Nano copper oxide mediated ligand-free C-S cross-coupling and concomitant oxidative aromatization of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts

被引：21

作者：

Bhong, Bhagyashree Y. ^{[1
]}

Shelke, Amol V. ^{[1
]}

Karade, Nandkishor N. ^{[1
]}

机构：

[1] Rashtrasant Tukadoji Maharaj Nagpur Univ, Dept Chem, Nagpur 440033, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 08期

关键词：

Nanoparticles; Biginelli reaction; C-S cross-coupling; Diaryliodonium salts; Oxidative aromatization; ARYL HALIDES; CATALYZED SYNTHESIS; EFFICIENT; THIOLS; POTENT; DIHYDROPYRIMIDINES; DERIVATIVES; INHIBITORS; CHEMISTRY; ARYLATION;

D O I：

10.1016/j.tetlet.2012.10.131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of Biginelli 4-aryl-3,4-dihydropyrimidin-2(1H)-thiones undergo ligand-free C-S cross-coupling with diaryliodonium triflates in the presence of CuO nanoparticles with the concomitant oxidative aromatization to form highly substituted 2-(thioaryl)pyrimidine. The nano CuO catalyst can be recycled and reused three times without any significant loss of catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：739 / 743

页数：5

共 49 条

[1]

AKHTAR MS, 1987, INDIAN J CHEM B, V26, P556

[2] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS - 2-HETEROSUBSTITUTED 4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

SCHWARTZ, J ;

MORELAND, S ;

HEDBERG, A ;

GOUGOUTAS, JZ ;

MALLEY, MF ;

FLOYD, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1510-1515

[3] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[4] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[5] Iron-catalyzed S-arylation of thiols with aryl iodides [J].

Correa, Arkaitz ;

Carril, Monica ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2880-2883

[6] Creating chemical diversity space by scaffold decoration of dihydropyrimidines [J].

Dallinger, D ;

Kappe, CO .

PURE AND APPLIED CHEMISTRY, 2005, 77 (01) :155-161

[7] New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies [J].

De Martino, G ;

Edler, MC ;

La Regina, G ;

Coluccia, A ;

Barbera, MC ;

Barrow, D ;

Nicholson, RI ;

Chiosis, G ;

Brancale, A ;

Hamel, E ;

Artico, M ;

Silvestri, R .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) :947-954

[8] A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].

Fernández-Rodríguez, MA ;

Shen, QL ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181

[9] Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols [J].

Fernandez-Rodriguez, Manuel A. ;

Shen, Qilong ;

Hartwig, John F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) :7782-7796

[10]

Harsha Vardhan Reddy K., 2012, TETRAHEDRON LETT, V53, P3061

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