Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation

被引：44

作者：

Neuhaus, James D. ^{[1
]}

Morrow, Sarah M. ^{[1
]}

Brunavs, Michael ^{[2
]}

Willis, Michael C. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

[2] Eli Lilly & Co Ltd, Lily Res Ctr, Sunninghill Rd, Windlesham GU20 6PH, Surrey, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

ARYL METHYL SULFIDES; INTERMOLECULAR HYDROACYLATION; BETA; GAMMA-UNSATURATED KETONES; ALDEHYDES; CYCLIZATION; MECHANISM; METAL; BOND; 2-AMINOBENZALDEHYDES; DERIVATIVES;

D O I：

10.1021/acs.orglett.6b00390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh-catalyzed hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group tolerance, allowing the preparation of diversely substituted quinolines in high yields. Extension to the use of o-alkynyl nitro arenes as substrates leads to 2-nitrochalcones, from which both quinolines and quinoline N-oxides can be accessed.

引用

页码：1562 / 1565

页数：4

共 54 条

[1] Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against Plasmodium falciparum [J].

Andrews, Simeon ;

Burgess, Steven J. ;

Skaalrud, Deborah ;

Kelly, Jane Xu ;

Peyton, David H. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (02) :916-919

[2] Iodine-Mediated Intramolecular Electrophilic Aromatic Cyclization in Allylamines: A General Route to Synthesis of Quinolines, Pyrazolo[4,3-b]pyridines, and Thieno[3,2-b]pyridines [J].

Batchu, Harikrishna ;

Bhattacharyya, Soumya ;

Batra, Sanjay .

ORGANIC LETTERS, 2012, 14 (24) :6330-6333

[3] N-Heterocyclic Carbene (NHC)-Catalyzed Intermolecular Hydroacylation of Cyclopropenes [J].

Bugaut, Xavier ;

Liu, Fan ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8130-8133

[4] 2-Aminobenzaldehydes as Versatile Substrates for Rhodium-Catalyzed Alkyne Hydroacylation: Application to Dihydroquinolone Synthesis [J].

Castaing, Matthias ;

Wason, Sacha L. ;

Estepa, Beatriz ;

Hooper, Joel F. ;

Willis, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) :13280-13283

[5] Intermolecular Hydroacylation: High Activity Rhodium Catalysts Containing Small-Bite-Angle Diphosphine Ligands [J].

Chaplin, Adrian B. ;

Hooper, Joel F. ;

Weller, Andrew S. ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) :4885-4897

[6] Alkyne Hydroacylation: Switching Regioselectivity by Tandem Ruthenium Catalysis [J].

Chen, Qing-An ;

Cruz, Faben A. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) :3157-3160

[7] Regioselective Hydroacylation of 1,3-Dienes by Cobalt Catalysis [J].

Chen, Qing-An ;

Kim, Daniel K. ;

Dong, Vy M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) :3772-3775

[8]

Combes A., 1888, B CHIM SOC FRANCE, V49, P89

[9] On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis [J].

Denmark, SE ;

Venkatraman, S .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1668-1676

[10]

Doebner, 1881, BER DTSCH CHEM GES, V14, P2812, DOI DOI 10.1002/CBER.188101402258

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