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2-Trifluoroacetyl-1-methoxycycloalkenes: A convenient precursor for the synthesis of geminated polymethylene trifluoromethyl substituted heterocycles

✍ Scribed by Helio Gauze Bonacorso; Michelle Budke Costa; Cleber André Cechinel; Ronan Carlo Sehnem; Marcos Antonio Pinto Martins; Nilo Zanatta

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 105 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.66

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✦ Synopsis

Abstract

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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).

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