Synthesis of Chalcones: A new High-yield and Substituent-independent Protocol for an Old structure

Author

Lyngsøe Poulsen, Martin

Abstract

The chalcone core scaffold was first synthesized by Claisen and Claperède in 1881 and have ever since drawn attention from an interdisciplinary combination of organic-,medicinal-, and biochemists, in order to explore the full potential of this scaffold. Many of these compounds have shown to be easy to modify, from the simple aromatic character, while also inducing endless opportunities for these modifications. The chalcone derivatives have been reported to have a wide range of therapeutic effects such as anticancer, antioxidants, anti-inflammatory, antihypertensive, antimalarial, antiviral, antiprotozoal, cardiovascular activity, and mutagenic properties. Due to their diversity, low cost, and easy modifications they are still the origin for the formation of important biological compounds. However, the formation of this simple scaffold is not yet stated in one generalized procedure, rather multiple approaches exit, some more complex than others all producing mixed results.
Prior work from the GQF group addressed the need for a consistent and effective procedure for various chalcones, since the chalcone formation was the limiting step in a multistep synthesis. Here, the aldolic condensation showed limitations whereas the Wittig approach demonstrated possibilities.
This work seeks to elucidate the full perspective of the limitations of the traditional aldolic condensation in the formation of a diverse family of chalcone derivatives.
Secondly, it aims to establish the Wittig procedure, based on prior work, as a general procedure for chalcone formation that can overrule the traditional procedure, in a general and green fashion. This simple generalization is needed and will simply further research in this field.

Director

Borrell Bilbao, José Ignacio

Degree

IQS SE - Master’s Degree in Pharmaceutical Chemistry

Date

2022-07-08