Pseudo-Five-Component Reaction between 3-Formylchromones, Meldrum’s Acid, Isocyanides and Primary Arylamines: Diversity-Oriented Synthesis of Novel Chromone-Containing Peptidomimetics

Abstract

An efficient and practical method has been developed for the diversity-oriented synthesis of chromone-containing tripeptides via pseudo-five-component reaction between 3-formylchromones, Meldrum's acid, isocyanides and primary aromatic amines for the generation of a wide range of structurally interesting and pharmacologically significant compounds at ambient temperature. It is worth mentioning that in the course of this reaction, five new bonds (two C-C bonds, two C-N bonds and one C═O bond) are formed. In the present reaction three amide bonds are newly formed.

Diastereoselective One‐Pot Synthesis of Coumarin‐4‐carboxamido‐3‐esters via a Four‐Component Isocyanide‐Based Reaction and Molecular Docking Study

“…Continuing our efforts directed toward the straightforward preparation of biologically interesting heterocycles through IMCRs,, in this study, we report a facile and efficient four‐component stereoselective reaction between 2‐hydroxybenzaldehyde (salicylaldehyde) 1 , malonic acid 2 , alkyl or aryl isocyanides 3 and various alcohols 4 for the preparation of a new series of coumarin‐4‐carboxamido‐3‐esters 5 (Scheme ). Although in some research IMCRs method was utilized for the synthesis of dihydrocoumarin derivatives,, to the best of our knowledge, there is no report on the preparation of dihydrocoumarins via four‐component condensation reactions of 2‐hydroxybenzaldehyde with malonic acid in the presence of isocyanides and alcohols.…”

“…Continuing our efforts directed toward the straightforward preparation of biologically interesting heterocycles through IMCRs, [34,35] in this study, we report a facile and efficient fourcomponent stereoselective reaction between 2-hydroxybenzaldehyde (salicylaldehyde) 1, malonic acid 2, alkyl or aryl isocyanides 3 and various alcohols 4 for the preparation of a new series of coumarin-4-carboxamido-3-esters 5 (Scheme 2).…”

Synthesis and Chemical Reactivity of 4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

“…In case of p-C 6 H 4 (CH 2 Br) 2 , 108 and 109 were obtained [68] On the other hand, treatment of primary amines 115 in the presence of alkyl or arylisocyanide 116 with a mixture of 4-oxo-4H-1-benzopyran-3-carboxaldehyde 1 and Meldrum's acid in dry CH 2 Cl 2 at room temperature atom economically afforded 117 in 75-95% yield. It is believed that the compound contains three peptide linkages formed through Knoevenagel condensation [70] (Scheme 40).…”

Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study

“…The abundance and availability of heterocyclic compounds in nature, particularly in plants as well as the broad spectrum of their applications have attracted researcher's attention for many years. Among oxygen‐containing heterocycles, chromone nucleus and its derivatives are frequently used as key components in different fields, especially for the design and discovery of new pharmacologically active compounds because of their numerous bioactivities including antiviral, anti‐tumour, anti‐inflammatory, and anti‐anaphylactic activity . They also recognized as antioxidants, anti‐coagulant, pigments, photo‐active materials, antiplatelet, antifungal, antibacterial, anti‐HIV, anti‐ulcers, biocidal, and immune‐stimulators .…”