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Studies on as-Triazine Derivatives XIII. A Facile Synthesis of Fusaric Acid from Thienyl-as-triazine Derivatives
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1989
Year
Chemical EngineeringNovel OrganocatalystsDerivativesAs-triazine Derivatives XiiiRetro Diels-alder ReactionEngineeringDerivative (Chemistry)Thienyl-as-triazine DerivativesOrganic ChemistryCatalysisChemistryFusaric AcidPharmacologyChemical DerivativeSynthetic ChemistryRaney NickelNatural Product Synthesis
Reverse electron-demand Diels-Alder reaction of ethyl 6-(2-thienyl)-1,2,4-triazine-3-carboxylate with norbornadiene in boiling p-xylene followed by the elimination of cyclopentadiene (retro Diels-Alder reaction) gave 5-(2-thienyl)pyridine-2-carboxylate. Desulfurization of the thienyl-pyridine with Raney nickel and subsequent saponification afforded fusaric acid (5-butylpyridine-2-carboxylic acid)