Vertical Diversity-Oriented Synthesis with Dibenzylideneacetones. Multivariate Optimization and Diversity Exploration.

Abstract

DOS was planned from dibenzylideneacetone to generate compound library with structural diversity, which can undergo further transformations. In the presented work, dibenzylideneacetone was cyclized under Robinson Annulation reaction. The resulting cyclization product was optimized using Multivariate response surface method. Response surface analysis helped to determine both significant variables used during the optimization process and to generate a model describing the variation of response according to the experimental variables. The Robinson Annulation product was studied in a range of transformations, for instance Hydrogenation, Krapcho decarboxylation, inverse electron demand Diels-Alder, Luche reduction and Alkylation reaction. All the attempted reactions were found successful, except reduction and cycloaddition reactions. Further work on unsuccessful reactions could not be carried out due to time constraints. Various new compounds were synthesized during this work. Dibenzylideneacetone can play various functions in synthetic chemistry as precursor to other compounds. It is used to make ligands, for instance dibenzylideneacetonedipalladium (0) which is utilized as a homogeneous catalyst in organic synthesis. Dibenzylideneacetone can be used to synthesize heterocyclic organic compounds. There is no available research conducted to explore its benefits to synthesize compound libraries.