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The preparation of perfluoroaryl substituted isoxazoles via nucleophilic aromatic substitution with lithioalkylisoxazoles
Author(s) -
Xia Xiongbing,
Knerr Gary,
Natale N. R.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290539
Subject(s) - chemistry , substituent , metalation , moiety , hexafluorobenzene , nucleophilic aromatic substitution , nucleophilic substitution , amide , medicinal chemistry , substitution reaction , substitution (logic) , stereochemistry , organic chemistry , benzene , computer science , programming language
Abstract The lithioalkylisoxazoles obtained from C‐5 lateral metalation of alkylisoxazoles, 1 , add to hexafluorobenzene. When the C‐4 substituent was an electron withdrawing tertiary amide moiety, the yields were highest for mono‐perfluoroarylation to give 5‐pentafluorophenylmethylisoxazoles, 2 .