The reaction of methyl 3-arylamino-2-benzoylaminopropenoates 2 with phosphorus oxychloride in pyridinc at 70°C for 30 min leads to the unexpected formation of N-aryl-N-bis-(5-oxo-2-phenyl-4, 5dihydro-oxazol4-ylmethylene) amines 4. In contrast, 4-arylaminomethylene-2-phenyl-2-oxazolin-5-ones 3 are obtaincd in only 2 min from compounds 2 under similar reaction conditions, which subsequently give compounds 4 on treatmcnt with POCI) in pyridine. A tentative mechanism to account the following conversion is suggcsted .

Methyl 3-arylamino-2-benzoylaminopropenoates react with phosphorus oxychloride in pyridine for 30 minutes, forming unexpected bis-oxazolones, while 4-arylaminomethylene-2-phenyl-2-oxazolin

ChemInform

Methyl 3-Arylamino-2-benzoylaminopropenoates in the Synthesis of 4-Arylaminomethylene-2-phenyl-2-oxazolin-5-ones: Unexpected Formation of Bis-oxazolones.

Paper

Methyl 3-Arylamino-2-benzoylaminopropenoates in the Synthesis of 4-Arylaminomethylene-2-phenyl-2-oxazolin-5-ones: Unexpected Formation of Bis-oxazolones.

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