'On water' direct vinylogous Henry (nitroaldol) reactions of 3,5-dimethyl-4-nitroisoxazole with aldehydes and trifluoromethyl ketones

被引：23

作者：

Zhang, Yong ^{[1
]}

Wei, Biao-Wen ^{[1
]}

Zou, Li-Na ^{[1
]}

Kang, Mei-Lian ^{[1
]}

Luo, Hai-Qing ^{[1
]}

Fan, Xiao-Lin ^{[1
,2
]}

机构：

[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem, Ganzhou 341000, Peoples R China

[2] Pingxiang Univ, Mat & Chem Engn Dept, Pingxiang 337055, Peoples R China

来源：

TETRAHEDRON | 2016年 / 72卷 / 19期

基金：

中国国家自然科学基金;

关键词：

On water; Vinylogous Henry reactions; 4-Nitro-isoxazoles; COLUMN CHROMATOGRAPHY-FREE; DIELS-ALDER REACTIONS; ORGANIC-REACTIONS; ROOM-TEMPERATURE; ALDOL REACTION; CATALYST-FREE; 3-HYDROXY-2-OXINDOLE SCAFFOLDS; MICHAEL REACTIONS; HIGHLY EFFICIENT; CHEMISTRY;

D O I：

10.1016/j.tet.2016.03.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient 'on water'-promoted direct catalytic vinylogous addition of 3,5-dimethyl-4-nitroisoxazole to aldehydes and trifluoromethyl ketones was described, giving Henry (nitroaldol) adducts in excellent yields. The trifluoromethyl tertiary alcohol product could be transformed to the corresponding styrene derivative, which was demonstrated as a new type of Michael acceptor in the vinylogous 1,6-Michael addition with nitromethane. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2472 / 2475

页数：4

共 43 条

[1] Vinylogous nitroaldol (Henry) reaction using 3,5-diethyl-4-nitroisoxazole and carbonyl compounds [J].

Adamo, Mauro F. A. ;

Suresh, Surisetti .

TETRAHEDRON, 2009, 65 (05) :990-997

[2]

[Anonymous], CHEM REV

[3] On-Water Vinylogous Mukaiyama-Michael Addition of Heterocyclic 2-Silyloxydienes to 1,2-Diaza-1,3-dienes: One-Pot Three-Step Entry to Functionality-Rich Pyrroles [J].

Battistini, Lucia ;

Dell'Amico, Luca ;

Sartori, Andrea ;

Curti, Claudio ;

Pelosi, Giorgio ;

Casiraghi, Giovanni ;

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Zanardi, Franca .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1966-1972

[4] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[5] The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress [J].

Casiraghi, Giovanni ;

Battistini, Lucia ;

Curti, Claudio ;

Rassu, Gloria ;

Zanardi, Franca .

CHEMICAL REVIEWS, 2011, 111 (05) :3076-3154

[6] Organic Synthesis "On Water" [J].

Chanda, Arani ;

Fokin, Valery V. .

CHEMICAL REVIEWS, 2009, 109 (02) :725-748

[7] A rational approach towards the nucleophilic substitutions of alcohols "on Water" [J].

Cozzi, Pier Giorgio ;

Zoli, Luca .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4162-4166

[8] "On water"-promoted direct alkynylation of isatins catalyzed by NHC-silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones [J].

Fu, Xiao-Pu ;

Liu, Li ;

Wang, Dong ;

Chen, Yong-Jun ;

Li, Chao-Jun .

GREEN CHEMISTRY, 2011, 13 (03) :549-553

[9] The principle of vinylogy [J].

Fuson, RC .

CHEMICAL REVIEWS, 1935, 16 (01) :1-27

[10] Conjugate Addition versus Cycloaddition/Condensation of Nitro Compounds in Water: Selectivity, Acid-Base Catalysis, and Induction Period [J].

Guideri, Luca ;

De Sarlo, Francesco ;

Machetti, Fabrizio .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (02) :665-677

← 1 2 3 4 5 →