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Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A,

Volume 60
Series: The Chemistry of Heterocyclic Compounds
Published Online: 11 Aug 2003 1
Editor(s): David C. Palmer
Series Editor(s): Edward C. Taylor, Peter Wipf, Arnold Weissberger
Print ISBN: 9780471394945 Online ISBN: 9780471428039 quicksearch
Copyright © 2003 John Wiley & Sons, Inc.

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Synthesis and Reactions of Oxazoles Title
Chapter Authors: David C. Palmer, Srikanth Venkatraman
Series: The Chemistry of Heterocyclic Compounds Enter words or
The chemistry of oxazoles continues to be an important focus of academic and industrial
laboratories around the world. This small-ring heterocycle has elicited extraordinary
creativity from medicinal and process chemists, polymer chemists, materials scientists,
photographic dye chemists, and natural products chemists engaged in basic and applied • Advanced
research. Search
Synthetic strategies for almost any oxazole-substitution pattern are available from classical
methods or have been developed as new methodologies. Oxazoles are readily prepared
• CrossRef /
from cyclic precursors such as oxazolines, N-acyltriazoles, N-acylaziridines, isoxazoles, N- Google
acylisoxazolones, and imidazoles. On the other hand, virtually any type of functionalized Search

acyclic moiety has been converted to an oxazole. For example, -diazoketones, -esters,
• Acronym
-nitriles, -sulfones, and -phosphonates have been converted to oxazoles using rhodium- Finder
carbene methodology. Acetylenes, acyl cyanides, amides, amino acids, amino nitriles,
azides, enamines, hydrazones, imidates, imines, isocyanides, ketones, oximes, nitriles, quicksearch
thioimidates, and vinyl halides are all useful precursors to oxazoles. Oxazoles are now
routinely prepared very efficiently via solid-phase methodologies that have been adapted for
combinatorial libraries and parallel syntheses. book
Oxazoles serve as versatile precursors to a remarkable variety of heterocyclic ring systems
via nucleophilic addition, ring opening, and recyclization as well as [2 + 2], [3 + 2], and [4 +
2] cycloaddition reactions. The oxazole ring has found significant use as a precursor to
aminoketones, amino acids, dipeptides, and triacylamines. The predictable and
regioselective metallation chemistry of oxazoles has been combined with transition metal- Enter words or
catalyzed cross-coupling reactions to provide synthetic approaches to a vast array of phrases
increasingly complex natural products. In addition, the complexity and sensitivity of oxazole
natural products, particularly those of marine origin, has fostered several novel, efficient,
and mild syntheses of mono-, bis-, and tris-oxazoles. Oxazoles have served as scaffolds
from which macrocyclization reactions have produced a variety of interesting and novel Select a Field
depsipeptides and macrolactones. Despite these significant advances, challenges remain.
For example, a mild, efficient, and general method to oxidize 4-alkyloxazolines to 4- All Fields
alkyloxazoles is still needed.
The chapter describes the major developments in this field from 1983 to 2001. isbn

The chapter is divided into the following sections: Introduction, Synthesis of Oxazoles, 9780471428039

Reactions of Oxazoles, and Oxazole Natural Products. The introduction is a brief

discussion of the numbering and lists the major 1H, 13C, and 15N resonances of a few <a href="/index.h
selected examples.
The second section describes the common methods of synthesis. No attempt has been
made to describe every monocyclic oxazole synthesized of all synthetic methods. The most
common and useful synthetic methods and some particularly novel methods have been
included together with tables of some representative examples. In addition, this section and
the reactions of oxazoles are not necessarily organized in the same manner as in the
previous volume. This reflects the changing emphasis on new methods applicable to
complex natural product synthesis.
The third section presents important reactions of oxazoles but again no attempt has been Now available
made to describe every reaction of an oxazole or every derivative prepared. There, the aim online...
is to convey the wealth of chemistry available by the selected examples. Encyclopedia of
The last section includes syntheses of some naturally occurring oxazoles. The choice of Inorganic
these natural products is arbitrary and selected from the recent literature to demonstrate the Chemistry, 2e
versatility of oxazoles in synthesis.
KEYWORDS Editor-in-Chief R. Bruce King
oxazoles; synthesis; reactions; oxidation; oxazolines; nickel peroxide; manganese dioxide; The ultimate resource on
copper salts; Kharasch-Sosnovsky reaction; rearrangements; N-acylaziridines; N- inorganic chemistry – new and
acyltriazoles; isoxazoles; N-acylisoxazolones; rhodium carbene; additions; organotellurium completely revised
reagents; organomercury reagents; substituted ketones; cyclizations; propargylic amides;
Find out more
azides; vinylogous amides; enamino esters; imidates; thioimidates; cornforth reaction;
isocyanides; vinyl bromides; alpha-acyloxyketones; Robinson-Gabriel reaction; electrophilic
reactions; nucleophilic reactions; hydrolysis; reduction; cycloaddition; heterocycles; cross-
coupling; trimethylsilyloxazoles; Wittig reagents; thiangazole; tautazole; calyculins;
hennoxazoles; diazonamides; ulapulides; natural products; organometallic reactions;
stretogramin antibiotics; oxazolium salts; transition metal catalyst; oximes; hydrazones
10.1002/0471428035.ch1 About DOI
David C. Palmer, Srikanth Venkatraman
Schering-Plough Research Institute, Kenilworth, New Jersey, USA

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