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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
phrases
Summary
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 +
SEARCH IN
2] cycloaddition reactions. The oxazole ring has found significant use as a precursor to
CHAPTERS
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
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