3-Phenyl-5-(3,5-dichlorophenyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (III, R = H) and 3-phenyl-5-(3,5-dichlorophenyl)-6a-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (IV, R = CH3) were prepared by 1,3-dipolar cycloaddition of substituted benzonitrile oxides I to N-(3,5-dichlorophenyl)maleimide (I, R = H), or its methyl derivative II (R = CH3). Cycloaddition to compound II (R = CH3) proceeded regiospecifically. Reduction of IVg with NaBH4 was regio- and stereoselective to yield the hydroxylactams VIIg, VIIIg, and IXg. Antifungal activity of several products was worse than that of commercial preparations.

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The reduction of condensed imides 1 with sodium borohydride proceeds regio-and stereoselectively to yield the hydroxylactams 2, 3 and 4. AM1 calculations of the reactants and products reveal that the regiochemistry of the reductions seems to be controlled by both electronic and steric effects. The regio-and stereoselectivity of the reductions are drama-