Studies on the Smiles Rearrangement. XIV. Novel Reactions of 1,3-Dimethyl-5-nitro-6-chlorouracil with 2-Aminothiophenol
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The reaction of 1,3-dimethyl-5-nitro-6-chlorouracil with 2-aminothiophenol in benzene containing an excess of triethylamine gave 1,3-dimethyl-10H-pyrimido (5,4-b) (1,4) benzothiazine-2,4 (1H, 3H) dione quantitatively via the Smiles rearrangement. The reaction in acetic acid, however, resulted in the formation of 2-methyl-4-nitropyrimido (4,3-b) benzothiazoline-1,3 (2H, 10H)-dione in 78% yield, involving an unusual uracil-ring cleavage which appears to occur in a benzothiazoline intermediate in the course of the acid-catalized Smiles rearrangement.
- 公益社団法人日本薬学会の論文
- 1974-06-25
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