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Synthesis of Oxazole Derivatives from Amides and Ketones

The oxazole is formed from the Ugi intermediate, which is ideal to undergo Robinson-Gabriel cyclodehydration with sulfuric acid
Applications
Cyclodehydrating agents
Many cyclodehydrating agents have been discovered to be of use in the Robinson–Gabriel synthesis.

developed a solid-phase synthesis of 1,3-oxazole-based peptides on solid phase from dipeptides by oxidation of the side-chain followed by Wipf and Miller's cyclodehydration of β-ketoamides described above.
Lilly Research Laboratories has disclosed the structure of a described dual PPARα/γ agonist that has possible beneficial impact on type 2 diabetes.

Oxazole synthesis from acid | …
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1,3-Oxazole synthesis - Organic Chemistry Portal

The sequential use of iron and palladium catalysts in an uninterrupted four-step sequence allows the synthesis of trisubstituted isoxazoles from readily available propargylic alcohols
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The initial steps follow the Fischer oxazole synthesis, although the acid-catalyzed cyclization occurs in two steps rather than one, which ensures the formation of the di-chloro intermediate, preventing formation of the regioisomer.
Diarylazoles are common structural motifs in both natural products and drug candidates, however they are difficult to synthesize.

Starting with aspartic acid β esters undergoing acylation to differentiate the first substituent, linked to carbon-2, followed by Dakin-West conversion to keto-amide to introduce the second substituent, and ending with the Robinson-Gabriel cyclodehydration at 90°C for 30 minutes with either phosphorus oxychloride in DMF or catalytic sulfuric acid in acetic anhydride.
Done by:
Su'ad Al-Masri


The Robinson–Gabriel synthesis is an organic reaction in which a 2-acylamino-ketone reacts intramolecularly followed by a dehydration to give an oxazole.

Fischer oxazole synthesis - Wikipedia

Preparation. Classical oxazole synthetic methods in organic chemistry are. the Robinson–Gabriel synthesis by dehydration of 2-acylaminoketones; the Fischer oxazole synthesis from cyanohydrins and aldehydes
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Isoxazole synthesis - Organic Chemistry Portal


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