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

页码：7348 / 7355

页数：8

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