A Simple Preparative Synthesis of Epoxy[1,3]oxazino(or oxazolo)[2,3-a]-isoindoles and Their Thia Analogues via IMDAF

[摘要]：Azomethines, easily prepared from 5-(R)-furfurals and 1,3-or 1,2-amino alcohols (aminothiols), react under mild conditions with maleic anhydride affording 8,10a-epoxy[1,3] oxa(thia)zino[ 2,3-a] isoindole-7-and 7,9a-epoxy[1,3] oxa(thia) zolo[2,3a] isoindole-6-carboxylic acids. The reaction proceeds through initial N-acylation with subsequent intramolecular exo-Diels-Alder cycloaddition and stereoselectively leads to the exo adducts. The ` one-pot' synthetic protocol is also presented.

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