A facile construction of 4-hydroxymethylbenzisothiazolone-1,1-dioxide

doi:10.1016/S0040-4039(98)00011-2

Tetrahedron Letters

Volume 39, Issue 12, 19 March 1998, Pages 1483-1486

https://doi.org/10.1016/S0040-4039(98)00011-2 Get rights and content

Abstract

4-Hydroxymethylbenzisothiazolone-1,1-dioxide could be facilely synthesised via a highly regioselective Diels-Alder cycloaddition between furfuryl alcohol and 2-(tert-butyl)-isothiazolone-1,1-dioxide, followed by aromatization of the adduct under basic conditions. A secondary effect from intramolecular hydrogen bonding is found also to influence the regioselectivity of the cycloaddition. Unequivocal proof of the regiochemistry of the Diels-Alder reaction is provided by X-ray crystallography and ab initio calculations showed electronic and steric effects on transition structure asynchronicity.

4-Hydroxymethylbenzisothiazolone-1,1-dioxide was synthesised via a highly regioselective Diels-Alder cycloaddition.

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A facile construction of 4-hydroxymethylbenzisothiazolone-1,1-dioxide

Abstract

J. Bio. Chem.

Tetrahedron Lett.

J. Med. Chem.

J. Heterocyclic Chem.

J. Med. Chem.

J. Med. Chem.

Drug Development Res.

J. Heterocyclic Chem.

J. Heterocyclic Chem.

J. Med. Chem.

Tetrahedron Lett.

F. Helv. Chim. Acta