4-Oxo-1,2,3,4-tetrahydroquinazolines, V. Ring Expansion Reaction of 1-Methyl-3-phenyl-4-oxo-3,4-dihydroquinazolinium Bromide with Diazoalkanes

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概要

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• Reactions of 1-methyl-3-phenyl-4-oxo-3,4-dihydroquinazolinium bromide (<B>13</B>) with diazoalkanes were investigated. Treatment of <B>13</B> with diazomethane in EtOH gave a ring-expansion product <B>14</B> in a good yield. A mechanism which involves the formation of azirinoquinazolinium bromide and a subsequent S<SUB>N</SUB>1 type ring opening was discussed. Treatment of <B>13</B> with phenyldiazomethane also afforded benzodiazepine <B>16</B>. However, reaction of <B>13</B> with ethyldiazoacetate in the presence of CuSO<SUB>4</SUB> gave 4-oxo-1,2,3,4-tetrahydroquinazoline <B>17</B>.

• 公益社団法人 日本化学会の論文

著者

• Yamada Yoshihisa

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• Oine Toyonari

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

• Inoue Ichizo

  Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.

関連論文

• Reaction of 1-Methyl-4-phenylquinazolinium Salts with Diazomethane
• 4-Oxo-1,2,3,4-tetrahydroquinazolines, V. Ring Expansion Reaction of 1-Methyl-3-phenyl-4-oxo-3,4-dihydroquinazolinium Bromide with Diazoalkanes

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