title: Use of iodoacetylene as a dipolarphile in the synthesis of 5-iodoisoxazole derivatives.
abstract: Iodoacetylene 1 was prepared in situ from the reactions of ethynylmagnesium bromide or tributyl(ethynyl)tin with iodine. It was used as a dipolarphile in the [2 + 3] cyclization reaction with 1,3-dipolar nitrile oxide derivatives to produce 2-(5-iodoisoxazol-3-yl)pyridine 2 and 3-(4-fluorophenyl)-5-iodoisoxazole 8 in good yield (70-90%). Subsequently, several 5-substituted isoxazole derivatives 3 were obtained by Pd-catalyzed reactions. [reaction: see text]
authors.affiliation: D-45L, Chemical Process Research, Global Pharmaceutical Research and Development, Abbott Laboratories, North Chicago, IL 60064-4000, USA.
authors.forename: Y Y
authors.initials: YY
authors.lastname: Ku
authors.forename: T
authors.initials: T
authors.lastname: Grieme
authors.forename: P
authors.initials: P
authors.lastname: Sharma
authors.forename: Y M
authors.initials: YM
authors.lastname: Pu
authors.forename: P
authors.initials: P
authors.lastname: Raje
authors.forename: H
authors.initials: H
authors.lastname: Morton
authors.forename: S
authors.initials: S
authors.lastname: King