Facile synthesis of highly functionalized stable ketenimines via a three-component reaction

被引：16

作者：

Alizadch, Abdolali ^{[1
]}

Rostamnia, Sadegh ^{[1
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

SYNTHESIS-STUTTGART | 2008年 / 01期

关键词：

isocyanides; oximes; ketenimines; multicomponent reactions; zwitterions;

D O I：

10.1055/s-2007-990894

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It is shown that N-alkyl-substituted ketenimine derivatives can be efficiently prepared by the three-component coupling of electron-deficient alkynes, oximes, and isocyanides. The reaction is characterized by mild conditions, high selectivity, and tolerance to various functional groups. Yields are typically around 90%.

引用

收藏

页码：57 / 60

页数：4

相关论文

共 55 条

[1] Amination of pyridylketenes: Experimental and computational studies of strong amide enol stabilization by the 2-pyridyl group [J].

Acton, AW ;

Allen, AD ;

Antunes, LM ;

Fedorov, AV ;

Najafian, K ;

Tidwell, TT ;

Wagner, BD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13790-13794

[2] Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines and imines [J].

Alajarín, M ;

Vidal, A ;

Tovar, F ;

de Arellano, MCR .

TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :489-494

[3] First radical addition onto ketenimines: a novel synthesis of indoles [J].

Alajarin, M ;

Vidal, A ;

Ortin, MM .

TETRAHEDRON LETTERS, 2003, 44 (15) :3027-3030

[4]

ALAJARIN M, 2000, TARGETS HETEROCYCL S, V4, P293

[5]

Alcaide B, 1998, CURR ORG CHEM, V2, P551

[6] C4,C4'-bis-beta-lactam to fused bis-gamma-lactam rearrangement [J].

Alcaide, B ;

MartinCantalejo, Y ;

PerezCastells, J ;

Sierra, MA ;

Monge, A .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9156-9163

[7] Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids:: an efficient method for the synthesis of dialkyl (E)-2{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives [J].

Alizadeh, Abdolah ;

Rostamnia, Sadegh ;

Zhu, Long-Guan .

TETRAHEDRON, 2006, 62 (24) :5641-5644

[8] Synthesis of nicotinamide and isonicotinamide derivatives via multicomponent reaction of alkyl isocyanides and acetylenic compounds in the presence of nicotinic or isonicotinic acid [J].

Alizadeh, Abdolali ;

Oskueyan, Qasem ;

Rostamnia, Sadegh .

SYNTHESIS-STUTTGART, 2007, (17) :2637-2640

[9] A novel synthesis of aminofurans using a four-component reaction [J].

Alizadeh, Abdolali ;

Rostamnia, Sadegh ;

Zoreh, Nasrin ;

Oskueyan, Qasem .

SYNLETT, 2007, (10) :1610-1612

[10] Synthesis of functionalized sulfonamides via multicomponent reaction of alkyl isocyanide and dialkyl acetylenedicarboxylate with 4-methylbenzenesulfonic acid monohydrate [J].

Alizadeh, Abdolali ;

Rostamnia, Sadegh ;

Esmaili, Abbas Ali .

SYNTHESIS-STUTTGART, 2007, (05) :709-712

← 1 2 3 4 5 6 →