Ultrasonic-Promoted Three-Component Synthesis of Some Biologically Active 1,2,5,6-Tetrahydropyrimidines

Abstract

Multicomponent reactions and organic synthesis with ultrasonic activation have been used as key methods for the synthesis of tetrahydropyrimidine derivatives. The three-component condensation of 1,3-diarylprop-2-en-1-one with ammonia and aldehydes/acetone or N-substituted γ-pyridones under ultrasonic irradiation was developed as a rapid and efficient solution-phase method for the high-yielding preparation of 2-aryl(hetaryl)-4,6-diaryl-1,2,5,6-tetrahydropyrimidines and 2,4-diaryl-1,5,9-triazaspiro[5.5]undec-1-enes. The described synthetic protocol provides rapid access to novel and diversely substituted tetrahydropyrimidines libraries. The simple, primary biological screening showed 98% of inhibitory activity against Mycobacterium tuberculosis for one of tetrahydropyrimidines synthesized.

Efficient Synthesis of 2,4-diamino-6-phenyl-1,4,5,6-tetrahydropyrimidine-5-carbonitriles

“…Zhao et al were synthesized fluoroalkylated multifunctional 1,2,3,4-tetrahydropyrimidines for the first time by the reaction of 3-fluoroalkyl-3-anilinoacrylic acid esters with primary amines and formaldehyde under mild conditions 13 . Muravyova et al have carried out multicomponent reactions with ultrasonic activation used as key methods for the synthesis of tetrahydropyrimidine derivatives [14][15] .…”

Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin

“…Pyrimidine derivatives are versatile building blocks in synthetic organic chemistry and many bioactive molecules [1][2][3][4] with pyrimidine skeleton served as M1 muscarinic receptor agonists for the treatment of Alzheimer's disease [5,6] and human immune deficiency virus (HIV) protease inhibitors [7]. Pyrimidine moiety is an important class of N-containing heterocyclic system [8,9], which exhibits wide spectrum of biological activities such as bactericidal [10], fungicidal [11], analgesic [12], anti-hypertensive [13], antimicrobial [14] and anti-infective properties [15].…”

An Efficient Synthesis of Isoxazoles and Pyrazoles under Ultrasound Irradiation

“…Ultrasonic irradiation, as a powerful tool in modern chemistry for the organic synthesis, has attracted more attention from organic chemists . The ultrasonic irradiation with its advantages of convenient operation, mild reaction conditions, short reaction times, and high efficiency has become particularly popular in recent years, and numerous examples under this condition for constructing heterocyclic compounds have been reported in the literatures .…”