A new synthesis of cyclic ureas, cyclic urethanes, and a quinazolinedione. Selenium-assisted carbonylation of aromatic amines with carbon monoxide.

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概要

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• Five-, six-, and seven-membered cyclic ureas were synthesized in excellent yields from various aromatic diamines by reaction with carbon monoxide and a stoichiometric or excess amount of selenium in the presence of <I>N</I>-methylpyrrolidine. The carbonylation also proceeded using a catalytic amount of selenium in the presence of an oxidizing agent such as oxygen or dimethyl sulfoxide producing selectively the five and six-membered cyclic ureas. In the case of 2-(2-aminoethyl)aniline under the catalytic conditions, intra- and intermolecular carbonylation competed resulting in the formation of a mixture of the seven-membered cyclic urea, 1,3,4,5-tetrahydro-2<I>H</I>-1,3-benzodiazepin-2-one and the acyclic urea, 1,3-bis[2-(2-aminophenyl)ethyl]urea. The distribution ratio of these two products varied depending on the reaction conditions, but selective formation of the cyclic urea was attained only when a stoichiometric or excess amount of selenium was used. In addition to the above diamino compounds, 2-carbamoylaniline, 2-amino-3-pyridinol, and 2-(hydroxymethyl)aniline also underwent similar carbonylation to give 2,4(1<I>H</I>,3<I>H</I>)-quinazolinedione, oxazolo[4,5-<I>b</I>]pyridin-2-(3<I>H</I>)-one, and 1,4-dihydro-2<I>H</I>-3,1-benzoxazin-2-one, respectively.

• 公益社団法人 日本化学会の論文

著者

• Kambe Nobuaki

  Department Of Applied Chemistry And Center For Atomic And Molecular Technologies Graduate School Of

• Murai Shinji

  Department af Chemical Technology Faculty of Engineering Osaka University

• Sonoda Noboru

  Department af Chemical Technology Faculty of Engineering Osaka University

• Yoshida Tohru

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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