Reaction of 1-Methyl-4-phenylquinazolinium Salts with Diazomethane

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概要

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• For the synthesis of 5-phenyl-1,4-benzodiazepines, reaction of quinazolinium salts with diazomethane was studied. In the course of the study, it was found by NMR spectroscopy that the starting materials (<B>2</B>) reacted even with a slight amount of water present in the solvent to give hydrates <B>5</B>. Treatment of <B>2c</B> with diazomethane at 10 °C under absolute anhydrous conditions gave quinazoline <B>8c</B> and benzodiazepines <B>9</B> and <B>10c</B> in about the same ratio. In the reactions at lower temperatures, the distribution of the products varied markedly, and the ring expansion product <B>10c</B> was obtained in an improved yield. The mechanism for the formation of <B>8</B>, <B>9</B>, and <B>10</B> was discussed.

• 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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