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
![[img]](http://d-scholarship-dev.library.pitt.edu/style/images/fileicons/text_plain.png) |
Plain Text (licence)
Available under License : See the attached license file.
Download (1kB)
|
Abstract
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.
Share
Citation/Export: |
|
Social Networking: |
|
Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
|
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 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/17356 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Altmetric.com
Actions (login required)
![View Item View Item](/style/images/action_view.png) |
View Item |