Non-catalytic multicomponent rapid and efficient approach to 10-(2,4,6-trioxohexahydropyrimidin-5-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-ones from salicylaldehydes, dimedone, and barbituric acids

Abstract

Non-catalytic multicomponent reaction of salicylaldehydes, dimedone, and barbituric acids initiated by reflux in ethanol results in the fast (5 min) and efficient formation of substituted tetrahydro-1H-xanthen-1-ones in 90-95 % yields. The developed fast multicomponent approach to the substituted tetrahydro-1H-xanthen-1-ones, which are known as medicinally relevant substances such as antibiotics, enzyme inhibitors, and anticancer drugs, is beneficial from the viewpoint of diversity-oriented multigram-scale processes and represents fast, efficient, and environmentally benign synthetic concept for multicomponent reaction strategy. Graphical abstract

Recent applications of barbituric acid in multicomponent reactions

“…134 The reactions were performed in ethanol under mild and metalfree conditions. 136 A catalyst-free chemical protocol for the construction of pyrimidine containing poly- The antimicrobial activity of the synthesized compounds was studied and the results revealed that compounds having thioxopyrimidinedione in combination with bisthiadiazole unit exhibited high activity. 135 Non-catalytic three-component reaction was also reported resulted in the formation of related products in 90-95 % yields.…”

Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H‐Pyrano‐[4,3‐b]pyran‐5‐one and 4,6‐Dihydro‐5H‐pyrano‐[3,2‐c]pyridine‐5‐one Scaffolds

“…The thermal activation, which ensured success earlier , led to 4 H ,5 H ‐pyrano[4,3‐ b ]pyran 4a in 87% yield in only 3 min ( Table , Entry 8 ). In this case, the mortar was replaced by a flask, and the reaction was carried out at 78 °C using a magnetic stirring bar.…”

Fast highly efficient 'on-solvent' non catalytic cascade transformation of benzaldehydes and 4-hydroxycoumarin into bis(4-hydroxycoumarinyl)arylmethanes

“…With the above results taken into consideration and the mechanistic data on non-catalytic 'domino' transformations [36][37][38] the following mechanism for the non-catalytic cascade transformation of benzaldehydes 1 and 4-hydroxycoumarin (2) into 3,3'-(arylmethylene)bis(4-hydroxy-2H-chromen-2-ones) 3 was suggested. The initiation step of the catalytic cycle is the thermal deprotonation of a molecule of 4-hydroxycoumarin 2 with the 4-hydroxycoumarin anion A formation (Scheme 2).…”

“…[34][35][36][37][38] Considering our results on the non-catalytic multicomponent and cascade transformation of C-H acids and carbonylcompounds [34][35][36][37][38] as well as the certain biomedical application of bis(4-hydroxycoumarinyl)arylmethanes mentioned above, we were prompted to design a convenient fast and facile non-catalytic methodology for the fast efficient cascade synthesis of substituted bis(4-hydroxycoumarinyl)arylmethanes based on cascade reaction of of benzaldehydes and 4-hydroxycoumarin.…”