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Title of article :
4-Chloro-7-nitrobenzofurazan as a Diels–Alder reagent. A facile access to highly functionalized naphthofurazans
Author/Authors :
Vichard، نويسنده , , Dominique and Alvey، نويسنده , , Luke J. and Terrier، نويسنده , , François، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2001
Pages :
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Abstract :
4-Chloro-7-nitrobenzo-2-oxa-1,3-diazole (4-chloro-7-nitrobenzofurazan or NBD chloride) is found to react instantaneously and quantitatively with trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (Danishefskyʹs diene), to form regioselectively the silyl enol ether 4, according to a normal electron-demand Diels–Alder (NEDDA) reaction. This provides the first evidence that this strongly electrophilic heterocycle can also exhibit pericyclic reactivity. Unmasking the enol 4 followed by treatment in the presence of 2 equiv. of base (DBN) leads to 4-chloro-7-hydroxynaphtho[1,2-c]furazan 7. We are thus reporting an easy access to a functionalized hydroxynaphthofurazan, which is obtained under mild conditions in three steps with greater than 80% overall yield.
Keywords :
Benzofurazan , Diels–Alder , naphthofurazan
Journal title :
Tetrahedron Letters
Link To Document :