KOtBu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones

被引：149

作者：

Bhakuni, Bhagat Singh ^{[1
]}

Kumar, Amit ^{[1
]}

Balkrishna, Shah Jaimin ^{[1
]}

Sheikh, Javeed Ahmed ^{[1
]}

Konar, Sanjit ^{[1
]}

Kumar, Sangit ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, IISER, Bhopal 462023, MP, India

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

关键词：

C-H ACTIVATION; INTRAMOLECULAR ARYLATION; METHODOLOGY; BUTOXIDE; ARYL; DERIVATIVES; ALKALOIDS; EBSELEN; ANALOGS; BIARYLS;

D O I：

10.1021/ol301077y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon-carbon bond forming reaction gives direct access to various blaryl lactams containing six- and seven-membered rings chemoselectively. Carbon-carbon coupling seems to proceed by the generation of a radical In the amide ring which leads to C-H arylation of aniline.

引用

页码：2838 / 2841

页数：4

共 45 条

[1] SYNTHESIS OF ZANTHOXYLINE AND ITS RELATED COMPOUNDS: REVISION OF THE REPORTED STRUCTURE [J].

Abe, Hitoshi ;

Kobayashi, Naoko ;

Takeuchi, Yasuo ;

Harayama, Takashi .

HETEROCYCLES, 2010, 80 (02) :873-877

[2] Diels-Alder approach to biaryls: Elucidation of competing tandem [2+2] cycloaddition/[1,3] sigmatropic shift pathway [J].

Ashburn, Bradley O. ;

Carter, Rich G. ;

Zakharov, Lev N. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) :7305-7309

[3] Direct Transition-Metal-Free Intramolecular Arylation of Phenols [J].

Bajracharya, Gan B. ;

Daugulis, Olafs .

ORGANIC LETTERS, 2008, 10 (20) :4625-4628

[4] A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water [J].

Balkrishna, Shah Jaimin ;

Kumar, Sangit .

SYNTHESIS-STUTTGART, 2012, 44 (09) :1417-1426

[5] Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Kumar, Sangit .

TETRAHEDRON, 2011, 67 (49) :9565-9575

[6] Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se-N Heterocycles [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Chopra, Deepak ;

Kumar, Sangit .

ORGANIC LETTERS, 2010, 12 (23) :5394-5397

[7] Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters [J].

Banwell, MG ;

Lupton, DW ;

Ma, XH ;

Renner, J ;

Sydnes, MO .

ORGANIC LETTERS, 2004, 6 (16) :2741-2744

[8] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams [J].

Baudoin, O ;

Cesario, M ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) :1199-1207

[9] A simple general approach to phenanthridinones via palladium-catalyzed intramolecular direct arene arylation [J].

Bernini, Roberta ;

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio .

SYNTHESIS-STUTTGART, 2008, (05) :729-738

[10] An efficient copper mediated synthetic methodology for benzo[d]isothiazol-3(2H)-ones and related sulfur-nitrogen heterocycles [J].

Bhakuni, Bhagat Singh ;

Balkrishna, Shah Jaimin ;

Kumar, Amit ;

Kumar, Sangit .

TETRAHEDRON LETTERS, 2012, 53 (11) :1354-1357

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