The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky’s diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4H-1-aminopyrroles and 4,5H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as a matter of fact, the ester or the amide moiety differently affects the acidity of the proton at the adjacent carbon. An unexpected formation of 5H-1-aminopyrroles from the reactions carried out in water was also observed.

Flexible protocol for the chemo- and regioselective building of pyrroles and pyrazoles by reactions of Danishefsky’s dienes with 1,2-diaza-1,3-butadienes

ATTANASI, ORAZIO ANTONIO;FAVI, GIANFRANCO;FILIPPONE, PAOLINO;MANTELLINI, FABIO;MOSCATELLI, GIADA;
2008-01-01

Abstract

The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky’s diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4H-1-aminopyrroles and 4,5H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as a matter of fact, the ester or the amide moiety differently affects the acidity of the proton at the adjacent carbon. An unexpected formation of 5H-1-aminopyrroles from the reactions carried out in water was also observed.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2504294
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