Ring-Expansion Reaction of Oximes with Aluminum Reductants

被引：21
|
作者：
Cho, Hidetsura [1 ,2 ]
Iwama, Yusuke [2 ]
Mitsuhashi, Nakako [2 ]
Sugimoto, Kenji [2 ]
Okano, Kentaro [2 ]
Tokuyama, Hidetoshi [2 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
来源：
MOLECULES | 2012年 / 17卷 / 06期
关键词：
aluminum reductant; dichloroaluminum hydride (AlHCl2); ring-expansion of oxime; rearrangement of oxime; cyclopentyl methyl ether (CPME); DIISOBUTYLALUMINUM HYDRIDE; REGIOSELECTIVE SYNTHESIS; AROMATIC RING; REDUCTION; HETEROCYCLES; DERIVATIVES; MECHANISM; REAGENT; SOLVENT;
D O I：
10.3390/molecules17067348
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH((OBu)-Bu-t)(3), and (MeOCH2CH2O)(2)AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.
引用
收藏
页码：7348 / 7355
页数：8
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