Recent applications of aminouracil in multicomponent reactions

Abstract

6-Aminouracil and its derivatives are versatile heterocyclic compounds and are frequently employed to synthesize a wide array of fused uracils annulated with other heterocyclic rings which can serve to address biological and pharmacological targets. Multicomponent reactions (MCRs) are important in the synthesis of natural products and pharmaceuticals by forming heterocyclic molecular frameworks with generally high atom-economy in a single reaction step. This review embraces various modern synthetic strategies, summarizing recent research developments providing fused 6-aminouracil derivatives and to highlight the progress based on MCRs between 2015 and 2020.

Donor–Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-b]azepines Synthesis

“…Nevertheless, the reactivity of 6-aminouracils themselves toward electrophiles is similar to that of typical enamines . However, on the contrary to enamines, bearing a tertiary amino group, 6-(alkyl)­aminouracils can be used not only as C -nucleophiles but also as C , N -dinucleophiles . The combination of this binucleophilic reactivity with the ability of DA cyclopropanes to serve as 1,4-dielectrophiles , allows these starting compounds to be used for synthesizing seven-membered rings (substituted azepines), annulated to the uracil moiety.…”

“…Our interest in this reaction was additionally stimulated by a broad scope of bioactivity of related pyrimidine-2,4-dione derivatives . Thus, alogliptin and trelagliptin are used as antidiabetic drugs: aminometradine is a weak diuretic; lenacil is applied as a herbicide (Figure ), etc.…”

Synthesis, identification of some new 1,2,4-triazole derivatives from 6-amino-1,3-dimethyluracil and evaluation of their molecular docking, Anti-oxidant and experimental

“…aqueous NaOH solution (15-20 mL.) for (10)(11)(12) hours. The reaction of the mixture has cooled to room temperature, poured into ice-cold water.…”

“…The precipitate was recrystallized from ethanol to give crystals. Some of the physical properties of compound [10] and FTIR spectral data are listed in table-2. Antioxidant activity (DPPH radical scavenging assay) (24,25) The antioxidant activity of compounds (1-10) was determined using the stable DPPH free radical and a standard procedure.…”

“…The most significant nucleophilic activity is observed at position 3. This compound is easily synthesized into fused annulated compounds with other materials and polycyclic compounds with biological targets such as pyrido-, pyrrolo-, and pyrimido-pyrimidines [10][11] . These derivatives have demonstrated a remarkable range of pharmacological and biological activities, including antimicrobial [11] activity, antibacterial activity 12 , anti-influenza avius activity 13 , anti-neuroinflammatory activity 14 , antioxidant activity 15 , anticancer activity 16 , and anti-HIV activity 17 .…”