Synthesis of Dibenzodiazepinones via Tandem Copper(I)-Catalyzed C-N Bond Formation

被引：21

作者：

Gawande, Sachin D. ^{[1
]}

Kavala, Veerababurao ^{[1
]}

Zanwar, Manoj R. ^{[1
]}

Kuo, Chun-Wei ^{[1
]}

Huang, Wen-Chang ^{[1
]}

Kuo, Ting-Shen ^{[1
]}

Huang, Hsiu-Ni ^{[1
]}

He, Chiu-Hui ^{[1
]}

Yao, Ching-Fa ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 11-12期

关键词：

C-N bond formation; copper catalysts; dibenzodiazepinones; tandem processes; Ullmann coupling; SMILES REARRANGEMENT; QUINAZOLINONES; DERIVATIVES; OLANZAPINE; AMIDATION; LACTAMS; ALKYNES; AZIDE;

D O I：

10.1002/adsc.201301020

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1,4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro-8,15,22-triazapentacyclo[13.7.0.0(2,7).0(9,14).0(16,21)]docosa-1(22),2,4,6,9(14),10,12,16(21),17,19-decaene}.

引用

页码：2599 / 2608

页数：10

共 50 条

[31] Tetrahedron report 1134 Iron catalyzed C-N bond formation [J].

Ghorai, Sujit K. ;

Gopalsamuthiram, Vijaya G. ;

Jawalekar, Anup M. ;

Patre, Rupesh E. ;

Pal, Sitaram .

TETRAHEDRON, 2017, 73 (14) :1769-1794

[32] A Practical Synthesis of Indoles via a Pd-Catalyzed C-N Ring Formation [J].

Vaswani, Rishi G. ;

Albrecht, Brian K. ;

Audia, James E. ;

Cote, Alexandre ;

Dakin, Les A. ;

Duplessis, Martin ;

Gehling, Victor S. ;

Harmange, Jean-Christophe ;

Hewitt, Michael C. ;

Leblanc, Yves ;

Nasveschuk, Christopher G. ;

Taylor, Alexander M. .

ORGANIC LETTERS, 2014, 16 (16) :4114-4117

[33] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover [J].

Guimond, Nicolas ;

Gouliaras, Christina ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6908-+

[34] Copper-Catalyzed Oxidative C-H Bond Functionalization of N-Allylbenzamide for Regioselective C-N and C-O Bond Formation [J].

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[35] Copper-Catalyzed C-N Bond Formation via C-H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2-a]pyridines from N-(2-Pyridinyl)enaminones [J].

Cacchi, Sandro ;

Ciogli, Alessia ;

Demitri, Nicola ;

Fabrizi, Giancarlo ;

Ghirga, Francesca ;

Goggiamani, Antonella ;

Iazzetti, Antonia ;

Lamba, Doriano .

SYNTHESIS-STUTTGART, 2018, 50 (17) :3513-3519

[36] Metal-Free Intermolecular Oxidative C-N Bond Formation via Tandem C-H and N-H Bond Functionalization [J].

Kantak, Abhishek A. ;

Potavathri, Shathaverdhan ;

Barham, Rose A. ;

Romano, Kaitlyn M. ;

DeBoef, Brenton .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19960-19965

[37] Iron Mediated Desulfurization and C-N Bond Formation: Strategy for the Synthesis of Thioureas [J].

Pendem, Venkata Bhavanarushi ;

Nannapaneni, Madhavi .

LETTERS IN ORGANIC CHEMISTRY, 2018, 15 (12) :1025-1029

[38] Rh-Catalyzed tandem C-C/C-N bond formation of quinoxalines with alkynes leading to heterocyclic ammonium salts [J].

Talukdar, Kangkan ;

Roy, Subhasish ;

Bag, Raghunath ;

Punniyamurthy, Tharmalingam .

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[39] Tuning the Copper(II)/Copper(I) Redox Potential for More Robust Copper-Catalyzed C-N Bond Forming Reactions [J].

Cope, James D. ;

Valle, Henry U. ;

Hall, Ruby S. ;

Riley, Kathleen M. ;

Goel, Ekta ;

Biswas, Saborni ;

Hendrich, Michael P. ;

Wipf, David O. ;

Stokes, Sean L. ;

Emerson, Joseph P. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (14) :1278-1285

[40] Gold-catalyzed cascade C-C and C-N bond formation: synthesis of polysubstituted indolequinones and pyrroles [J].

Abdukader, Ablimit ;

Xue, Qicai ;

Lin, Aijun ;

Zhang, Ming ;

Cheng, Yixiang ;

Zhu, Chengjian .

TETRAHEDRON LETTERS, 2013, 54 (44) :5898-5900

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