反応式
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2].Cl.[NH2:15]O.[OH-].[Na+]>C(O)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([NH2:15])=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2)([O-:3])=[O:2]参加物
実験手順
In Scheme 13, commercially available 5-nitroisoquinoline is aminated with hydroxylamine hydrochloride and sodium hydroxide in ethanol at 50° C. to yield the 5-nitro-isoquinolin-8-ylamine, which may be diazotized with a mixture of sodium nitrite in a strong acid such as hydrochloric, sulfuric or hydrofluoroboric acid. The diazonium salt may be heated with an appropriate copper salt such a copper chloride, copper bromide or copper cyanide to yield the 8-Cl, 8-Br or 8-CN nitro isoquinolines respectively. The diazonium salt may also be heated in with potassium iodide to yield the 8-iodo intermediate or heated in the presence of an aqueous acid such as sulfuric acid to yield the 8-OH nitroisoquinoline. The tetrafluoroborate diazonium salt may be heated to yield the 8-F nitroisoquinoline. In addition, the diazonium salt may be reacted with a sulfur nucleophile to yield the 8-thioalkyl nitroisoquinoline which may be further oxidized to the 8-sulfoxide or 8-sulfone. Any of the nitroisoquinolines described above may then be reduced by hydrogenation with a suitable catalyst or another suitable reducing agent such as tin(II) chloride and then further elaborated by the chemistry illustrated in Schemes 5 and 6 to the target ureas.
出典と根拠
- ORDレコード
- ord-d416f2f038b049018a0c130552a2cc4b
- 出典データセット
- uspto-grants-2007_02
- 特許番号
- US07183411B2
関連ノート
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