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Reactions of nitrile oxides and nitrile imines with 4‐arylidene‐2‐phenyl‐5(4 H )‐thiazolones
Author(s) -
CoutouliArgyropoulou Evdoxia,
Thessalonikeos Elisavet
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001198
Subject(s) - nitrile , chemistry , regioselectivity , isoxazole , cycloaddition , nucleophile , ring (chemistry) , medicinal chemistry , pyrazole , nucleophilic addition , structural isomer , organic chemistry , catalysis
Nitrile oxides 2a , b and nitrile imines 2c – e are added to the C C bond of 4‐arylidene‐2‐phenyl‐5(4 H )‐thiazolones 1 to afford spiro‐isoxazolines 3a – d and spiro‐pyrazolines 3e – j , respectively. The cycloaddition reactions are regioselective and only one of the two possible regioisomers is isolated. Reactions of the cycloadducts with nucleophiles lead to isoxazole and pyrazole derivatives 8 and 10 by opening of the thiazolone ring.