ARTICLE


A New Synthetic Method of 1,5-Dimethyl-3-Oxabicyclo[3.1.0] Hexane-2,4-Dione



Youcef Mechehoud1, Nadjah Belattar1, *, Samir Benayache1, Fadila Benayache1, Paul Mosset2
1 Research Unity of Valorization of Natural Resources, Bioactive Molecules and Physicochemical Biological Analysis, Department of Chemistry, Faculty of Exact Sciences, University of Mentouri- Brothers, Constantine-1, 25000, Algeria.
2 University of Rennes, 1263 Avenue of General Leclerc, Building 10 A, Door 154/1, 35042 Rennes Cedex, France


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© 2018 Mechehoud et al.

open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

* Address correspondence to this author at the Research Unity of Valorization of Natural Resources, Bioactive Molecules and Physicochemical Biological Analysis, Department of Chemistry, Faculty of Exact Sciences, University of Mentouri- Brothers, Constantine-1, Algeria; E-mail: nadjahorg@gmail.com


Abstract

Background:

We have described in this reported work a new method in the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione in good yield.

Objective:

Optimization of practical conditions leads to obtain 1,3-cyclopropanedicarboxylic anhydrides as important precursors of functionalized cyclopropane derivatives.

Method:

The condensation of 2-chloropropanoic acid with ethyl methacrylate using (2M) LDA dissolved in hexane and THF at (-80°C), and the treatment with acetyl chloride permit to obtain the substituted 1,3- cyclopropanedicarboxylic anhydride .

Results:

We have proceeded to the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione as functionalized organic compound with high efficiency ,taking into account the regioselectivity of carbanion attack to double bond activated by an electrophilic group.

Conclusion:

Using (2M) LDA dissolved in hexane and THF at (-80°C) is a good way to afford the enantioselective substituted 1,3- cyclopropanedicarboxylic anhydrides.

Keywords: Cis-3-oxabicyclo, LDA, Cyclopropanedicarboxylic anhydrides, Condensation, Regioselectivity, Electrophilic.