The monotosylates obtained by treatment of α- and β- cyclodextrin with p- methylbenzenesulfonyl chloride reacted with ammonia to give the title compounds. These amines are of unusually low basicity , with pKa values of 8.70 and 8.72, respectively. In water at 25°, the hydrochloride salt of the amine derived from β- cyclodextrin is approximately 40 times more soluble than β-cyclodextrin and, through complexation, the salt increases the solubility of Nabumetone over 800 times.

Ethyl 5-oxo-2,5-dihydroisoxazole-4-carboxylate has been treated with a number of chlorinated heterocycles to yield the corresponding substitution products: ethyl 2-(isoquinolin-1-yl)-5-oxo-2,5-dihydroisoxazole-4-carboxylate, ethyl 5-oxo-2-(quinolin-2-yl)-2,5- dihydroisoxazole-4-carboxylate, ethyl 5-oxo-2-(purin-2-yl)-2,5- dihydroisoxazole-4-carboxylate, ethyl 5-oxo-2-(pyrimidin-2-yl)-2,5-dihydroisoxazole-4-carboxylate, ethyl 2-(6-chlorpyridazin-3-yl)-5-oxo- 2,5-dihydroisoxazole-4-carboxylate, ethyl 2-(benzothiazol-2-yl)-5-oxo- 2,5-dihydroisoxazole-4-carboxylate, 2- and 6-(4-ethoxycarbonyl-5-oxo-2,5-dihydroisoxazol-2-yl)pyridine-3-carboxylic acid, ethyl 5-oxo- 2-(2-phenylquinazolin-4-yl)-2,5-dihydroisoxazole-4-carboxylate and ethyl 2-(2,4-diaminotriazin-2-yl)-5-oxo-2,5-dihydroisoxazole-4- carboxylate . The compounds generally cause loss of motor control in mice, but are relatively toxic.

The rearrangement of a number of ethyl 2-(heterocyclic)-5-oxo-2,5-dihydroisoxazole-4-carb-oxylates by mild base is described, leading to new syntheses of the pyrimido [2,1-a] isoquinoline, pyrimido [1,2-a]quinoline, pyrimido [2,1-b] benzothiazole , pyrirnido [1,2-a] pyrimidine, pyrimido [1,2-b]pyridazine and pyrimido [1,2-c] quinazoline ring systems. A mechanism is suggested, and X-ray crystallographic evidence presented for the structure of one of the products, ethyl 2-hydroxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate.

The isomeric 3-[hydroxy(phenyl)methyl]isobenzofuran-1(3H)-ones, of known configuration, have been converted into the corresponding amino and dimethylamino compounds with inversion of configuration, and hence the stereochemistry of these compounds has been determined. The amino compounds have been converted into the corresponding 3-aryl-4-hydroxy-3,4-dihydroisoquinolin-l(2H)-ones, confirming their stereochemical assignments. Attempted displacement of the tosyloxy group in the isomeric 3-[phenyl(toluenesulfonyloxy)methyl]isobenzofuran-l(3H)-ones with dimethylamine proceeded by rearrangement to an epoxy amide and a keto amide.

Potassium phthalide-3-carboxylate (3-oxo-1,3-dihydroisobenzofuran-1- carboxylate ) decarboxylates readily in dimethyl sulfoxide at 145°, and the intermediate phthalidyl anion is efficiently trapped by α,β - unsaturated ketones. The major 1,4-addition product is accompanied by smaller amounts of an isomeric product formed by subsequent cyclization and rearrangement, and sometimes traces of a 1 : 2 1,4-addition product. The caesium salt gives slightly more cyclized product, and the lithium salt undergoes very slow decarboxylation. The synthetic usefulness of the salt decarboxylation is compared with that of the free acid.