The Me ester of 2-fluoro-3-methoxyacrylic acid and the corresponding acyl chloride were used for the efficacious synthesis of fluorine-bearing pyrazolones, pyrimidines, coumarines and benzothiopyranones. Depending on the C3F component and the conditions employed, the same cyclization partner (e.g., 2-aminothiophenol) may lead to two or even three different products. The condensation of phenylhydrazine with (Z)-2-fluoro-3-methoxy-2-propenoyl chloride gave (Z)-2-fluoro-3-methoxy-2-propenoic acid 2-phenylhydrazide. The cyclocondensation of the latter gave 4-fluoro-1,2-dihydro-1-phenyl-3H-pyrazol-3-one. [on SciFinder (R)]
Title
Versatile 2-Fluoroacrylic Building Blocks for the Synthesis of Fluorinated Heterocyclic Compounds
Published in
Tetrahedron
Volume
52
Issue
12
Pages
4403-10
Date
1996
ISSN
0040-4020
Note
CAN 124:317100
28-16
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chimie organique l'Universite,Lausanne-Dorigny,Switz.
Journal
written in English.
100-63-0 (Phenylhydrazine); 108-95-2 (Phenol); 108-98-5 (Thiophenol); 137-07-5 (2-Aminothiophenol); 6290-49-9 (Methyl methoxyacetate); 107940-08-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of fluoroacrylate building blocks for fluorinated heterocyclic compds.); 175609-69-5P; 175609-70-8P; 176173-17-4P; 176173-18-5P; 176173-19-6P; 176173-21-0P; 176173-22-1P; 176173-23-2P; 176173-25-4P; 176173-27-6P; 176173-28-7P; 176173-29-8P; 176173-30-1P; 176173-35-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of fluoroacrylate building blocks for fluorinated heterocyclic compds.); 51-21-8P; 704-60-9P; 176173-20-9P; 176173-24-3P; 176173-26-5P; 176173-31-2P; 176173-32-3P; 176173-33-4P; 176173-34-5P; 176173-36-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluoroacrylate building blocks for fluorinated heterocyclic compds.)
Record creation date
2006-03-03
