eprintid: 22336
rev_number: 21
userid: 1419
dir: disk0/00/02/23/36
datestamp: 2014-07-31 20:49:46
lastmod: 2019-02-03 06:55:04
status_changed: 2014-07-31 20:49:46
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Zaware, N
creators_name: LaPorte, MG
creators_name: Farid, R
creators_name: Liu, L
creators_name: Wipf, P
creators_name: Floreancig, PE
creators_email: 
creators_email: 
creators_email: 
creators_email: 
creators_email: pwipf@pitt.edu
creators_email: 
creators_id: 
creators_id: 
creators_id: 
creators_id: 
creators_id: PWIPF
creators_id: 
title: Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro- 2Hpyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets. © 2011 by the authors.
date: 2011-05-01
date_type: published
publication: Molecules
volume: 16
number: 5
pagerange: 3648 - 3662
refereed: TRUE
id_number: 10.3390/molecules16053648
pmid: 21540794
mesh_headings: Click Chemistry--methods
mesh_headings: Magnetic Resonance Spectroscopy
mesh_headings: Molecular Structure
mesh_headings: Oxidation-Reduction
mesh_headings: Pyrans--chemical synthesis
mesh_headings: Pyrans--chemistry
chemical_names: Pyrans
citation:   Zaware, N and LaPorte, MG and Farid, R and Liu, L and Wipf, P and Floreancig, PE  (2011) Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry.  Molecules, 16 (5).  3648 - 3662.      
document_url: http://d-scholarship-dev.library.pitt.edu/22336/1/molecules-16-03648%281%29.pdf
document_url: http://d-scholarship-dev.library.pitt.edu/22336/8/licence.txt