An efficient and convenient synthesis of heterocycle-fused indazoles via the N-N bond forming reaction of nitroarenes induced by low-valent titanium reagent

被引：15

作者：

Lin, Wei ^{[1
]}

Hu, Ming-Hua ^{[1
]}

Feng, Xian ^{[1
]}

Cao, Cheng-Pao ^{[1
]}

Huang, Zhi-Bin ^{[1
]}

Shi, Da-Qing ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 32期

关键词：

Indolo[2 ',3 ':3,4]pyrido[1,2-b]indazole; 5,6-Dihydroindazolo[3,2-a]isoquinoline; Nitro-aryl; Reductive cyclization; Low-valent titanium reagent; ONE-POT SYNTHESIS; SNCL2-MEDIATED CYCLIZATION; COUPLING REACTIONS; DERIVATIVES; 2-NITROBENZYLAMINES; 2H-INDAZOLES; INHIBITORS; MOLECULES; DESIGN; AID;

D O I：

10.1016/j.tet.2013.05.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient one-pot protocol for the preparation of 8,13-dihydro-7H-indolo[2',3':3,4]pyrido[1,2-b]indazole and 5,6-dihydroindazolo[3,2-a]isoquinoline via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent has been developed. The attractive features of the current method include an N-N bond formation and the selective reduction of the C=N bond and nitro group, both of which were easily achieved in one-pot by controlling the pH of the reaction mixture. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6721 / 6726

页数：6

共 42 条

[1] PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].