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Original Articles

Synthesis of Dialkyl 8-Oxo-2,8-dihydroisoxazolo[3,2-a]isoindole-2,3-dicarboxylates from Dialkyl Acetylenedicarboxylates, N-Hydroxy Phthalimide and Tributylphosphine

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Pages 2523-2527 | Received 09 Apr 2007, Accepted 04 May 2007, Published online: 25 Sep 2007
 

Abstract

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between tributylphosphine and dialkyl acetylenedicarboxylates by N-hydroxy phthalimide leads to vinyltributylphosphonium salts, which undergo electrophilic substitution reaction with conjugate base to produce corresponding stabilized phosphorus ylides. Microwave was found to catalyze conversion of the stabilized phosphorus ylides to dialkyl 8-oxo-2,8-dihydroisoxazolo[3,2-a]isoindole-2,3-dicarboxylates in the presence of solid catalysts in solvent-free conditions.

Acknowledgments

The Zanjan University and Sandoogh Hemayate as Pajuoheshgharane Keshvare Iran supported this work.

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