Phenylglycidyl Ether誘導体の研究 : 第2報 3-置換-3,4-Dihydro-2H-1,4-benzoxazineおよび3-置換-3,4-Dihydro-2H-1,4-benzothiazineの1新合成法

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A new method of synthesizing 3-substituted-3,4-dihydro-2H-1,4 -benzoxazine from o-nitrophenylglycidylether (I) was investigated. The dehydration, with Al_2O_3 or sulfuric acid, of 3-dialkylamino-1-(o-aminophenoxy)-2-propanol (II) which was prepared from I after undergoing amine cleavage and reduction, afforded 3-dialkylamino-3,4-dihydro-2H-1,4-benzoxazine (III) in good yields. III was also synthesized from chlorinated compound of II, 3-dialkylamino-1-(o-aminophenoxy)-2-chloropropane hydrochloride, when it was warmed with dilate alkaline solution. This ring formation can be applied to synthesizing 4-alkyl-3-dialkylaminomethyl-, (or 3-alkoxy-)3,4-dihydro-2H-1,4-benzoxazine from the corresponding phenoxy-propanold erivatives. 3-Substituted-3,4-dihydro-2H-1,4-benzothiazine was also synthesized by the same reaction from 3-dialkylamino-1-(o-aminophenylthio)-2- propanol with a satisfactory yield. 3-Dialkylamino-1-(o-aminophenoxy)-2-propanone obtained from II, when closed, afforded 3-dialkylamino-2H-benzoxazine. This compound, after being hydrogenated, was identified with III.
公益社団法人日本薬学会の論文
1968-09-25