A novel synthesis of 3‐(hydroxymethyl)chromones from o‐hydroxy‐ω‐(methylsulfinyl)acetophenones has been developed. These have been utilized in the synthesis of 3‐formyl, 3‐cyano, 3‐carboxy, 3‐carboxamido, 3‐chloromethyl, 3‐aminomethyl and 3‐methoxymethylchromones.
A variety of new 3-carbamoyl-4-hydroxy-2//-l,2-benzothiazine 1,1-dioxides of structure II was prepared and evaluated an antiinflammatory agents. Three synthetic methods were employed. Method A, consisting of base-catalyzed carbamoylation of ketone I by isocyanates, and method B, involving aminolysis of j3-keto ester III, are modifications of previously described processes. In the completely new method C, the enamine IV, derived from ketone I, is reacted with phosgene to give the acid chloride V. The latter reacts with an amine to give enamine-amide VI which can be hydrolyzed to II. The prototype compound 2 has the same order of activity as phenylbutazone when evaluated against adjuvant-induced polyarthritis as well as carrageenin-induced edema. Its acute toxicity is less than that of phenylbutazone. The structural modifications described herein all resulted in decreased or complete loss of activity in the carrageenin test.Our continuing studies1 in 1,2-benzothiazine chemistry as
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