Straightforward hetero Diels-Alder reactions of nitroso dienophiles by microreactor technology

被引：25

作者：

Monbaliu, Jean-Christophe M. R. ^{[1
]}

Cukalovic, Ana ^{[1
]}

Marchand-Brynaert, Jacqueline ^{[2
]}

Stevens, Christian V. ^{[1
]}

机构：

[1] Univ Ghent, SynBioC Res Grp, Dept Sustainable Organ Chem & Technol, Fac Biosci Engn, B-9000 Ghent, Belgium

[2] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, IMCN, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 44期

基金：

比利时弗兰德研究基金会;

关键词：

Microreactor; Hetero Diels-Alder reaction; Nitroso dienophiles; Flow conditions; C-NITROSOCARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; CYCLOADDITIONS; CYCLOADDUCTS; TRANSIENT; GENERATION; OXIDATION;

D O I：

10.1016/j.tetlet.2010.08.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero Diels-Alder reactions of 2-nitrosotoluene and some representative acylnitrosodienophiles with a selected set of 1,3-dienes were studied under microflow conditions. The main assets of the technology, that is, an accurate control of the reaction parameters and continuous operating, led to an increased efficiency of this reaction. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5830 / 5833

页数：4

共 37 条

[1] Microreactor technology:: Continuous synthesis of 1H-isochromeno[3,4-d]imidazol-5-ones [J].

Acke, Davy R. J. ;

Stevens, Christian V. ;

Roman, Bart I. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2008, 12 (05) :921-928

[2] A HCN-based reaction under microreactor conditions:: industrially feasible and continuous synthesis of 3,4-diamino-1H-isochromen-1-ones [J].

Acke, Davy R. J. ;

Stevens, Christian V. .

GREEN CHEMISTRY, 2007, 9 (04) :386-390

[3] Generation of acylnitroso dienophiles: A study of metal catalysis [J].

Adamo, Mauro F. A. ;

Bruschi, Simone .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2666-2669

[4] Reactions of nitroso hetero-diels-alder cycloadducts with azides: Stereoselective formation of triazolines and aziridines [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10) :3929-3932

[5] Bronsted acid-mediated opening of nitroso cycloadducts under anhydrous conditions [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

TETRAHEDRON LETTERS, 2009, 50 (07) :796-798

[6] α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights [J].

Calvet, Geraldine ;

Coote, Susannah C. ;

Blanchard, Nicolas ;

Kouklovsky, Cyrille .

TETRAHEDRON, 2010, 66 (16) :2969-2980

[7] Syntheses of carbocyclic aminonucleosides and (-)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations [J].

Cesario, Cara ;

Tardibono, Lawrence P., Jr. ;

Miller, Marvin J. .

TETRAHEDRON LETTERS, 2010, 51 (23) :3053-3056

[8] Syntheses of Carbocyclic Uracil Polyoxin C Analogs: Application of Pd(0)/InI-Allylation of 4-Acetoxy-2-azetidinone [J].

Cesario, Cara ;

Miller, Marvin J. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5730-5733

[9] REACTIONS OF TRANSIENT-C-NITROSOCARBONYL COMPOUNDS WITH DIENES, MONOOLEFINS, AND NUCLEOPHILES [J].

CORRIE, JET ;

KIRBY, GW ;

MACKINNON, JWM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04) :883-886

[10] Copper-promoted rearrangement of 1,3-cyclohexadiene-acylnitroso cycloadducts [J].

Crotti, Stefano ;

Bertolini, Ferruccio ;

Macchia, Franco ;

Pineschi, Mauro .

TETRAHEDRON LETTERS, 2010, 51 (17) :2284-2286

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