Abstract
BY the action of alkaline potassium hypobromite on phthalamide, Hoogewerff and van Dorp1 obtained 2: 4-dihydroxyquinazoline. Various applications of this intramolecular Hofmann reaction have since been reported; for example, when applied to succinamide, maleamide and pyrazine-2: 3-dicarboxyamide, the reaction leads to dihydro-uracil2, uracil3 and luma-zine4 respectively. We have found that the reaction is applicable to glyoxaline-4: 5-dicarboxyamide (I), which on treatment with alkaline hypobromite solution gives xanthine (II).
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References
Rec. trav. Chim., 10, 4 (1891).
Weidel and Roitner, Monatsh, 17, 174 (1896).
Rinkes, Rec. trav. Ckim., 46, 268 (1927).
Gabriel and Sonn, Ber., 40, 4857 (1907). Cf. Kuhling, Ber., 28, 1968 (1895). Kuhn and Cook, Ber., 70, 761 (1937).
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BAXTER, R., SPRING, F. A New Synthesis of Xanthine. Nature 154, 462–463 (1944). https://doi.org/10.1038/154462b0
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DOI: https://doi.org/10.1038/154462b0
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