engleski

Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1, 2, 3- triazolyl appended L-ascorbic acid derivatives

Flow chemistry technique performs a chemical reaction in a continuously flowing stream in a network of interconnecting tubes. Although click reactions are traditionally conducted in batch process, the progress toward increased sustainability that requires novel approaches with reduced environmental impact opened up in recent years continuous-flow as a novel alternative to conventional batch-based synthesis. Microreactor technology has the potential to revolutionize the pharmaceutical industry because the number of potential drug candidates that can be prepared and screened can be considerably increased, hence the likelihood of developing new drugs is considerably enhanced. [1] Realizing the benefits of flow chemistry and in continuation of our study towards the synthesis of 1, 2, 3-triazole-containing heterocycle pharmacophores [2, 3], we report herein the first Cu(I)-catalyzed 1, 3-dipolar cycloaddition of azido functionalized L-ascorbic acid derivative and selected alkynes to provide target 1, 2, 3- triazolyl appended 4, 5- didehydro-5, 6-dideoxy-L- ascorbic acid library, as molecules with unique biological properties, using innovative ultrasound and continuous flow hybrid system (Figure 1). Implementation of ultrasound with flow chemistry accelerated hour- scale reaction conditions in batch to the minute range in micro- flow device and considerably improved the yields for the flow syntheses. Moreover, the synergistic use of microreactor technology and ultrasonic irradiation highlights the sustainable eco- friendly aspect of utilized method.

microreactor, 1, 2, 3-triazole ; L-ascorbic acid ; click chemistry

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