eprintid: 20445
rev_number: 16
userid: 1419
dir: disk0/00/02/04/45
datestamp: 2014-02-06 23:35:43
lastmod: 2019-02-05 16:55:09
status_changed: 2014-02-06 23:35:43
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Wipf, P
creators_name: Wang, X
creators_email: pwipf@pitt.edu
creators_email: 
creators_id: PWIPF
creators_id: 
title: Parallel Synthesis of Oxazolines and Thiazolines by Tandem Condensation - Cyclodehydration of Carboxylic Acids with Amino Alcohols and Aminothiols
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: A combinatorial library of oxazolines and thiazolines was synthesized in moderate to excellent yields using a newly developed methodology. Free carboxylic acids were directly condensed with amino alcohols and aminothiols in the presence of 3-nitrophenylboronic acid as a dehydration catalyst. The library synthesis illustrates the scope of this process: After traditional reaction optimization, a total of 17 oxazolines and 6 thiazolines were successfully prepared in a 24-reaction setup in a Radleys GreenHouse parallel synthesizer. The yields of the parallel reactions ranged from moderate to excellent, depending largely on carboxylate reactivity and functionalization, and generally exceeded those of the traditional reaction setup. The target compounds were isolated in high purities (average purity is 96% according to GC analysis) after passing reaction mixtures through short PrepSep SPE Florisil cartridges.
date: 2002-11-01
date_type: published
publication: Journal of Combinatorial Chemistry
volume: 4
number: 6
pagerange: 656 - 660
refereed: TRUE
issn: 1520-4766
id_number: 10.1021/cc020041m
pmid: 12425611
mesh_headings: Amino Alcohols--chemistry
mesh_headings: Boronic Acids--chemistry
mesh_headings: Carboxylic Acids--chemistry
mesh_headings: Combinatorial Chemistry Techniques
mesh_headings: Cyclization
mesh_headings: Oxazoles--chemical synthesis
mesh_headings: Sulfhydryl Compounds--chemistry
mesh_headings: Thiazoles--chemical synthesis
chemical_names: Amino Alcohols
chemical_names: Boronic Acids
chemical_names: Carboxylic Acids
chemical_names: Oxazoles
chemical_names: Sulfhydryl Compounds
chemical_names: Thiazoles
chemical_names: 3-nitrobenzeneboronic acid
citation:   Wipf, P and Wang, X  (2002) Parallel Synthesis of Oxazolines and Thiazolines by Tandem Condensation - Cyclodehydration of Carboxylic Acids with Amino Alcohols and Aminothiols.  Journal of Combinatorial Chemistry, 4 (6).  656 - 660.  ISSN 1520-4766     
document_url: http://d-scholarship-dev.library.pitt.edu/20445/1/licence.txt