Synthesis of N-substituted phthalimidoalkyl 1H-1,2,3-triazoles: a molecular diversity combining click chemistry and ultrasound irradiation

Abstract

Uma série de derivados 1,2,3-triazólicos foi sintetizada a partir de N-alquilftalimida-azidas (A 1 -A 4 ) e alcinos (a-e) sob irradiação de ultrassom na presença de CuI, Et 3 N e DMF como solvente. O presente protocolo forneceu 18 novos 1,2,3-triazóis (1-4) em rendimentos de bons a excelentes (67-98%).A series of 1,2,3-triazole derivatives was synthesized from N-phthalimidoalkyl-azides (A 1 -A 4 ) and alkynes (a-e) under ultrasound irradiation in the presence of CuI, Et 3 N and DMF as solvent. The present protocol afforded 18 new 1,2,3-triazoles (1-4) in good-to-excellent yields (67-98%).

Advantages of the use of heterogeneous catalyst for Huisgen cycloaddition reaction: synthesis and application of new metalorganic material capable of regeneration and reuse

“…The Scheme 2 shows the mechanism proposed to create the reaction using [Cu(4,4'-dipy)]Cl complex. Based on data in literature indicating that Cu(I) catalyzed alkyne-azide coupling begins with π complex A (Scheme 2), this first step was also proposed for the [Cu(4,4'-dipy)]Cl complex [30][31][32][33][34][35][36] . Some works suggest that an energetic compensation can occur depending on the solvent Eclética Química Journal, vol.…”

“…The copper(I) catalyst promotes the formation of 1,2,3-triazoles from azides and terminal alkynes, with high yields, mild conditions and excellent regioselectivity 30,31 . Generally, in this reaction, the desired product is isolated by chromatography and the copper(I) residues are removed by an extraction process, using successive washes with ammonium hydroxide 32,33 .…”

Antileishmanial activity of 4-phenyl-1-[2-(phthalimido-2-yl)ethyl]-1H-1,2,3-triazole (PT4) derivative on Leishmania amazonensis and Leishmania braziliensis: In silico ADMET, in vitro activity, docking and molecular dynamic simulations

“…The purity of fractions was monitored in TLC analysis on GF 254 plate. The azide and 1,2,3-triazoles compounds were prepared according to the procedure described by Silva et al (2012).…”

1,2,3- Triazoles: general and key synthetic strategies

“…Ultrasonic energy increases system efficiency by activating the catalyst surface area and removing deposited impurities. 204 The use of ultrasonic energy has been reported by several research groups for the preparation of 1,2,3-triazoles from CuAAC reactions, [205][206][207] in which different sources of Cu(I) or Cu(II) were used.…”