Preparation of Polyfunctioneled 1,2-Benzylated Derivatives from O-Salycilique Aldehyde and B-Ketoesters

Regadia Aissaoui , Ahmed Khalifa , Zineb Mokhtari , Aissa Benhamida , Khamiss Kussay , Noureddine Gherraf


1, 2 Polyfunctionalized benzene derivatives have been important structural units present in certain molecules used in a wide range of applications (pharmaceutical, biological, cosmetic, etc.). In this work, the synthesis of 1 and 2 polyfunctionalized benzene derivatives has been proceeded from largely available and cheap reagents namely: β-keto-ester salicylic aldehydes and alkyl halides. The inspiring obtained results emphasized on the interesting strategy implemented for the synthesis of such molecules. The NMR spectroscopic analysis was used to identify the structure of different isolated products in the form of a single stereoisomer designed as E-configuration.

In fact, the following seven condensation products were obtained:

1-(E)-methyl 2-(3-(2-(allyloxy) phenyl) acryloyl) pent-4-enoate

2-(E)-methyl 5-(2-(allyloxy) phenyl)-3-oxo-2-(prop-2-ynyl) pent-4-enoate

3-(E)-methyl 2-(3-(2-(but-3-enyloxy) phenyl) acryloyl) pent-4-enoate

4-(E)-methyl 5-(2-(but-3-enyloxy) phenyl)-3-oxo-2-(prop-2-ynyl)pent-4-enoate

5-(E)-methyl 2-(3-(2-(pent-4-enyloxy) phenyl) acryloyl) pent-4-enoate

6-(E)-methyl 3-oxo-5-(2-(pent-4-enyloxy) phenyl)-2-(prop-2-ynyl)pent-4-enoate

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