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Parallel Synthesis of Oxazolines and Thiazolines by Tandem Condensation - Cyclodehydration of Carboxylic Acids with Amino Alcohols and Aminothiols

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

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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.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Wang, X
Date: 1 November 2002
Date Type: Publication
Journal or Publication Title: Journal of Combinatorial Chemistry
Volume: 4
Number: 6
Page Range: 656 - 660
DOI or Unique Handle: 10.1021/cc020041m
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1520-4766
MeSH Headings: Amino Alcohols--chemistry; Boronic Acids--chemistry; Carboxylic Acids--chemistry; Combinatorial Chemistry Techniques; Cyclization; Oxazoles--chemical synthesis; Sulfhydryl Compounds--chemistry; Thiazoles--chemical synthesis
PubMed ID: 12425611
Date Deposited: 06 Feb 2014 23:35
Last Modified: 05 Feb 2019 16:55
URI: http://d-scholarship.pitt.edu/id/eprint/20445

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