The preparation of resin-bound nitroalkenes and some applications in high pressure promoted cycloadditions

被引：58

作者：

Kuster, GJ ^{[1
]}

Scheeren, HW ^{[1
]}

机构：

[1] Catholic Univ Nijmegen, Dept Organ Chem, NSR Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 04期

关键词：

nitroalkenes; microwave heating; high pressure promoted cycloadditions; solid-phase synthesis;

D O I：

10.1016/S0040-4039(99)02108-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of resin-bound nitroalkenes via a microwave assisted Knoevenagel reaction of resin-bound nitroacetic acid with aryl and alkyl substituted aldehydes is described. The potential of these resin-bound nitroalkenes for application in combinatorial chemistry is demonstrated by a Diels-Alder reaction with 2,3-dimethylbutadiene and one-pot three component tandem [4+2]/[3+2] reactions with ethyl vinyl ether and styrene. The cycloadditions were promoted by high pressure. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：515 / 519

页数：5

共 25 条

[1] HIGH-PRESSURE-PROMOTED (2 + 2) CYCLOADDITIONS OF IMINES WITH ELECTRON-RICH ALKENES - A SIMPLE ROUTE TO AZETIDINES AND BETA-AMINO CARBONYL-COMPOUNDS [J].

ABEN, RWM ;

SMIT, R ;

SCHEEREN, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) :365-370

[2] CHEMOSELECTIVE SYNTHESIS OF FUNCTIONALIZED CONJUGATED NITROALKENES [J].

BALLINI, R ;

CASTAGNANI, R ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2160-2162

[3] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

BARRETT, AGM ;

GRABOSKI, GG .

CHEMICAL REVIEWS, 1986, 86 (05) :751-762

[4] Solid phase synthesis of 2-acyl-3,7,8-substituted-5-oxo-2-azabicyclo[2.2.2]octane and triaza analogs: Resin activation capture approach REACAP technology [J].

Chen, CX ;

Munoz, B .

TETRAHEDRON LETTERS, 1999, 40 (18) :3491-3494

[5]

Craig D, 1998, SYNLETT, P1381

[6] Synthesis of 3,4,5-trisubstituted cyclohexanones by cycloaddition to solid phase 2-aminobutadienes [J].

Crawshaw, M ;

Hird, NW ;

Irie, K ;

Nagai, K .

TETRAHEDRON LETTERS, 1997, 38 (40) :7115-7118

[7] Tandem [4+2]/[3+2] cycloadditions of nitroalkenes [J].

Denmark, SE ;

Thorarensen, A .

CHEMICAL REVIEWS, 1996, 96 (01) :137-165

[8]

GAVINA F, 1979, TETRAHEDRON LETT, V15, P1333

[9] A simple entry towards novel bi- and tricyclic N-oxy-β-lactams by high pressure promoted tandem [4+2]/[3+2] cycloadditions of enol ethers and β-nitrostyrene [J].

Kuster, GJ ;

Kalmoua, F ;

de Gelder, R ;

Scheeren, HW .

CHEMICAL COMMUNICATIONS, 1999, (09) :855-856

[10] High pressure promoted tandem [4+2]/[3+2] cycloadditions on the solid phase [J].

Kuster, GJ ;

Scheeren, HW .

TETRAHEDRON LETTERS, 1998, 39 (21) :3613-3616

← 1 2 3 →