Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl3/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4H-carbazol-4-ones and Related Heterocycles

被引：17

作者：

Qiu, Yun ^{[1
]}

Dlugosch, Michael ^{[2
]}

Liu, Xin ^{[2
]}

Khan, Faiyaz ^{[2
]}

Ward, Jas S. ^{[2
]}

Lan, Ping ^{[1
]}

Banwell, Martin G. ^{[2
]}

机构：

[1] Jinan Univ, Dept Food Sci & Engn, Guangzhou 510632, Guangdong, Peoples R China

[2] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 2601, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

澳大利亚研究理事会;

关键词：

PALLADIUM-CATALYZED SYNTHESIS; AROMATIC NITROCOMPOUNDS; TITANIUM(III) CHLORIDE; INDOLES; ALPHA; 1,2-DIHYDRO-4(3H)-CARBAZOLONES; RESOLUTION;

D O I：

10.1021/acs.joc.8b01940

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compounds such as 3, the product of a palladium[0]-catalyzed Ullmann cross-coupling of o-iodonitrobenzene and 2-iodocyclohex-2-en-1-one, undergo complementary modes of reductive cyclization depending upon the conditions employed. Thus, on treatment with hydrogen in the presence of palladium on carbon, the tetrahydrocarbazole 4 is formed, while reaction of the same substrate (3) with TiCl3 in acetone affords the 1,2,3,9-tetrahydro-4H-carbazol-4-one 6.

引用

页码：12023 / 12033

页数：11