Thiols in Ugi- and Passerini-Smiles-Type Couplings

被引：29

作者：

Barthelon, Anaelle ^{[1
]}

El Kaim, Laurent ^{[1
]}

Gizolme, Marie ^{[1
]}

Grimaud, Laurence ^{[1
]}

机构：

[1] ENSTA, F-75015 Paris, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 35期

关键词：

Ugi reaction; Smiles reaction; Isocyanides; Rearrangement; Thiols; Multicomponent reactions;

D O I：

10.1002/ejoc.200800859

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of the Smiles rearrangement in Ugi-type couplings with aromatic mercaptans allows for the straightforward, multicomponent formation of alpha-arylamino thiocarboxamides. The scope of this new four-component coupling is further broadened with the use of heterocyclic mercapto derivatives that afford thioamides of high biological interest in one step. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

收藏

页码：5974 / 5987

页数：14

相关论文

共 44 条

[1] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[2] Ugi/Smiles access to pyrazine scaffolds [J].

Barthelon, Anaelle ;

Dos Santos, Aurelie ;

El Kaiem, Laurent ;

Grimaud, Laurence .

TETRAHEDRON LETTERS, 2008, 49 (20) :3208-3211

[3] One-pot synthesis of α-acyloxyaminoamides via nitrones as imine surrogates in the Ugi MCR [J].

Basso, A ;

Banfi, L ;

Guanti, G ;

Riva, R .

TETRAHEDRON LETTERS, 2005, 46 (46) :8003-8006

[4]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[5]

2-A

[6] Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction [J].

Bonnaterre, Florence ;

Bois-Choussy, Michele ;

Zhu, Jieping .

ORGANIC LETTERS, 2006, 8 (19) :4351-4354

[7] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

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

Dömling, A .

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

[9]

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

[10]

2-U

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