Synthesis of α-isocyano-α-alkyl(aryl)acetamides and their use in the multicomponent synthesis of 5-aminooxazole, pyrrolo[3,4-b]pyridin-5-one and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine

被引：40

作者：

Fayol, A ^{[1
]}

Housseman, C ^{[1
]}

Sun, XW ^{[1
]}

Janvier, P ^{[1
]}

Bienaymé, H ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

SYNTHESIS-STUTTGART | 2005年 / 01期

关键词：

domino process; multicomponent reaction; heterocycles; isonitrile; oxazole; pyrrolopyridinone; tetrahydrofuropyridine;

D O I：

10.1055/s-2004-831225

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Isocyano-beta-phenylpropionamide 1 is synthesized from the corresponding amino acid in excellent yield. The unique reactivity of this bifunctional compound is exploited for the development of novel multicomponent synthesis of 5-aminooxazole 6, pyrrolo[3,4-b]pyridin-5-one 10 and 4.5,6,7-tetrahydrofuro[2,3-c]pyridine 13.

引用

页码：161 / 165

页数：5

共 35 条

[1] Pd-assisted multicomponent synthesis of heterocycles [J].

Balme, G ;

Bossharth, E ;

Monteiro, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111

[2] Novel multicomponent reaction for the combinatorial synthesis of 2-imidazolines [J].

Bon, RS ;

Hong, CG ;

Bouma, MJ ;

Schmitz, RF ;

de Kanter, FJJ ;

Lutz, M ;

Spek, AL ;

Orru, RVA .

ORGANIC LETTERS, 2003, 5 (20) :3759-3762

[3] Recent advances in isocyanide-based multicomponent chemistry [J].

Dömling, A .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) :306-313

[4]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[5]

2-U

[6] Synthesis of polysubstituted 4,5,6,7-tetrahydrofuro[2,3-c]pyridines by a novel multicomponent reaction [J].

Fayol, A ;

Zhu, JP .

ORGANIC LETTERS, 2004, 6 (01) :115-118

[7]

Fayol A, 2002, ANGEW CHEM INT EDIT, V41, P3633, DOI 10.1002/1521-3773(20021004)41:19<3633::AID-ANIE3633>3.0.CO

[8]

2-T

[9] Multicomponent domino process to oxa-bridged polyheterocycles and pyrrolopyridines, structural diversity derived from work-up procedure [J].

Gámez-Montaño, R ;

González-Zamora, E ;

Potier, P ;

Zhu, JP .

TETRAHEDRON, 2002, 58 (32) :6351-6358

[10]

Gamez-Montano R., 2002, J CHEM SOC CHEM COMM, P2448

← 1 2 3 4 →