Thermolysis of N-Aryl-N-nitrosoureas to Afford Aryl Isocyanates and Nitrosamines via O-Nitrosoisourea Intermediates

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概要

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• Nitrosation of 3,3-dialkyl-1-(4-tolyl)ureas (9) with sodium nitrite in formic acid under ice-cooling gave 3,3-dialkyl-1-(4-tolyl)-1-nitrosoureas (10). In the nitrosation of the ureas with a benzyl group, small amounts of dealkylated nitrosourea, 3-benzyl-1-(4-tolyl)-3-nitrosourea, were formed as a by-product. Decomposition of 10 in CCl_4 at 33℃ under an argon atmosphere gave 4-tolyl isocyanate (11) and N-nitrosodialkylamines (12) besides ureas (9), 3,3-dialkyl-1-(2-nitro-4-tolyl)ureas (13) and 3,3-dialkyl-1-(4-tolyl)triazenes (14). Formation of 11 and 12 suggests the involvement of an O-nitrosoisourea intermediate (15) in the decomposition of 10. In the thermolysis of 10 involving radical decomposition, nitric oxide generated from 10 was trapped as an NO_3 complex of N, N'-etylenebis-(salicylideneiminato)iron (Fe(III)-salen-NO_3).

• 公益社団法人日本薬学会の論文
• 1990-10-25

著者

• 神谷 庄造

  National Institute of Hygienic Sciences, University of Tokyo

• 丹野 雅幸

  National Institute of Hygienic Sciences

• 末吉 祥子

  National Institute of Hygienic Sciences

• 神谷 庄造

  National Institute Of Hygienic Sciences

関連論文

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