Journal
POLYCYCLIC AROMATIC COMPOUNDS
Volume 42, Issue 3, Pages 951-959Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10406638.2020.1757473
Keywords
Active methylenes; ball-milling; boronic acids; one-pot reaction; 123-triazoles
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Funding
- Research Council of the University of Mazandaran
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In this study, a mild and efficient one-pot synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a three-component reaction under ball-milling conditions was reported. The optimized reaction conditions yielded a wide variety of derivatives in high yields, offering advantages such as high product yields, short reaction time, and simple work-up procedure.
In this study, we report a mild and efficient one-pot synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via a three-component reaction of aryl boronic acids with sodium azide and active methylene compounds under ball-milling condition. In order to determine optimized reaction conditions, several grinding auxiliaries (basic, neutral and acidic alumina, silica gel, K10 and KSF), bases (DBU, DABCO, piperidine, triethylamine, potassium t-butoxide and potassium carbonate) and copper salts under ball-milling conditions were examined. Using the optimized condition procedure, a wide variety of 1,4,5-trisubstituted 1,2,3-triazole derivatives were prepared in very good yields. All products were well-characterized by H-1-NMR and C-13-NMR spectroscopy. This environmentally friendly protocol offers several advantages including high yields of products, relatively short reaction time and simple work-up procedure.
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