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Paper | Regular issue | Vol 71, No. 2, 2007, pp.289-303
Published online, 22nd December, 2006
DOI: 10.3987/COM-06-10918
Spiroheterocycles from the Reaction of Arylnitrile Oxides with Some (Z)-3-Arylidene-2(3H)-benzofuranones. New Access to Orthohydroxyphenylisoxazoline Esters

Moheddine Askri, Naffa Jgham, Mohamed Rammah, Kabula Ciamala,* Karin Monnier-Jobé, and Joël Vebrel

*Laboratory of Material Chemistry and Interfaces, UFR of Science and Technology, 16 Route de Gray, F-25030 Besançon, France

Abstract

Some 4-substituted arylnitrile oxides and (Z)-3-arylidene-2(3H)-benzofuranones undergo 1,3-dipolar cycloaddition reactions to give exclusively spirodihydroisoxazoles. These spiroadducts have be opened to the corresponding ethyl 3,4-diaryl-5-(orthohydroxyphenyl)-4,5-dihydroisoxazoline-5-carboxylates by the action of concentrated hydrochloric acid at reflux in ethanol.