Three-step solution-phase combinatorial access to 1,2-disubstituted and 1,2,5-trisubstituted pyrroles from carboxylic esters

Hansford, Karl A., Zanzarova, Valeria, Dorr, Aurélie and Lubell, William D. (2004) Three-step solution-phase combinatorial access to 1,2-disubstituted and 1,2,5-trisubstituted pyrroles from carboxylic esters. Journal of Combinatorial Chemistry, 6 6: 893-898. doi:10.1021/cc049904x


Author Hansford, Karl A.
Zanzarova, Valeria
Dorr, Aurélie
Lubell, William D.
Title Three-step solution-phase combinatorial access to 1,2-disubstituted and 1,2,5-trisubstituted pyrroles from carboxylic esters
Journal name Journal of Combinatorial Chemistry   Check publisher's open access policy
ISSN 1520-4766
Publication date 2004-11
Sub-type Article (original research)
DOI 10.1021/cc049904x
Volume 6
Issue 6
Start page 893
End page 898
Total pages 6
Place of publication United States
Publisher American Chemical Society
Language eng
Abstract An efficient diversity-oriented strategy has been developed for the solution-phase parallel synthesis of di-and trisubstituted pyrrole libraries. Methyl esters 1 were effectively converted to 1,2-di- and 1,2,5-trisubstituted pyrroles 5 and 6 in three steps. Treatment of ester 1 with vinylmagnesium bromide in the presence of copper (I) cyanide yielded the corresponding homoallylic ketone 2, which was subjected to ozonolysis or Tsuji-Wacker oxidation to yield the respective cyclization precursors 3 and 4 after aqueous workup. Compounds 3 and 4 were condensed without further purification with a primary amine to afford the desired 1,2-di- or 1,2,5-trisubstituted pyrroles 5 and 6 in good yield and purity.
Keyword Benzenesulfonyl
Antiinflammatory agent
Copper derivative
Ester derivative
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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Created: Fri, 10 Jun 2011, 10:30:50 EST by Susan Allen on behalf of Institute for Molecular Bioscience