Microwave-assisted synthesis of 5,6-dihydroindolo[1,2-a] quinoxaline derivatives through copper-catalyzed intramolecular N-arylation

被引：7

作者：

Zhao, Fei ^{[1
]}

Zhang, Lei ^{[1
]}

Liu, Hailong ^{[1
]}

Zhou, Shengbin ^{[1
]}

Liu, Hong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

基金：

中国国家自然科学基金;

关键词：

copper; 5,6-dihydroindolo[1,2-a]quinoxaline; intramolecular N-arylation; microwave irradiation; INDOLE ALKALOIDS; HETEROCYCLES; CHEMISTRY; EFFICIENT; CASCADE; AMINES; MILD; CUI;

D O I：

10.3762/bjoc.9.285

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical protocol has been developed to synthesize 5,6-dihydroindolo[ 1,2-a] quinoxaline derivatives by CuI-catalyzed intramolecular N-arylation under microwave irradiation. This method rapidly afforded the tetracyclic products with good to excellent yields (83-97%) in short reaction times (45-60 min).

引用

页码：2463 / 2469

页数：7

共 50 条

[21] Copper-catalyzed intramolecular oxidative amination of enaminone C-H bond for the synthesis of imidazo[1,2-a]pyridines
Wan, Jie-Ping
Hu, Deqing
Liu, Ying
Li, Luyao
Wen, Chengping
TETRAHEDRON LETTERS, 2016, 57 (26) : 2880 - 2883
[22] Microwave-Assisted Copper-Catalyzed Four-Component Tandem Synthesis of 3-N-Sulfonylamidine Coumarins
Murugavel, Govindarasu
Punniyamurthy, Tharmalingam
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12) : 6291 - 6299
[23] Regioselective Access to 1,2-Diarylhistidines through the Copper-Catalyzed N1-Arylation of 2-Arylhistidines
Sharma, Krishna K.
Mandloi, Meenakshi
Jain, Rahul
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (05) : 984 - 988
[24] A copper-catalyzed synthesis of benzo[4,5]imidazo[1,2-a]pyridine derivatives via C-N bond formation of 2-aminopyridines with arylboronic acids
Li, Xiao-Tang
Han, Chuan-Jie
Zhang, Zhan-Hui
RESEARCH ON CHEMICAL INTERMEDIATES, 2025, 51 (04) : 1733 - 1747
[25] One-Pot Synthesis of Triazolothiadiazepine 1,1-Dioxide Derivatives via Copper-Catalyzed Tandem [3+2] Cycloaddition/N-Arylation
Barange, Deepak Kumar
Tu, Yu-Chen
Kavala, Veerababurao
Kuo, Chun-Wei
Yao, Ching-Fa
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (01) : 41 - 48
[26] Synthesis of symmetrically and unsymmetrically substituted N,N′-diarylimidazolin-2-ones by copper-catalyzed arylamidation under microwave-assisted and conventional conditions
Hafner, Thomas
Kunz, Doris
SYNTHESIS-STUTTGART, 2007, (09): : 1403 - 1411
[27] Tandem Copper-Catalyzed Regioselective N-Arylation-Aza-Michael Addition: Synthesis of Tetracyclic 5H-Benzothiazolo[3,2-a]quinazoline Derivatives
Honnanayakanavar, Jyoti M.
Harish, Battu
Nanubolu, Jagadeesh Babu
Suresh, Surisetti
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) : 8780 - 8791
[28] Microwave-Assisted, Metal-Free, Base-Mediated C-N Bond Formation/Cleavage: Synthesis of Benzimidazo[1,2-a]quinazoline Derivatives
Kumar, Prashant
Singh, Anil K.
Bahadur, Vijay
Len, Christophe
Richards, Nigel G. J.
Parmar, Virinder S.
Van der Eycken, Erik V.
Singh, Brajendra K.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2016, 4 (04): : 2206 - 2210
[29] Design and synthesis of 1,2-dihydroquinoline/chromene fused sugar triazole frameworks by copper-catalyzed one-pot click and intramolecular arylation reactions
Ahemad, Mohammed Ansar
Nayak, Sabita
Prusty, Kamalika
Panigrahi, Gopinatha
Mohapatra, Suhasini
Mohapatra, Seetaram
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (33) : 6748 - 6762
[30] Copper-Catalyzed N-Arylation/Hydroamin(d)ation Domino Synthesis of Indoles and its Application to the Preparation of a Chek1/KDR Kinase Inhibitor Pharmacophore
Ackermann, Lutz
Barfuesser, Sebastian
Potukuchi, Harish K.
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) : 1064 - 1072

← 1 2 3 4 5 →