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

[21] InBr3-catalyzed three-component, one-pot synthesis of imidazo[1,2-a]pyridines [J].

Reddy, B. V. Subba ;

Reddy, P. Sivaramakrishna ;

Reddy, Y. Jayasudhan ;

Yadav, J. S. .

TETRAHEDRON LETTERS, 2011, 52 (44) :5789-5793

[22] Three-component one-pot synthesis of novel pyrido[2,3-d]pyrimidine indole substituted derivatives and DFT analysis [J].

Rangel, Jovanni ;

Diaz-Uribe, Carlos ;

Rodriguez-Serrano, Angela ;

Zarate, Ximena ;

Serge, York ;

Vallejo, William ;

Nogueras, Manuel ;

Trilleras, Jorge ;

Quiroga, Jairo ;

Tatchen, Jorg ;

Cobo, Justo .

JOURNAL OF MOLECULAR STRUCTURE, 2017, 1137 :431-439

[23] A Clean and Expedient Synthesis of Pyrido[1,4]oxazepino Spiropyrrolidines Through One-Pot, Three-Component [3+2] Cycloaddition Reaction [J].

Kathiravan, S. ;

Babu, A. R. Suresh ;

Raghunathan, R. .

SYNTHETIC COMMUNICATIONS, 2010, 40 (24) :3721-3727

[24] One-pot, three-component synthesis of novel coumarinyl-pyrazolo[3,4-b]pyridine-3-carboxylate derivatives using [AcMIm]FeCl4 as recyclable catalyst [J].

Ambati, Srinivasa Rao ;

Patel, Jeevan Lal ;

Chandrakar, Komal ;

Sarkar, Uttam ;

Penta, Santhosh ;

Banerjee, Subhash ;

Varma, Rajender S. .

JOURNAL OF MOLECULAR STRUCTURE, 2022, 1268

[25] A novel, one-pot, three-component synthesis of 5H-[1,3]Thiazolo[3,2-a]pyrimidine derivatives [J].

Adib, Mehdi ;

Nosrati, Meisam ;

Mahdavi, Mohammad ;

Zhu, Long-Guan ;

Mirzaei, Peiman .

SYNLETT, 2007, (17) :2703-2706

[26] Bionanostructure-catalyzed one-pot three-component synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent-free conditions [J].

Maleki, Ali ;

Paydar, Reza .

REACTIVE & FUNCTIONAL POLYMERS, 2016, 109 :120-124

[27] Rapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives via one-pot three component reaction using organocatalysis [J].

Singh, Shivendra ;

Srivastava, Anvita ;

Samanta, Sampak .

TETRAHEDRON LETTERS, 2012, 53 (45) :6087-6090

[28] One-Pot Three-Component Synthesis of 3-(1H-Benzo[d]imidazol-2-yl)chromen Derivatives [J].

Wang, Xiang ;

Chen, Ping ;

Zhi, Sanjun ;

Hu, Huayou ;

Kan, Yuhe ;

Zhang, Zaichao .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) :3299-3303

[29] Catalyzed synthesis of functionalized pyrrolo[3,4-b]quinolines via one-pot three-component reactions under conventional and nonconventional conditions [J].

Renata I. Eften’eva ;

Oleg V. Kushnir ;

Oleksandr S. Lyavinets ;

Ionel I. Mangalagiu ;

Myhailo V. Vovk .

Monatshefte für Chemie - Chemical Monthly, 2017, 148 :1745-1752

[30] One-pot three-component synthesis of pyrido [2′,1′: 2,3] imidazo[4,5-c] isoquinolines using Fe3O4@SiO2-OSO3H as an efficient heterogeneous nanocatalyst [J].

Maleki, Ali .

RSC ADVANCES, 2014, 4 (109) :64169-64173

← 1 2 3 4 5 →