Metal-free C(sp3)-H oxidation of 2-methylquinolines with PIDA under microwave irradiation

被引：12

作者：

Jiang, Long ^{[1
,2
]}

Huang, Yingyi ^{[1
]}

Yan, Yiyan ^{[2
]}

Xie, Yuanyuan ^{[1
,2
]}

机构：

[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou, Zhejiang, Peoples R China

[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 37期

基金：

中国国家自然科学基金;

关键词：

Oxidation; 2-Methylquinolines; PIDA; Microwave; H2O; BASES;

D O I：

10.1016/j.tetlet.2016.07.107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient metal-free protocol has been developed for the sp(3) C-H bond oxidation of 2-methylquinolines in the presence of PIDA under microwave irradiation, providing 2-quinolinecarboxaldehydes with moderate to high yields and excellent selectivities. A wide range of 2-quinolinecarboxaldehydes with different functional groups have been synthesized. A tentative mechanism has been presented to explain this highly selective oxidation process. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：4149 / 4151

页数：3

共 14 条

[1] Solvent free synthesis and deprotection of 1,1-diacetates over a commercially available zeolite Y as a reusable catalyst [J].

Ballini, R ;

Bordoni, M ;

Bosica, G ;

Maggi, R ;

Sartori, G .

TETRAHEDRON LETTERS, 1998, 39 (41) :7587-7590

[2] Petroleum bases I Reactions of 2,3,8-trimethylquinoline [J].

Burger, A ;

Modlin, LR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1079-1083

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

Chanda, Arani ;

Fokin, Valery V. .

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

[4]

Derong D., 2013, TETRAHEDRON LETT, V54, P5211

[5] Synthesis and biological evaluation of substituted quinolines:: Potential treatment of protozoal and retroviral co-infections [J].

Fakhfakh, MA ;

Fournet, A ;

Prina, E ;

Mouscadet, JF ;

Franck, X ;

Hocquemiller, R ;

Figadère, B .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :5013-5023

[6] A GENERAL, SELECTIVE, AND CONVENIENT PROCEDURE OF HOMOLYTIC FORMYLATION OF HETEROAROMATIC BASES [J].

GIORDANO, C ;

MINISCI, F ;

VISMARA, E ;

LEVI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :536-537

[7] 2-Quinolinecarboxaldehyde: Polymorphic behavior of a small rigid molecule [J].

Maria, Teresa M. R. ;

Eusebio, M. Ermelinda S. ;

Almeida e Silva, J. ;

Sobral, Abilio J. F. N. ;

Cardoso, C. ;

Paixao, J. A. ;

Ramos Silva, M. .

JOURNAL OF MOLECULAR STRUCTURE, 2012, 1030 :67-+

[8] Synthesis, anticonvulsant and antihypertensive activities of 8-substituted quinoline derivatives [J].

Muruganantham, N ;

Sivakumar, R ;

Anbalagan, N ;

Gunasekaran, V ;

Leonard, JT .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2004, 27 (10) :1683-1687

[9] New and Practical Synthesis of Montelukast Sodium, an Antiasthmatic Drug [J].

Saravanan, M. ;

Satyanarayana, B. ;

Reddy, P. Pratap .

SYNTHETIC COMMUNICATIONS, 2013, 43 (15) :2050-2056

[10] Novel Conjugated Quinoline-Indoles Compromise Plasmodium falciparum Mitochondrial Function and Show Promising Antimalarial Activity [J].

Teguh, Silvia C. ;

Klonis, Nectarios ;

Duffy, Sandra ;

Lucantoni, Leonardo ;

Avery, Vicky M. ;

Hutton, Craig A. ;

Baell, Jonathan B. ;

Tilley, Leann .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (15) :6200-6215

← 1 2 →