Ring-Expansion Reaction of Oximes with Aluminum Reductants

被引：23

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

共 16 条

[1] COMPOSITION OF MIXED HYDRIDE REAGENTS . A STUDY OF SCHLESINGER REACTION [J].

ASHBY, EC ;

PRATHER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (04) :729-&

[2] MECHANISM OF MIXED HYDRIDE REDUCTIONS . EFFECTS OF REAGENT COMPOSITION NATURE OF HALOGEN AND SOLVATING LIGAND ON MECHANISM OF EPOXIDE REDUCTION [J].

ASHBY, EC ;

COOKE, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (06) :1625-&

[3] SELECTIVE REDUCTIONS .X. REACTION OF ALUMINUM HYDRIDE WITH SELECTED ORGANIC COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL GROUPS . COMPARISON OF REDUCING CHARACTERISTICS OF LITHIUM ALUMINUM HYDRIDE AND ITS DERIVATIVES [J].

BROWN, HC ;

YOON, NM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (07) :1464-&

[4] Synthesis and structure-activity relationships of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine derivatives:: Novel arginine vasopressin antagonists [J].

Cho, H ;

Murakami, K ;

Nakanishi, H ;

Fujisawa, AK ;

Isoshima, H ;

Niwa, M ;

Hayakawa, K ;

Hase, Y ;

Uchida, I ;

Watanabe, H ;

Wakitani, K ;

Aisaka, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (01) :101-109

[5] Regioselective synthesis of several heterocyclic fused azepines using diisobutylaluminum hydride [J].

Cho, H ;

Murakami, K ;

Nakanishi, H ;

Isoshima, H ;

Hayakawa, K ;

Uchida, I .

HETEROCYCLES, 1998, 48 (05) :919-927

[6] REGIOSPECIFIC REARRANGEMENT OF HYDROXYLAMINES TO SECONDARY AMINES USING DIISOBUTYLALUMINUM HYDRIDE [J].

Cho, Hidetsura ;

Sugimoto, Kenji ;

Iwama, Yusuke ;

Mitsuhashi, Nakako ;

Okano, Kentaro ;

Tokuyama, Hidetoshi .

HETEROCYCLES, 2011, 82 (02) :1633-+

[7] Regioselective Synthesis of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by Reductive Ring Expansion Using Diisobutyl aluminum Hydride and Studies on the Reaction Mechanism [J].

Cho, Hidetsura ;

Iwama, Yusuke ;

Sugimoto, Kenji ;

Mori, Seiji ;

Tokuyama, Hidetoshi .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :627-636

[8] REGIOSPECIFIC SYNTHESIS OF UNSUBSTITUTED BASIC SKELETONS OF HETEROCYCLES CONTAINING NITROGEN NEIGHBORING AN AROMATIC RING BY THE REDUCTIVE RING EXPANSION REACTION USING DIISOBUTYLALUMINUM HYDRIDE [J].

Cho, Hidetsura ;

Iwama, Yusuke ;

Sugimoto, Kenji ;

Kwon, Eunsang ;

Tokuyama, Hidetoshi .

HETEROCYCLES, 2009, 78 (05) :1183-1190

[9]

Orlova E.K., 1975, KHIM GETEROTSIKL, V9, P1262

[10]

ORLOVA EK, 1980, KHIM GETEROTSIKL, V6, P853

← 1 2 →