The Journal of Organic Chemistry

Spiroheterocycles from the reaction of nitrile oxides with 3-methylenephthalimidines

RK Howe, BR Shelton

Index: Howe, Robert K.; Shelton, Becky R. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4603 - 4607

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Citation Number: 113

Abstract

In explorations of syntheses and chemistry of spiroheterocycles, we found that reaction of aromatic nitrile oxides with 3-methylenephthalimidines 8 produced spiroheterocycles 9. When N-benzyl-3-methylenephthdimidine (8c) was employed, oximes 10 and 11 were formed in addition to the spiroheterocycles. Solvent effects on the reaction rates and on product ratios indicate that the product mixtures result from competition between a 1, 3- ...