ISSN:
0947-3440
Keywords:
1H-Pyrroles
;
N-N Bond cleavage
;
a2-Umpolung
;
Nucleophilic substitution
;
2-Acetoxy aldehyde dimethylhydrazones
;
Titanium tetrachloride activation
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Starting from easily available 2-acetoxy aldehyde dimethylhydrazones rac-2, we prepared various alkyl- and aryl-substituted 1H-pyrroles 6 in good overall yield. The titariummediated a2-umpolung reaction of rac-2 with different acyclic and cyclic silyl enol ethers 3 leads directly or via 4-oxo hydrazones rac,anti-4 to 1-(dimethylamino)-1H-pyrroles 5. A novel method for the reductive removal of the dimethylamino group affording 1H-pyrroles 6 is presented.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961011
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