Literature DB >> 16677007

Solution-phase synthesis of a tricyclic pyrrole-2-carboxamide discovery library applying a stetter-Paal-Knorr reaction sequence.

Stefan Werner1, Pravin S Iyer, Matthew D Fodor, Claire M Coleman, Leslie A Twining, Branko Mitasev, Kay M Brummond.   

Abstract

The solution-phase synthesis of a discovery library of 178 tricyclic pyrrole-2-carboxamides was accomplished in nine steps and seven purifications starting with three benzoyl-protected amino acid methyl esters. Further diversity was introduced by two glyoxaldehydes and 41 primary amines. The combination of Pauson-Khand, Stetter, and microwave-assisted Paal-Knorr reactions was applied as a key sequence. The discovery library was designed with the help of QikProp 2.1, and physicochemical data are presented for all pyrroles. Library members were synthesized and purified in parallel and analyzed by LC/MS. Selected compounds were fully characterized.

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Year:  2006        PMID： 16677007      PMCID： PMC3433767          DOI： 10.1021/cc050160c

Source DB:  PubMed          Journal:  J Comb Chem        ISSN： 1520-4766


  33 in total

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