Electrophilic Cyclization of Aryl Propargylic Alcohols: Synthesis of Dihalogenated 6,9-Dihydropyrido[1,2-a]indoles via a Cascade lodocyclization

被引：19

作者：

Wang, Jia ^{[1
]}

Zhu, Hai-Tao ^{[2
]}

Chen, Si ^{[1
]}

Xia, Yu ^{[1
]}

Jin, Dong-Po ^{[1
]}

Qui, Yi-Feng ^{[1
]}

Li, Ying-Xiu ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Baoji Univ Arts & Sci, Shannxi Key Lab Phytochem, Baoji 721013, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

基金：

美国国家科学基金会;

关键词：

REGIOSELECTIVE SYNTHESIS; N-HETEROCYCLES; SUBSTITUTED ISOQUINOLINES; TANDEM CYCLIZATION; FACILE SYNTHESIS; DERIVATIVES; INDOLES; ALKYNES; CYCLOADDITION; NUCLEOPHILES;

D O I：

10.1021/acs.joc.6b02013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for the synthesis of 6,9-dihydropyrido[1,2-a]indoles through a cascade iodocyclization of 4-(3-methyl-1H-indol-1-yl)-1,1-diphenylbut-2-yri-1-ol derivatives is presented. This reaction was conducted under very mild conditions and in a short time. The reactions are metal-free, are environmentally friendly and give up to 94% yield. Moreover, the obtained halides allow functional group diversification by palladium-catalyzed coupling reactions, which could act as potential intermediates for the synthesis of valuable compounds.

引用

页码：10975 / 10986

页数：12

共 33 条

[31] Synthesis of Imidazo[1,2-a]pyridine-Fused 1,3-Benzodiazepine Derivatives with Anticancer Activity via a One-Pot Cascade GBB-3CR/Pd(II)-Catalyzed Azide-Isocyanide Coupling/Cyclization Process
Zhong, Cheng-Ran
Zhang, Yang-Hong
Yao, Gang
Zhu, Hai-Li
Hu, Yin-Di
Zeng, Zhi-Gang
Liao, Chang-Zhou
He, Hui-Ting
Luo, Ya-Ting
Xiong, Jun
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (18): : 13125 - 13134
[32] Efficient two-step synthesis of 3-halo-3-enals or 2-halo-2-alkenyl ketones from propargylic bromides via a unique cationic 1,2-aryl or proton shift in electrophilic addition reaction of 2,3-allenols with X+
Fu, CL
Li, J
Ma, SM
CHEMICAL COMMUNICATIONS, 2005, (32) : 4119 - 4121
[33] Ultrasound-Assisted Expedient and Green Synthesis of a New Series of Diversely Functionalized 7-Aryl/heteroarylchromeno[4,3-d]pyrido[1,2-a]pyrimidin-6(7H)-ones via One-Pot Multicomponent Reaction under Sulfamic Acid Catalysis at Ambient Conditions
Brahmachari, Goutam
Karmakar, Indrajit
Nurjamal, Khondekar
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (08): : 11018 - 11028

← 1 2 3 4 →