Palladium/Norbornene Chemistry in the Synthesis of Polycyclic Indolines with Simple Nitrogen Sources

被引：8

作者：

Ghasemi, Mehran ^{[1
,2
]}

Jafarpour, Farnaz ^{[1
]}

Habibi, Azizollah ^{[2
]}

机构：

[1] Univ Tehran, Coll Sci, Sch Chem, Tehran 141556455, Iran

[2] Kharazmi Univ, Fac Chem, 43 Mofateh St,Fnghelab Ave, Tehran 1571914911, Iran

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 14期

关键词：

amines; N-alkylindolines; norbornene; palladacycle; urea; CATALYZED INTRAMOLECULAR AMINATION; AROMATIC FUNCTIONALIZATION; PALLADIUM; C(SP(2))-H; CYCLIZATION; DERIVATIVES; NORBORNENE; ALKALOIDS; ROUTE; BONDS;

D O I：

10.1055/s-0039-1707988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient procedure has been developed to synthesize -indoline derivatives through a palladium-catalyzed Heck reaction/C-H activation/dual amination cascade in one pot. This constitutes the first intermolecular catalytic approach to directly accessN-alkylindolines with a broad substrate scope in the absence of any ligands. This method highlights the use of readily available amines and ureas as the required nitrogen sources in building up the indoline core.

引用

页码：2092 / 2098

页数：7

共 59 条

[41] DOSE-RESPONSE DATA FOR TOXIFERINE DICHLORIDE IN MONKEYS AND GUINEA-PIGS [J].

ROSATO, RR ;

STEPHEN, EL ;

PANNIER, WL .

TOXICOLOGY AND APPLIED PHARMACOLOGY, 1976, 35 (01) :107-111

[42] Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3-b]indole [J].

Ruiz-Sanchis, Pau ;

Savina, Svetlana A. ;

Albericio, Fernando ;

Alvarez, Mercedes .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (05) :1388-1408

[43] A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C-N Cyclization/Aromatization [J].

Sayyad, Masthanvali ;

Nanaji, Yerramsetti ;

Ghorai, Manas K. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12659-12667

[44] Recent advances in indoline synthesis [J].

Silva, Thiago S. ;

Rodrigues, Manoel T., Jr. ;

Santos, Hugo ;

Zeoly, Lucas A. ;

Almeida, Wanda P. ;

Barcelos, Rosimeire C. ;

Gomes, Ralph C. ;

Fernandes, Fabio S. ;

Coelho, Fernando .

TETRAHEDRON, 2019, 75 (14) :2063-2097

[45] Synthesis of Indolines by Copper-Mediated Intramolecular Aromatic C-H Amination [J].

Takamatsu, Kazutaka ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3242-3249

[46]

Triggle David J., 1998, CNS Drug Reviews, V4, P87, DOI 10.1111/j.1527-3458.1998.tb00059.x

[47] Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions [J].

Wang, Chao ;

Chen, Changpeng ;

Zhang, Jingyu ;

Han, Jian ;

Wang, Qian ;

Guo, Kun ;

Liu, Pei ;

Guan, Mingyu ;

Yao, Yingming ;

Zhao, Yingsheng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9884-9888

[48] Palladium/Norbornene Cooperative Catalysis [J].

Wang, Jianchun ;

Dong, Guangbin .

CHEMICAL REVIEWS, 2019, 119 (12) :7478-7528

[49] Palladium-Catalyzed Synthesis of Indolines from Aroyloxycarbamates through a Tandem Decarboxylative Amination/Heck/Annulation Reaction [J].

Wang, Zheng ;

Li, Peihe ;

Fu, Hui ;

Dai, Qipu ;

Hu, Changwen .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) :192-200

[50] Alkaloids from Portulaca oleracea L. [J].

Xiang, L ;

Xing, DM ;

Wang, W ;

Wang, RF ;

Ding, Y ;

Du, LJ .

PHYTOCHEMISTRY, 2005, 66 (21) :2595-2601

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