Three-component, four-centered, one-pot synthesis of 1-(arylethynyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole derivatives

被引：2

作者：

Reddy, B. V. Subba ^{[1
]}

Kota, Kavya ^{[1
,2
]}

Babu, R. Anji ^{[1
]}

Khan, P. Rasvan ^{[1
]}

Mukkanti, K. ^{[2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Ctr Semiochem, Hyderabad 500007, Andhra Pradesh, India

[2] JNTU, Dept Chem, Hyderabad 500085, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 22期

关键词：

Three component reaction; Halocyclization; Cyclic iminium ion; Alkyne addition; Tetrahydrocarbolines; TETRAHYDRO-BETA-CARBOLINES; PICTET-SPENGLER REACTION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; MULTICOMPONENT REACTIONS; ALKALOIDS; TETRAHYDROISOQUINOLINES; CYCLIZATION; STRATEGIES; CHEMISTRY;

D O I：

10.1016/j.tetlet.2017.04.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient three component, four-centered A3 coupling strategy has been developed for the synthesis of a novel series of 1-arylethynyl-tetrahydro-beta-carboline derivatives in good yields with high selectivity. This method is also useful for the preparation of 1-arylethynyl tetrahydroisoquinolines, which can be used for the synthesis of biologically active molecules such as homolaudanosine, dysoxyline, methopo-line and almorexant. The use of a readily available ZnCl2/Et3N reagent system makes this method simple, convenient and practical. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2088 / 2093

页数：6

共 50 条

[41] Three-component one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives in hexafluoroisopropanol
Zhou, Jie
Xu, Bai Ling
CHINESE CHEMICAL LETTERS, 2008, 19 (08) : 921 - 924
[42] Three-component one-pot synthesis of 1,2,3,4-tetrahydroquinoline derivatives in hexafluoroisopropanol
Jie Zhou Bai Ling Xu~* Institute of Materia Medica
Chinese Chemical Letters, 2008, (08) : 921 - 924
[43] Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine
Baiget, Jessica
Llona-Minguez, Sabin
Lang, Stuart
MacKay, Simon P.
Suckling, Colin J.
Sutcliffe, Oliver B.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1407 - 1411
[44] Simple synthesis of 6-(trifluoromethyl)-2,4,5,6-tetrahydropyrazolo[3,4-b]pyran derivatives by one-pot, three-component reactions
Li, Dong-Mei
Song, Li-Ping
Li, Xian-Fu
Xing, Chun-Hui
Peng, Wei-Min
Zhu, Shi-Zheng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) : 3520 - 3525
[45] Efficient synthesis of functionalized spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via one-pot three-component reaction
Wang, Chao
Jiang, Yan-Hong
Yan, Chao-Guo
MOLECULAR DIVERSITY, 2014, 18 (04) : 809 - 820
[46] Novel one-pot synthesis of pyrazolo[3,4-b][1,4]oxazines
Raslan, MA
Abd El Latif, FM
Otto, HH
Sadek, KU
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2000, 47 (4B) : 947 - 949
[47] One-Pot Combinatorial Synthesis of 4-Aryl-1H-thiopyrano[3,4-b]pyridine-5-one Derivatives
Yao, Chang-Sheng
Wang, Cui-Hua
Jiang, Bei
Tu, Shu-Jiang
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04): : 472 - 475
[48] One-pot Three-component Synthesis of Spiro[pyrazolo[3,4-b]pyridine-4,3′-indoline] Derivatives Catalyzed by Melamine Trisulfonic Acid
Yang, Li-Min
Sun, Peng-Li
Wu, Li-Qiang
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2012, 59 (12) : 1500 - 1503
[49] The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy) acetate, C19H18N2O3
Wang Li-Hua
Tai Xi-Shi
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2020, 235 (06): : 1275 - 1276
[50] Three-component, one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by bromodimethylsulfonium bromide
A. Shaabani
A. Maleki
Chemical Papers, 2007, 61 : 333 - 336

← 1 2 3 4 5 →