Quinoxaline N-Oxideに関する研究(第4報) : 2-Phenylquinoxaline 4-OxideとGrignard化合物との反応について

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In continuation of the previous work, ^<1)> examinations were made on the reaction between 2-phenylquinoxaline 4-oxide (I) and phenylmagnesium bromide. 1) Heating of I and phenylmagnesium bromide in a mixed solvent of ether and benzene, followed by hydrolysis, and varying the time of heating from 1 to 9 hours, failed to show any distinct relationship between heating time and the ratio of the products, 2,3-dithenylquinoxaline (II) and 2,3-diphenylquinoxaline 1-oxide (III) (Table I). 2) Addition of p-benzoquinone prior to hydrolysis after heating and refluxing I and phenylmagnesium bromide as above, resulted in overwhelming formation of III over II with shortening of the heating period. Amount of III formed decreased with extension of the heating time and, with the same period of heating, addition of p-benzoquinone increased the amount of III formed (Table II). These experimental results indicate that the reaction process can be illustrated as shown in Chart 2,similar to that proposed by Kato and Yamanaka^<7,8)> (Chart 1). Reaction of I with alkylmagnesium halide as the Grignard compound gave results listed in Table III. In this case, when the alkyl was tert-butyl and benzyl, I underwent deoxidation to form 2-phenylquinoxaline (XV), with additional formation of 2-tert-butyl-3-phenyl-1,2-dihydroquinoxaline (XVI) in the cast of tert-butyl. The reaction process in this case may probably be represented as shown in Chart 3.
公益社団法人日本薬学会の論文
1966-07-25

Quinoxaline N-Oxideに関する研究(第4報) : 2-Phenylquinoxaline 4-OxideとGrignard化合物との反応について

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