Ir(III)-Catalyzed [4+2] cyclization of azobenzene and diazotized Meldrum's acid for the synthesis of cinnolin-3(2H)-one

被引：16

作者：

Borah, Gongutri ^{[1
,2
]}

Patel, Pitambar ^{[1
,2
]}

机构：

[1] CSIR North East Inst Sci & Technol, Chem Sci & Technol Div, Jorhat 785006, Assam, India

[2] CSIR North East Inst Sci & Technol, Acad Sci & Innovat Res AcSIR, Jorhat 785006, Assam, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 09期

关键词：

C-H FUNCTIONALIZATION; RHODIUM(III)-CATALYZED SYNTHESIS; CARBENOID FUNCTIONALIZATION; BOND FUNCTIONALIZATION; CINNOLINIUM SALTS; ANNULATION; ACCESS; IRIDIUM; RHODIUM; ISOQUINOLINES;

D O I：

10.1039/c8ob03214a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first report on Ir(III)-catalyzed C-H alkylation/cyclization of azobenzene with diazotized Meldrum's acid is described for the synthesis of cinnolin-3(2H)-one derivatives under mild conditions. Controlled experiments led to the isolation of intermediate ortho-alkylated product of azobenzene, which was converted to both cinnolin-3(2H)-one-4-carboxylic acid and its ester derivative. Additionally, the iridacyclic complex of azobenzene was isolated and found to be an active intermediate in the catalytic cycle.

引用

页码：2554 / 2563

页数：10

共 50 条

[31] Selective Synthesis of Indazolo[2,3-a]quinolines via Rh(III)-Catalyzed Oxidant-Free [4+2] or [5+1] Annulation of 2-Aryl-2H-indazoles with α-Diazo Carbonyl Compounds [J].

Guo, Shenghai ;

Sun, Lincong ;

Li, Xuzhuo ;

Zhang, Xinying ;

Fan, Xuesen .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (04) :913-926

[32] Rhodium(III)-Catalyzed [4+2] Annulation of N-Hydroxyoximes with Maleate Esters/2-Chloroacrylates: Synthesis of Isoquinoline-3,4-Dicarboxylates and Isoquinoline-3-Carboxylates [J].

Li, He ;

Chen, Tao ;

Wang, Zhiwei ;

Li, Yuxin ;

Wu, Baoheng ;

Xu, Ning ;

Lu, Ye ;

Jin, Xinxin ;

Yu, Jiaqi ;

Liu, Jinglin ;

Bao, Ming .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (08)

[33] Ru(II)-catalyzed cyclization of 1-aryl-5-aminopyrazoles and α-diazolidinones for one-pot synthesis of benzopyrazole[1,3]diazepines in H2O/EtOH [J].

Liu, Fu-Rao ;

Ren, Jun-Jie ;

Wang, Meng-Yao ;

Liu, Hao-Yu ;

Cao, Jian-Kang ;

Ding, Yu ;

Xue, Zi-Han ;

Zhang, Xin-Shuang ;

Zhu, Yan-Ping ;

Sun, Yuan-Yuan .

TETRAHEDRON, 2024, 160

[34] Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones [J].

Lu, Shengle ;

Tu, Xianxia ;

Liu, Weishun ;

Shen, Liting ;

Mao, Shanjian ;

Deng, Guisheng .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (07) :1663-1672

[35] Synthesis of [1,2,3]Triazolo-[1,5-a]quinoxalin-4(5H)-ones through Photoredox-Catalyzed [3+2] Cyclization Reactions with Hypervalent lodine(III) Reagents [J].

Wen, Jinxia ;

Zhao, Wenyan ;

Gao, Xu ;

Ren, Xiaofang ;

Dong, Chunping ;

Wang, Cheli ;

Liu, Li ;

Li, Jian .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06) :4415-4423

[36] Rhodium(III)-catalyzed benzo[c]azepine-1,3(2H)-dione synthesis via tandem C-H alkylation and intermolecular amination of N-methoxylbenzamide with 3-bromo-3,3-difluoropropene [J].

Xu, Xu ;

Zhou, Guanyu ;

Ju, Guodong ;

Wang, Dongjie ;

Li, Bao ;

Zhao, Yingsheng .

CHINESE CHEMICAL LETTERS, 2022, 33 (02) :847-850

[37] Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation [J].

Chen, Junyu ;

Zhong, Tianshuo ;

Zheng, Xiangyun ;

Yin, Chuanliu ;

Zhang, Lei ;

Zhou, Jian ;

Jiang, Xinpeng ;

Yu, Chuanming .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) :446-452

[38] Synthesis of new cyclazines and 4,5-diaryl-1H-pyrrol-3(2H)-one units in discoipyrroles from indolizinone-DMAD cycloadducts [J].

Kurian, Jais ;

Kannoth, Muraleedharan M. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (39) :8832-8848

[39] Rh(III)-Catalyzed Domino [4+2] Annulation/Aza-Michael Addition of N-(Pivaloyloxy)benzamides with 1,5-Enynes via C-H Activation: Synthesis of Functionalized Aromathecins [J].

Reddy, Chada Raji ;

Mallesh, Kathe ;

Bodasu, Srinivas ;

Donthiri, Ramachandra Reddy .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12) :7905-7915

[40] Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol [J].

Dang, Xinxin ;

He, Yu ;

Liu, Yingtian ;

Chen, Xuehong ;

Li, Jun-Long ;

Zhou, Xian-Li ;

Jiang, Hezhong ;

Li, Jiahong .

RSC ADVANCES, 2018, 8 (52) :30050-30054

← 1 2 3 4 5 →