Multicomponent Reactions in the Synthesis of Complex Fused Coumarin Derivatives

Abstract

Background: Coumarin is an important class of natural products with applications in different areas of knowledge. Due to its importance, several methodologies and strategies have been developed for the synthesis of different classes of compounds containing this nucleus. Objective: The aim of this review is to cover in the last five years the complex fused coumarin derivatives synthesized in one-pot three-component reactions. Conclusion: Considering that multicomponent reactions are a powerful tool to produce simple and complex compounds in one or few steps with high selectivity and yields while following the green chemistry principles.

Effective Synthesis and Biological Evaluation of Functionalized 2,3-Dihydrofuro[3,2-c]coumarins via an Imidazole-Catalyzed Green Multicomponent Approach

“…Herein, with an aim to envisage their therapeutic usage, we set out to optimize an eco-friendly one-pot strategy to synthesize varied functionalized DHFCs along with their novel derivatives targeting in silico and in vitro-based structure–activity analysis. Therefore, in continuation of our unwavering interest in developing an environmentally friendly multicomponent reaction, − we investigated the combined chemistry of 4-hydroxycoumarin, aldehyde, and α-bromoacetophenone, catalyzed by imidazole using only water as a green solvent. In our effort to overcome drawbacks from the previous report and formulate an efficient green approach, for the first time, we disclose here an imidazole-catalyzed simplest technique in aqueous media at moderate temperature for the synthesis of a densely substituted DHFC framework.…”

Synthesis of Chromeno[3,4-b]piperazines by an Enol-Ugi/Reduction/Cyclization Sequence

“…Thus, piperazines and pyrazines have been synthesized by modified Ugi condensations [20] and post-condensation transformations of Ugi [7,[21][22][23] or Ugi-Smiles products [24,25]. Different multicomponent strategies have also been used in the synthesis of polycyclic coumarins [26].…”

Enantioselective synthesis of coumarins catalyzed by an isosteviol‐derived tertiary amine‐squaramide catalyst

“…[1][2][3] Consequently, the asymmetric methodology of preparing such heterocyclic compounds has been a long-standing interest. [4][5][6] The direct asymmetric Michael addition of coumarin and β,γ-unsaturated α-ketoesters, 7 which have special advantages owing to high reactivity and potential conversion to a range of different functionalities, is considered to be one of the most convenient conversion pathways. As early as in 2003, Jørgensen and co-workers reported the first Michael reaction of cyclic 1,3-dicarbonyl compounds to β,γ-unsaturated α-ketoesters catalyzed by chiral bisoxazoline-copper (II) complexes, quantitative yields and up to 92% ee were obtained.…”