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Fluorous parallel synthesis of a piperazinedione-fused tricyclic compound library

Werner, S and Nielsen, SD and Wipf, P and Turner, DM and Chambers, PG and Geib, SJ and Currant, DP and Zhang, W (2009) Fluorous parallel synthesis of a piperazinedione-fused tricyclic compound library. Journal of Combinatorial Chemistry, 11 (3). 452 - 459. ISSN 1520-4766

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A fluorous-linker-assisted solution-phase protocol has been developed and applied to parallel synthesis of a piperazinedione-fused tricyclic compound library. The one-pot [3 + 2] cycloaddition of fluorous amino esters, aldehydes, and maleimides afforded bicyclic proline derivatives. The intermediates were subjected to N-acylation with chloroacetyl chloride, followed by displacement reactions with amines. Linker cleavage with concomitant lactamization yielded the final products. Microwave heating was employed to facilitate several reaction steps and fluorous solid phase extraction (F-SPE) was employed to purify the intermediates. During the method development, a small library containing sixteen analogs was prepared. The optimized conditions were applied to the synthesis of a production library containing ninety analogs. © 2009 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Werner, S
Nielsen, SD
Wipf, Ppwipf@pitt.eduPWIPF
Turner, DM
Chambers, PG
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Currant, DP
Zhang, W
Date: 11 May 2009
Date Type: Publication
Journal or Publication Title: Journal of Combinatorial Chemistry
Volume: 11
Number: 3
Page Range: 452 - 459
DOI or Unique Handle: 10.1021/cc900003q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1520-4766
MeSH Headings: Amines--chemical synthesis; Amines--chemistry; Bicyclo Compounds, Heterocyclic--chemical synthesis; Bicyclo Compounds, Heterocyclic--chemistry; Combinatorial Chemistry Techniques--methods; Cyclization; Esters--chemical synthesis; Esters--chemistry; Fluorine Compounds--chemical synthesis; Fluorine Compounds--chemistry; Maleimides--chemical synthesis; Maleimides--chemistry; Microwaves; Molecular Structure; Piperazines--chemical synthesis; Piperazines--chemistry; Proline--chemical synthesis; Proline--chemistry; Small Molecule Libraries--chemical synthesis; Small Molecule Libraries--chemistry; Solid Phase Extraction--methods
Other ID: NLM NIHMS224873, NLM PMC2921976
PubMed Central ID: PMC2921976
PubMed ID: 19301852
Date Deposited: 21 Feb 2013 22:52
Last Modified: 02 Feb 2019 16:57


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