Journal
TETRAHEDRON
Volume 72, Issue 39, Pages 5880-5885Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.021
Keywords
Trifluoromethylpyrazole; [3+2] Cyclocondensation; Fluazolate; Regioselective; N-methylation
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Funding
- Taiwan Ministry of Science and Technology [MOST 103-2113-M-039-002-MY2]
- China Medical University (the Ministry of Education, the Aim for the Top University Plan)
- Chinese Medicine Research Center
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Starting from commercially available 2-chloro-4-fluorobenzoic acid 4, synthesis of fluazolate was achieved in up to 30% overall yield via the key procedure of either regioselective [3+2] cyclocondensation of trifluoromethyl-alpha,beta-ynone 2 with hydrazine hydrate or nucleophilic substitution-cyclization of trifluoromethyl-alpha,beta-dibromoenone 10 with hydrazine hydrate. (C) 2016 Elsevier Ltd. All rights reserved.
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