Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1,2,3-triazolyl appended 4,5-unsaturated L-ascorbic acid derivatives (CROSBI ID 236206)
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Podaci o odgovornosti
Meščić, Andrijana ; Šalić, Anita ; Gregorić, Tomislav ; Zelić, Bruno ; Raić-Malić, Silvana
engleski
Continuous flow-ultrasonic synergy in click reactions for the synthesis of novel 1,2,3-triazolyl appended 4,5-unsaturated L-ascorbic acid derivatives
A combination of flow chemistry and batch-based synthetic procedures has been successfully applied to the assembly of novel 4, 5-unsaturated L-ascorbic acid series 6a–6n with diverse C-6- substituted 1, 2, 3- triazole moiety. 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 6a–6n under both micro-flow and batch conditions. 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 of 6a–6n. Moreover, the synergistic use of microreactor technology and ultrasonic irradiation highlights the sustainable eco- friendly aspect of utilized method.
flow chemistry ; L-ascorbic acid ; click cemistry
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Povezanost rada
Kemija, Kemijsko inženjerstvo