A Stereoselective, Base-free, Palladium-Catalyzed Heck Coupling Between 3-halo-1,4-Naphthoquinones and Vinyl-1H-1,2,3-Triazoles

被引：3

作者：

Costa, Dora C. S. ^{[1
]}

Forezi, Luana da S. M. ^{[1
]}

Lessa, Milena D. ^{[1
]}

Delarmelina, Maicon ^{[2
]}

Matuck, Beatriz V. A. ^{[1
]}

Freitas, Maria Clara R. ^{[3
]}

Ferreira, Vitor F. ^{[4
]}

Resende, Jackson A. L. de C. ^{[5
]}

Carneiro, Jose Walkimar de M. ^{[1
]}

da Silva, Fernando de C. ^{[1
]}

机构：

[1] Univ Fed Fluminense, Inst Quim, Campus Valonguinho, BR-24020150 Niteroi, RJ, Brazil

[2] Cardiff Univ, Sch Chem, Main Bldg,Pk Pl, Cardiff CF10 3AT, Wales

[3] Univ Fed Rural Rio de Janeiro, Dept Quim Fundamental & Inorgan, Inst Quim, Campus Seroped, BR-23890000 Seropedica, RJ, Brazil

[4] Univ Fed Fluminense, Fac Farm, Dept Tecnol Farmaceut, BR-24241002 Niteroi, RJ, Brazil

[5] Univ Fed Mato Grosso, Inst Ciencias Exatas & Terra, Campus Univ Araguaia, BR-78698000 Ponta Do Araguaia, MT, Brazil

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 24期

关键词：

Cross-coupling; Heterocycles; Lawsone; Molecular Modeling; Pd(OAc)(2); PEG-400; NAPHTHOQUINONES; 1,2,3-TRIAZOLES; DERIVATIVES; LAPACHONE; AGENTS; CYTOTOXICITY; INHIBITOR; CHEMISTRY;

D O I：

10.1002/slct.202201334

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective, base-free Heck coupling between 1,4-naphthoquinone and 1H-1,2,3-triazole derivatives was reported for the first time. This study shows that depending on the 1,4-naphthoquinone, the use of an additional base is unnecessary to produce the naphthoquinone-triazole conjugates. This is also the first example of a Heck coupling of these two cores without using a base as an additive. In this work, sixteen new naphthoquinone-triazole hybrids were stereoselectively synthetized in good to excellent yields. The reaction mechanism was discussed based on DFT CAM-B3LYP calculations. The first step is the coordination of the arene to the palladium catalyst to form a palladacycle intermediate. After reorganization in this intermediate, the double bond in the arene is restored to proceed with the coupling step and formation of the C-C bond in the rate determining step. The Kozuchi-Shaik span model was employed to rationalize substituent effects.

引用

页数：10

共 41 条

[1] Click Chemistry: 1,2,3-Triazoles as Pharmacophores [J].

Agalave, Sandip G. ;

Maujan, Suleman R. ;

Pore, Vandana S. .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) :2696-2718

[2] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].

Arpad Molnar .

CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320

[3] New 1,2,3,4-tetrahydro-1-aza-anthraquinones and 2-aminoalkyl compounds from norlapachol with molluscicidal activity [J].

Barbosa, TP ;

Camara, CA ;

Silva, TMS ;

Martins, RM ;

Pinto, AC ;

Vargas, MD .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (23) :6464-6469

[4] Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain [J].

Boechat, Nubia ;

Ferreira, Vitor F. ;

Ferreira, Sabrina B. ;

Ferreira, Maria de Lourdes G. ;

da Silva, Fernando de C. ;

Bastos, Monica M. ;

Costa, Marilia dos S. ;

Lourenco, Maria Cristina S. ;

Pinto, Angelo C. ;

Krettli, Antoniana U. ;

Aguiar, Anna Caroline ;

Teixeira, Brunno M. ;

da Silva, Nathalia V. ;

Martins, Priscila R. C. ;

Bezerra, Flavio Augusto F. M. ;

Camilo, Ane Louise S. ;

da Silva, Gerson P. ;

Costa, Carolina C. P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (17) :5988-5999

[5] Molluscicidal activity of 2-hydroxy-[1,4] naphthoquinone and derivatives [J].

Camara, Celso A. ;

Silva, Tania M. S. ;

Da-Silva, Thiago G. ;

Martins, Rodrigo M. ;

Barbosa, Ticiano P. ;

Pinto, Angelo C. ;

Vargas, Maria D. .

ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS, 2008, 80 (02) :329-334

[6] Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives [J].

Carneiro, Paula F. ;

Pinto, Maria C. R. F. ;

Marra, Roberta K. F. ;

da Silva, Fernando de C. ;

Resende, Jackson A. L. C. ;

Rocha e Silva, Luiz F. ;

Alves, Hilkem G. ;

Barbosa, Gleyce S. ;

de Vasconcellos, Marne C. ;

Lima, Emerson S. ;

Pohlit, Adrian M. ;

Ferreira, Vitor F. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 108 :134-140

[7] Synthesis and evaluation of the cytotoxic activity of Furanaphthoquinones tethered to 1H-1,2,3-triazoles in Caco-2, Calu-3, MDA-MB231 cells [J].

Costa, Dora C. S. ;

de Almeida, Gabriella Silva ;

Rabelo, Vitor Won-Held ;

Cabral, Lucio Mendes ;

Sathler, Plinio Cunha ;

Abreu, Paula Alvarez ;

Ferreira, Vitor Francisco ;

Rodrigues Pereira da Silva, Luiz Claudio ;

da Silva, Fernando De C. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 156 :524-533

[8] Naphthoquinoidal [1,2,3]-triazole, a new structural moiety active against Trypanosoma cruzi [J].

da Silva, Eufranio N., Jr. ;

Menna-Barreto, Rubem F. S. ;

Pinto, Maria do Carmo F. R. ;

Silva, Raphael S. F. ;

Teixeira, Daniel V. ;

de Souza, Maria Cecilia B. V. ;

De Simone, Carlos Alberto ;

De Castro, Solange L. ;

Ferreira, Vitor F. ;

Pinto, Antonio V. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (08) :1774-1780

[9] Natural Naphthoquinones with Great Importance in Medicinal Chemistry [J].

da Silva, Fernando de Carvalho ;

Ferreira, Vitor Francisco .

CURRENT ORGANIC SYNTHESIS, 2016, 13 (03) :334-371

[10]

da Silva IF, 2013, MED CHEM, V9, P1085

← 1 2 3 4 5 →