Sodium hydride → 3,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
反応式
[H-].[Na+].C(O[CH:6]([O:10]CC)[N:7]([CH3:9])C)C.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[C:29]([CH:31]([C:35]1[CH2:40][CH2:39][CH2:38][C:37](=[O:41])[CH:36]=1)C(N)=O)#[N:30]>>[O:10]=[C:6]1[C:31]([C:29]#[N:30])=[C:35]2[C:36]([C:37](=[O:41])[CH2:38][CH2:39][CH2:40]2)=[CH:9][NH:7]1参加物
実験手順
The novel compounds of the present invention originate from a novel process which utilizes dihydroresorcinol as the starting material. That substance thus is allowed to react with a chlorinating reagent such as phosphorus trichloride to afford 3-chloro-2-cyclohexen-1-one. Reaction with cycnoacetamide and sodium hydride results in α-cyano-3-oxo-1-cyclohexen-1-acetamide, which is contacted with a dialkylformamide acetal, for example dimethylformamide diethyl acetal or dimethylformamide dineopentyl acetal, to produce 2,3,5,6,7,8-hexahydro-3,8-dioxo-4-isoquinolinecarbonitrile. Elimination of the cyano group is effected by heating with hydrobromic acid, thus affording 2,3,5,6,7,8-hexahydro-3,8-isoquinolinedione. Heating with an alkyl or cycloalkyl halide produces the corresponding 6-alkoxy and 6-cycloalkoxy 7-aza-1-tetralones together with the N-alkylated or N-cycloalkylated derivatives. Typically, 2,3,5,6,7,8-hexahydro-3,8-isoquinolinedione is heated in benzene at the reflux temperature with methyl iodide and silver carbonate to yield 7-aza-6-methoxy-1-tetralone together with 2-methyl-2,3,5,6,7,8-hexahydro-3,8-isoquinolinedione.
出典と根拠
- ORDレコード
- ord-395fdc1b6d8544a3b32a986eadf071bb
- 出典データセット
- uspto-grants-1977_03
- 特許番号
- US04012391
反応ノート
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