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2‐Trifluoroacetyl‐1‐methoxycycloalkenes: A convenient precursor for the synthesis of geminated polymethylene trifluoromethyl substituted heterocycles
Author(s) -
Bonacorso Helio Gauze,
Costa Michelle Budke,
Cechinel Cleber André,
Sehnem Ronan Carlo,
Martins Marcos Antonio Pinto,
Zanatta Nilo
Publication year - 2009
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.66
Subject(s) - chemistry , trifluoromethyl , hydroxylamine hydrochloride , ring (chemistry) , pyrimidinones , organic chemistry , hydrochloride , quinoline , hydroxylamine , thiazole , hydrazine (antidepressant) , medicinal chemistry , chromatography , alkyl
This article describes the methodology that allows the simultaneous introduction of a trifluoromethyl group and a 7‐, 8‐, and 10‐membered cycloalkane ring fused to heterocyclic derivatives. A series of 10 geminated polymethylene trifluoromethyl substituted isoxazolines, pyrazoles, pyrimidinones, and a pyrazolyl‐quinoline were obtained in moderate to good yields from the reaction of three 2‐trifluoroacetyl‐1‐methoxycycloalkenes derived from cycloheptanone, cyclooctanone, and cyclododecanone with hydroxylamine hydrochloride, hydrazine hydrochloride, urea, and 7‐chloro‐4‐hydrazinoquinoline. J. Heterocyclic Chem., (2009).