Ceric ammonium nitrate catalyzed aza-Michael addition of aliphatic amines to α,β-unsaturated carbonyl compounds and nitriles in water

被引：73

作者：

Varala, Ravi ^{[1
]}

Sreelatha, Nuvula ^{[1
]}

Adapa, Srinivas R. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNLETT | 2006年 / 10期

关键词：

ceric ammonium nitrate; aza-Michael reaction; aliphatic amines; alpha; beta-unsaturated carbonyl compounds;

D O I：

10.1055/s-2006-941588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ceric ammonium nitrate (3 mol%) efficiently catalyzes the aza-Michael reaction of amines with alpha,beta-unsaturated carboryl compounds in water to produce the corresponding beta-amino carbonyl compounds in good to excellent yields (55-99%) for most of the compounds under mild conditions. The reaction is procedurally simple and displays limited chemoselectivity, as aromatic amines were found to be unreactive.

引用

页码：1549 / 1553

页数：5

共 41 条

[1] Multiple component reactions:: An efficient nickel-catalyzed reformatsky-type reaction and its application in the parallel synthesis of β-amino carbonyl libraries [J].

Adrian, JC ;

Snapper, ML .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2143-2150

[2]

Alam MM, 2006, LETT ORG CHEM, V3, P187

[3] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].

Alam, MM ;

Varala, R ;

Adapa, SR .

TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119

[4] Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes:: A novel, stereoselective synthesis of α,β-disubstituted β-amino carbonyl compounds via chiral auxiliary mediated azetine formation [J].

Ambhaikar, NB ;

Snyder, JP ;

Liotta, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3690-3691

[5]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[6]

2-E

[7] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

[8] Organic reactions in water: Highly rapid CAN mediated one-pot synthesis of nitriles from aldehydes under mild conditions [J].

Bandgar, BP ;

Makone, SS .

SYNLETT, 2003, (02) :262-264

[9] Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions [J].

Bartoli, G ;

Bartolacci, M ;

Giuliani, A ;

Marcantoni, E ;

Massaccesi, M ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :169-174

[10] Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].

Bartoli, G ;

Bosco, M ;

Marcantoni, E ;

Petrini, M ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055

← 1 2 3 4 5 →