| 摘要 |
The invention comprises compounds of the formula <FORM:0817147/IV (b)/1> wherein Py is a 2-pyridyl, alkyl-substituted 2-pyridyl or 4-pyridyl group and R is hydrogen, halogen, hydroxyl, methyl or phenyl, and acid addition and quaternary salts thereof, and their preparation by treating a 1 : 3-benzoxazine 2 : 4-dione (optionally bearing a halogen, hydroxyl, methyl or phenyl substituent) with 2-vinylpyridine, 2-vinyl-5-ethylpyridine or 4-vinylpyridine, preferably at 150-200 DEG C., either with or without a basic catalyst. The products may be converted into their acid addition salts with acids such as hydrochloric, hydrobromic, nitric, phosphoric, sulphuric, lactic, glycollic, citric and tartaric, or into their quaternary salts with esters such as methyl halides, ethyl halides, methyl sulphate and methyl p-toluenesulphonate. Preferred products include 3-[2-(2-pyridyl)-ethyl]-1 : 3-benzoxazine-2 : 4-dione and its 6-chloro-derivative, the 8-methyl- and 7-hydroxy-3-[2-(4-pyridyl)-ethyl] - 1 : 3 - benzoxazine - 2 : 4 - diones and 6 - bromo - 3 - [2 - (5 - ethylpyridyl - (2)) - ethyl] - 1 : 3 - benzoxazine - 2 : 4 - dione. Examples describe the pyridyl-(2), 5-ethylpyridyl - (2) and pyridyl - (4) derivatives of 1 : 3 - benzoxazine - 2 : 4 - dione and its 6-chloro-, 6-bromo-, 8-methyl, 6-phenyl, 8-phenyl, 6-hydroxy and 7-hydroxy derivatives. Benzoxazine-diones substituted in the benzene ring which are used as starting materials such as 6-bromo-, 6-chloro-, 8-methyl-, 6-phenyl-, 8-phenyl-, 6-hydroxy- and 7-hydroxy-1 : 3-benzoxazine-2 : 4-dione are made by converting the corresponding substituted salicylamide into a carbonic acid ester by treatment with ethyl chloroformate (suitable in pyridine-acetonitrile) and cyclizing, with elimination of alcohol. Salicylamides.-5 - Bromo - salicylamide is made by direct bromination. 5-Chloro-, 3-methyl-, 5-phenyl-, 3-phenyl-, 5-hydroxy- and 4-hydroxy-salicylamide are made by esterifying the corresponding salicylic acids with methanol and converting the resulting methyl esters to the amides with ammonia in the presence of aluminium turnings. |
