Journal
ORGANIC LETTERS
Volume 10, Issue 10, Pages 1983-1986Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol800557h
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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, R-1 = COOR or CONR2 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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