Three-component synthesis of polysubstituted 6-azaindolines and its tricyclic derivatives

被引：83

作者：

Fayol, A ^{[1
]}

Zhu, JP ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol0477881

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By simply heating a toluene solution of isocyanoacetamide (3), amine (4), and aldehyde (5), a clean three-component reaction occurred to provide the pyrrolidinone-fused azaindoline (2). In this multicomponent reaction, the isocyanoacetamide (3) reacted four times in a highly ordered manner creating three heterocylic rings with the concurrent formation of five chemical bonds and a minimal loss of molecular weight. Heating is the only external energy required to promote this powerful complexity-generating MCR.

引用

页码：239 / 242

页数：4

共 59 条

[1]

ALVAREZ M, 1991, HETEROCYCLES, V32, P1391

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

Balme, G ;

Bossharth, E ;

Monteiro, N .

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

[3]

Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671

[4]

Beller M, 1998, ANGEW CHEM INT EDIT, V37, P3389, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3389::AID-ANIE3389>3.0.CO

[5]

2-D

[6] A versatile synthesis of pyrrolo-, furo- and thienopyridines via photocyclization of 3-amino-2-alkene imines in an acid medium [J].

Campos, PJ ;

Añón, E ;

Malo, MC ;

Rodríguez, MA .

TETRAHEDRON, 1999, 55 (49) :14079-14088

[7] Spectrothermodynamic relationship of cationic vs anionic species derived from protonation vs deprotonation of pyrrolo-aza-aromatic bases in homologous series [J].

Catalán, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) :11940-11944

[8]

CHAMBERS MS, 1996, Patent No. 2295615

[9]

COBURN C, 2000, Patent No. 2000064449

[10] A PRACTICAL SYNTHESIS OF 1H-PYRROLO[2,3-C]PYRIDINE-5-CARBOXYLIC ACID-DERIVATIVES FROM PYRROLE-2-CARBOXALDEHYDES [J].

DEKHANE, M ;

POTIER, P ;

DODD, RH .

TETRAHEDRON, 1993, 49 (36) :8139-8146

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