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The synthesis of the previously reported thianinhydrin ( 12 ) was achieved from 3-methylthiophene via the corresponding 5,6-dihydrocyclopenta[ b ]thiophen-4,6-dione ( 10 ). Conversion of 10 to the tricarbonyl ( 12 ) proceeded in good yield using dimethydioxirane oxidation of 5,6-dihydro-5-dimethyl aminomethylenecyclopenta[ b ]thiophen-4,6-dione ( 14 ). The fluorescence intensity of the zinc salt of the product of 12 and glycine was similar to that obtained from the product of ninhydrin and the same amino acid. |
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