Sequential Ugi/Heck cyclization strategies for the facile construction of highly functionalized N-heterocyclic scaffolds

被引:81
作者
Gracias, V [1 ]
Moore, JD [1 ]
Djuric, SW [1 ]
机构
[1] Abbott Labs, Abbott Pk, IL 60064 USA
关键词
Ugi; Heck; multi-component reaction; solid-phase; scaffold;
D O I
10.1016/j.tetlet.2003.10.147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy employing an Ugi four-component reaction and a microwave-assisted intramolecular Heck cyclization in a sequential fashion to access an array of N-containing heterocycles is reported. The two-step sequence generated compounds of significant molecular complexity from trivial starting materials in an expedient fashion with excellent yields. The route was also amenable to solid-phase chemistry demonstrating potential for library generation. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:417 / 420
页数:4
相关论文
共 36 条
[1]   INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].
ABELMAN, MM ;
OH, T ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133
[2]   Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams [J].
Banfi, L ;
Basso, A ;
Guanti, G ;
Riva, R .
TETRAHEDRON LETTERS, 2003, 44 (41) :7655-7658
[3]   Short and diverse route toward complex natural product-like macrocycles [J].
Beck, B ;
Larbig, G ;
Mejat, B ;
Magnin-Lachaux, M ;
Picard, A ;
Herdtweck, E ;
Dömling, A .
ORGANIC LETTERS, 2003, 5 (07) :1047-1050
[4]   Solid phase synthesis of fused bicyclic amino acid derivatives via intramolecular Pauson-Khand cyclization: Versatile scaffolds for combinatorial chemistry. [J].
Bolton, GL ;
Hodges, JC ;
Rubin, JR .
TETRAHEDRON, 1997, 53 (19) :6611-6634
[5]   Solid-phase synthesis of substituted benzazepines via intramolecular Heck cyclization [J].
Bolton, GL ;
Hodges, JC .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (02) :130-133
[6]   Palladium-catalysed reactions in solid phase organic synthesis [J].
Bräse, S ;
Kirchhoff, JH ;
Köbberling, J .
TETRAHEDRON, 2003, 59 (07) :885-939
[7]   A convenient solution and solid-phase synthesis of Δ5-2-oxopiperazines via N-acyliminium ions cyclization [J].
Cheng, JF ;
Chen, M ;
Arrhenius, T ;
Nadzan, A .
TETRAHEDRON LETTERS, 2002, 43 (36) :6293-6295
[8]   Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNAr-based cycloetherification [J].
Cristau, P ;
Vors, JP ;
Zhu, JP .
TETRAHEDRON LETTERS, 2003, 44 (30) :5575-5578
[9]   Synthesis of chiral 1,1'-iminodicarboxylic acid derivatives from alpha-amino acids, aldehydes, isocyanides, and alcohols by the diastereoselective five-center four-component reaction [J].
Demharter, A ;
Horl, W ;
Herdtweck, E ;
Ugi, I .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02) :173-175
[10]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO