Click chemistry-based strategies for the synthesis of 2-amino-alkyl-1,2,3-triazole-1,4-naphthoquinone derivatives make it possible to obtain desired products from 1,4-naphthoquinone (1,4-NQ), and bio-based lawsone, nor-lapachol and lapachol. The first route (Strategy A) starting from 1,4-NQ and amino alcohols, then 2-amino-alkyl-1,4-NQ alcohols, were tosylated. The azide ion displaced the tosylate group to afford 2-azide-alkyl-1,4-NQ, which was submitted to a copper-catalyzed azide alkyne cycloaddition (CuAAC) condition. The triazole-naphthoquinones were obtained in an overall yield of roughly 47%. Another pathway (Strategy B) substituted bromo-alkyl-phthalimides using NaN3 as the nucleophile, sequential CuAAC and deprotection of phthalimide group with hydrazine producing amino-triazoles. The subsequent reaction with 1,4-NQ produced 2-amino-alkyl-1,2,3-triazole-1,4-NQ derivatives in an overall yield of 45-76% in four steps. After we developed these two strategies, linear synthesis (Strategy A) was chosen to prepare 2-[(2-(1H-1,2,3-triazol-1-yl)ethylamino)]-3-(3-methylpropenyl)-1,4-naphthoquinones from lawsone with an overall yield of approximately 27% in six steps. On the other hand, convergent synthesis (Strategy B) was employed for the synthesis of 2-[(4-phenyl-1H-1,2,3-triazol-1-yl)alkyl-amino)]-3-(3-methylbut-2-en-1-yl)-1,4-naphthoquinones from the reaction between 2-methoxy-lapachol with amino-triazoles with a global yield of about 21%. These synthetic strategies might lead us to new opportunities to build small-molecule libraries for future biological exploration.

Neste trabalho, a preparação de vários glicosídeos triazólicos a partir da reação entre a azida de 2,3,4,6-tetra-O-acetil-β-D-glicopiranosila e alcinos terminais foi desenvolvida em moderados a excelentes rendimentos (63-99%). Em todas as etapas de reação foi aplicada a energia de ultrassom para aumentar a reatividade química. Adicionalmente, os compostos conjugados com benzoeterociclos revelaram potente atividade anti-inflamatória.

In this work, the preparation of various glucosyl triazoles from a reaction between 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide and terminal alkynes was developed in moderate to excellent yields (63-99%). Ultrasound energy was applied at each step of the reaction to increase chemical reactivity. In addition, the compounds conjugated with benzoheterocycles moieties revealed potent anti-inflammatory activity.

Uma série de derivados 1,2,3-triazólicos foi sintetizada a partir de N-alquilftalimida-azidas (A1 -A4) e alcinos (a-e) sob irradiação de ultrassom na presença de CuI, Et3N 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 (A1 -A4) and alkynes (a-e) under ultrasound irradiation in the presence of CuI, Et3N and DMF as solvent. The present protocol afforded 18 new 1,2,3-triazoles (1-4) in good-to-excellent yields (67-98%).

Uma nova série de derivados 1,2,3,-triazólicos foi sintetizada a partir de ftalimidas e alcinos terminais na presença de quantidade catalítica de CuI. O presente protocolo forneceu 1,2,3-triazóis em moderados a bons rendimentos (44-89%)

A new series of 1,2,3-triazole derivatives have been synthesized from phthalimides and terminal alkynes in the presence of a catalytic amount of CuI. The present protocol affords 1,2,3-triazoles in moderate to good yields (44-89%)

This is a report on an efficient and rapid synthesis of amidoximes using ultrasound irradiation with appropriate nitrile and hydroxylamine hydrochloride in water/ethanol. This new synthetic methodology is compared with previously known methods. The main advantages of the process reported are shorter reaction times, easier work-up, and good yield.

Uma síntese fácil, eficiente e rápida de N-benzoil-(e benzoil N-substituída)-N,N'-dialquiluréias foi realizada com bons rendimentos em condições livre de solvente. Primeiramente, a reação entre um ácido carboxílico e uma carbodiimida dissubstituída foi feita empregando radiação de microondas, e depois a mesma reação foi realizada sob aquecimento convencional. Os rendimentos são comparáveis em ambos os casos.

An easy, efficient and quick synthesis of N-benzoyl-(and N-substituted benzoyl)-N,N'dialkylureas, in good yields, under solvent-free conditions is described. First, the reaction between a carboxylic acid and a disubstituted carbodiimide was carried out employing microwave radiation, and later on the same reaction was performed separately under dry heating without any radiation. The yields are comparable in both cases.