Studies on Pyrimidine Derivatives and Related Compounds. LXIII. Reactions of Thiazolium Salts with Dialkyl Acylphosphonates : Takamizawa Reaction 8

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The reactions of diethyl acetyl-and diethyl benzoylphosphonate (2,3) with 3,4-dimethylthiazolium bromide (8) afforded 2-(1-diethylphosphoroyl) ethyl-and 2-(1-diethyl-phosphoroyl) benzyl-3,4-dimethylthiazolium bromides (9,10), which were decomposed to give 2-methyl-and 2-phenyl-4,5-dimethyl-2,3-dihydro-4H-1,4-thiazin-3-ones (11,12) by alkaline treatment. The reactions of 8 with dimethyl acetyl-and dimethyl benzoyl-phosphonate (13,14) gave the inner salts of O-methyl-O-1-(3,4-dimethyl-2-thiazolium)-ethyl-and O-methyl-O-1-(3,4-dimethyl-2-thiazolium) benzyl phosphoric acid (15,16). Similar adducts (18,24) were obtained from the reactions of 1b with 13 and 14. In a careful treatment, the inner salt (26) was found to be produced from 2-(1-diethylphos-phoroyl) ethyl-3-benzyl-4-methyl-5-(2-benzoyloxy) ethylthiazolium bromide (4).
公益社団法人日本薬学会の論文
1969-07-25