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Mn(III)-Based O
Heterocycles ( IF 0.6 ) Pub Date : 2020-10-20 , DOI: 10.3987/com-20-s(k)31
Hiroshi Nishino , Takayuki Nagashimada , Masahiro Morikawa , Kengo Ohki

The synthesis of quinolines from aniline derivatives via the Mn(III)-based oxidative cyclization of 2-(2-(arylamino)ethyl)malonates is described. The 2-(2-(arylamino)ethyl)malonates were prepared in two steps from the substituted anilines. The cyclization of nineteen arylaminoethylmalonates protected by the N-acyl and N-alkoxycarbonyl groups easily proceeded in the formal 6-endo mode regardless of the presence of halo, methyl, and methoxy groups on the aromatic ring, and the corresponding tetrahydroquinolinedicarboxylates were produced in high yields except for the 2,4-dimethoxyphenyl-substituted aminoethylmalonate which occurred by ipso-cyclization. The tetrahydroquinolinedicarboxylate could be transformed into quinoline via decarboxylation and deprotective hydrolysis. The characteristic phenomenon in the NMR spectrum of the tetrahydroquinolinedicarboxylates is also discussed.

中文翻译:

Mn(III)基的O

描述了通过2-(2-(芳基氨基)乙基)丙二酸酯的基于Mn(III)的氧化环化反应由苯胺衍生物合成喹啉。由取代的苯胺分两步制备2-(2-(芳基氨基)乙基)丙二酸酯。由保护19个arylaminoethylmalonates环化Ñ酰基和Ñ在正规6-容易进行烷氧基羰基基团无论卤素,甲基,和芳环上的甲氧基,的存在的模式和对应的tetrahydroquinolinedicarboxylates是在高生产产生2,4-二甲氧基苯基取代的氨基乙基丙二酸酯ipso产生 -环化。可以通过脱羧和脱保护水解将四氢喹啉二羧酸酯转化为喹啉。还讨论了四氢喹啉二羧酸酯的NMR光谱中的特征现象。
更新日期:2020-12-17
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