The Chemistry of Heterocyclic Compounds, Oxazoles: Synthesis, Reactions, and Spectroscopy
David C. Palmer
Wiley, Jul 9, 2003 - Science - 640 pages
The Chemistry of Heterocyclic Compounds series attempts to make the extraordinarily complex and diverse field of heterocyclic chemistry as organized and readily accessible as possible, presenting a basic reference collection for practicing researchers. Volume 60, Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A proves the sole comprehensive resource on the synthetic chemistry of oxazoles–heterocyclic compounds containing nitrogen and oxygen, specifically five-membered, unsaturated rings. Oxazoles have a wide variety of applications in synthetic organic chemistry and have been found in numerous natural products such as hennoxazole, thiangazole, calyculin, halicondrins, pyrenolide, virginiamycin, amphotericin, and phorboxazoles. This volume provides an authoritative review of the literature since 1983, highlights compounds of commerical importance, and includes in-depth coverage of the synthesis, reactions, and spectroscopic and physical properties for each class of compounds. It also discusses in detail the exciting developments on the use of chiral bioxazolines in asymmetric synthesis.
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Spectroscopic Properties of Oxazoles
Oxazole DielsAlder Reactions
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1,3-dipolar cycloaddition 1,3-DIPOLAR CYCLOADDITION REACTIONS 2,5-disubstituted Abstr acetic acetic anhydride acid methyl ester acylation addition adduct afforded aldehyde alkyl alkynes amide amino analogs anhydride benzene bis-oxazole BocHN calyculin CDCI3 CH3 CH3 CH3 H CH3CN CH3O CH3OOC Chem chemistry chloride cleavage co-workers compounds converted COOC2H5 COOCH3 coupling cyclization cyclodehydration Data from ref described diastereomers Diels-Alder reaction dienophile dipolarophiles DMAD Entry ester examples are shown Figure fragment furan gave H CH3 H Ph Heterocycl hydrolysis Ibata intermediate intramolecular isolated isomunchnone ketone Lewis acid methodology mixture N-acylamino natural products nitrile nucleophilic OCH3 olefin overall yield oxazole oxazole ring oxazoline oxazolium salt oxidation Padwa Perkin Trans Ph H Ph Ph precursor prepared pyridine pyrroles reacted reaction conditions reactions of oxazoles reagent rearrangement reflux regioisomer regioselective ring opening Selected examples shown in Table steps substituted synthesis Tetrahedron Lett toluene ylide