Chemistry Heterocyclic Building Blocks Oxazoles
A vast class of heterocyclic aromatic organic compounds are derived from the parent compound oxazole, which consists of azoles containing an oxygen and a nitrogen separated by one carbon. While oxazoles are aromatic, they are less so than thiazoles. Oxazole exhibits weak basicity, with its conjugate acid having a pKa value of 0.8, which is lower than the pKa value of 7 for imidazole.
In organic chemistry, there are several classical methods for synthesizing oxazoles. These include the dehydration of 2-acylaminoketones through the Robinson-Gabriel synthesis, the synthesis of oxazoles from cyanohydrins and aldehydes through the Fischer method, the Bredereck reaction that involves α-haloketones and formamide, and the Van Leusen reaction that utilizes aldehydes and TosMIC.
1,3-oxazole is a monocyclic heteroarene that has a five-membered ring structure. It is an analogue of cyclopentadiene where the CH2 at position 1 is replaced with an O and the CH at position 3 is replaced with an N.
Due to their biological activity, including antibacterial, antifungal, antitubercular, anti-inflammatory properties, among others, as well as their usefulness as valuable precursors in various synthetic transformations, oxazole derivatives have generated significant interest in pharmaceutical research and organic synthesis.
The oxazole moiety exhibits a range of biological activities such as anti-inflammatory, antibiotic, antiproliferative, analgesic, antifungal, hypoglycemic, anti-tuberculosis, and muscle relaxant activities.
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(3AS,3a'S,8aR,8a'R)-2,2'-(1-phenylpropane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole)
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2-Bromo-1-(3-methylisoxazol-5-yl)ethanone
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4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride
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(Tetrahydro-1H-oxazolo[3,4-c]oxazol-7a-yl)methanol
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Isoxazol-4-ylmethanamine hydrochloride
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Ethyl 5-chloro-3-methylisoxazole-4-carboxylate
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2-Methyl-2,3-dihydropyrazolo[5,1-b]oxazole
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(4S,4'S)-4,4'-Di-sec-butyl-4,4',5,5'-tetrahydro-2,2'-bioxazole