Journal
TETRAHEDRON
Volume 73, Issue 27-28, Pages 3959-3965Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.05.065
Keywords
Continuous flow microreactor; 1,2,3-Triazole; Nitroalkene; Acid promote; In-tube retention time gradient
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Funding
- National Natural Science Foundation of China [21235004, 21175080]
- Ministry of Science and Technology [2013ZX09507005]
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The N-unsubstituted 4-aryl-1H-1,2,3-triazoles were synthesized via the acetic acid promoted cycloaddition between P-nitrostyrenes with sodium azide under transition-metal-free conditions in a continuous flow microreactor. The continuous-flow microreactor provided a safe environment for the dangerous reagents NaN3 and nitroalkene, and offered such a rapid procedure that the triazoles were formed in less than 4 min. In addition, the excess sodium azide was quenched by the by-product HNO2 in the presence of acetic acid. The scale-up experiment proved again that the yield did not drop in the flow reaction. Moreover, the synthesis of N-unsubstituted 1,2,3-triazole was also explored via a one pot reaction with aldehyde, nitromethane and sodium azide, and this reaction was monitored with an in-tube retention time gradient (IT-RIG) technology, which may be a novel application of the continuous-flow microreactor. (C) 2017 Elsevier Ltd. All rights reserved.
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