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A Convenient Approach to CF 3 ‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one
Author(s) -
Bazhin Denis N.,
Kudyakova Yulia S.,
Röschenthaler GerdVolker,
Burgart Yanina V.,
Slepukhin Pavel A.,
Isenov Maksim L.,
Saloutin Victor I.,
Charushin Valery N.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500737
Subject(s) - chemistry , trifluoromethyl , furan , hydroxylamine , medicinal chemistry , nucleophile , quinoxaline , organic chemistry , yield (engineering) , hydrazone , catalysis , alkyl , materials science , metallurgy
New synthetic routes to trifluoromethylated N‐heterocycles based on condensations of 2‐methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2 H )‐one with bifunctional N‐nucleophiles are described. For the first time, trifluoromethyl‐containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one‐pot strategy based on reactions of 5‐(trifluoromethyl)furan‐3(2 H )‐one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan‐3(2 H )‐one with ureas proceeded under mild conditions to furnish 1 H ‐furo[2,3‐ d ]imidazol‐2(3 H )‐one derivatives in good yield. Further, a trifluoromethyl‐containing quinoxaline derivative was obtained by condensation of furan‐3(2 H )‐one with ortho ‐phenylenediamine.
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