Abstract
A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular structure of the title compound was characterized on the basis of spectroscopic evidence, using FTIR, HRESI-MS, 1H- and 13C-NMR, and 2D NMR.
Highlights
A Biginelli reaction is an acid-catalyzed multicomponent condensation of three reagents that are originally from aromatic aldehyde, urea, and ethyl acetoacetate using hydrochloric acid as a catalyst [1]to furnish dihydropyrimidinone (DHPM) derivatives [2,3]
To furnish dihydropyrimidinone (DHPM) derivatives [2,3]. This reaction possesses a great synthetic potential to be extended via the use of new functional reagents. This reaction served successfully to be applied for the preparation of various DHPM derivatives, including a fused pyrimidine derivative and in particular azolopyrimidines [4,5,6]
The synthesis of derivative compounds with a tetrazolo[1,5-a]pyrimidine core is of considerable interest for both organic synthesis and medicinal chemistry
Summary
A Biginelli reaction is an acid-catalyzed multicomponent condensation of three reagents that are originally from aromatic aldehyde, urea, and ethyl acetoacetate using hydrochloric acid as a catalyst [1]. To furnish dihydropyrimidinone (DHPM) derivatives [2,3] This reaction possesses a great synthetic potential to be extended via the use of new functional reagents. Compounds displaying the tetrazolo[1,5-a]pyrimidine core moiety are well known to show a wide range of pharmacological activities, such as antituberculosis, anticonvulsant, and antidepressant properties. They exhibit activities such as sodium channel blocking, the inhibition of human neutrophil elastase [7], and hypoglycemic [8], antibacterial [9], and anti-oxidant [10] properties. The presence of a morpholinophenyl group in an organic molecule is known to be responsible for certain biological activities, such as antibacterial [11], anticancer [12], and anti-oxidant [13] properties
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