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

Abstract 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[2,3-A]isoindole-6-carboxylic acids. The reaction pro...

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Bibliographic Details
Published in:Synlett 2010-09, Vol.2010 (14), p.2063-2066
Main Authors: Zubkov, Fedor I., Galeev, Timur R., Nikitina, Eugeniya V., Lazenkova, Irina V., Zaytsev, Vladimir P., Varlamov, Alexey V.
Format: Article
Language:English
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Summary:Abstract 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[2,3-A]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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1258513