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Fluorine-Sacrificial Cyclizations as an Access to 5-Fluoropyrazoles

✍ Scribed by Jean-Noël Volle; Manfred Schlosser

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 263 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200003)2000:5<823::aid-ejoc823>3.0.co;2-m

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✦ Synopsis

Methyl 3-methoxy-2-trifluoromethylacrylate 1, readily prepared by Wittig reaction from methyl 3,3,3-trifluoropyruvate, has been treated with a number of aryl-(or hetaryl-) hydrazines. Under mild base-catalysis, the resulting 3-hydrazinoacrylates 6 undergo consecutive hydrogen fluoride elimination and intramolecular nucleophilic addition to afford

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