Selective instability of trifluoromethyl linked to carbon. A prerequisite for new heterocyclizations with ethyl 4,4,4‐trifluoroacetoacetate arylhydrazones | Zendy

Pilgram Kurt H. | Zendy; Skiles Richard D. | Zendy

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Selective instability of trifluoromethyl linked to carbon. A prerequisite for new heterocyclizations with ethyl 4,4,4‐trifluoroacetoacetate arylhydrazones

Author(s) -

Pilgram Kurt H.,

Skiles Richard D.

Publication year - 1988

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.5570250120

Subject(s) - chemistry , sodium hydride , trifluoromethyl , sodium ethoxide , deprotonation , sodium fluoride , fluoride , ethanol , medicinal chemistry , hydride , bicyclic molecule , sodium , ion , organic chemistry , inorganic chemistry , hydrogen , alkyl

Highly functionalized pyrazoles, 2 , and 1 H ‐pyrazolo[3,4‐ d ]pyridazinones 3 have been obtained in moderate yields from ethyl 4,4,4‐trifluoroacetoacetate o ‐chlorophenylhydrazones 1 by treatment with sodium hydride in aprotic solvents. Treatment of 2 and 3 with sodium ethoxide in ethanol gave bicyclic 5‐(5‐oxopyrazol‐3‐yl)‐pyrazolones 4 and 5 in high yields. The reactions of 1 with sodium hydride which are accompanied by the loss of fluoride ion from one trifluoromethyl group implicate the anchimeric assistance of an N ‐deprotonated anion of 1 in the initial reaction step.

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