4.4 Article

Synthesis of pyrazoles with fluorinated side-chain by cyclization of fluoroalkylated triketides

Journal

TETRAHEDRON
Volume 69, Issue 16, Pages 3459-3464

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.02.059

Keywords

Cyclizations; Dianions; Organofluorine compounds; Tautomerism; 1,3,5-Tricarbonyl compounds

Funding

  1. State of Mecklenburg-Vorpommern
  2. EU (EFRE program)
  3. Volkswagenstiftung [Az86223]

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The cyclization of fluoroalkylated 3,5-dioxoesters with hydrazines, carried out in glacial acetic acid, afforded pyrazines with fluoroalkylated side-chain. The cyclization of 3,5-dioxoesters with hydroxylamine afforded hydroxylated fluoroalkylated dihydroisoxazoles. All reactions proceeded with good to very good regioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

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