A Convenient Electrochemical One-Pot Direct Synthesis of 2H-Indazoles via N-N Coupling

被引:0
作者
Upadhyay, Abhishek [1 ]
Moulekhi, Sumit [1 ]
Singh, Vinay Kumar [2 ]
Singh, Manjula [3 ]
Patel, Manoj Kumar [4 ]
Mishra, G. K. [1 ]
Gupta, L. P. [1 ]
Awasthi, N. K. [1 ]
Singh, R. K. P. [4 ]
机构
[1] Univ Lucknow, BSNV Post Grad Coll, Dept Chem, Lucknow, India
[2] DN PG Coll, Dept Chem, Bulandshahr, India
[3] Govt Engn Coll, Dept Chem, Jamui, India
[4] Univ Allahabad, Dept Chem, Electrochem Lab Green Synth, Allahabad, India
关键词
2H-Indazoles; electrosynthesis; hydrazine-and metal-free; mild reaction condition; N-N coupling; one pot synthesis; 3 COMPONENT SYNTHESIS; HETEROCYCLIC-COMPOUNDS; BOND FORMATION; INDAZOLES; ELECTROSYNTHESIS; INHIBITORS; AZIDES; MILD;
D O I
10.1002/jhet.70018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article describes an environmentally friendly synthesis of a 2H-indazole derivative via N-N bond coupling using the interaction of 2-azidobenzaldehyde and aniline in EtOH solvent. Constant Current electrosynthesis was performed in an undivided cell at ambient temperature with tetrabutylammonium hexafluorophosphate (Bu4NPF6) as a supporting electrolyte. The protocol's enticing qualities include clean synthesis, the use of electricity rather than chemical reagents, and atom economy.
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页数:6
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共 42 条
[1]   Highly Efficient One-Pot Three Component Synthesis of 2H-Indazoles by Consecutive Condensation, C-N and N-N Bond Formations Using Cu/Aminoclay/Reduced Graphene Oxide Nanohybrid [J].
Behrouz, Somayeh .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (03) :1863-1871
[2]   Recent Synthetic Approaches to 1H-and 2H-Indazoles. A Review [J].
Cankarova, Nadezda ;
Hlavac, Jan ;
Krchnak, Viktor .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2010, 42 (05) :433-465
[3]   Unparalleled Ease of Access to a Library of Biheteroaryl Fluorophores via Oxidative Cross-Coupling Reactions: Discovery of Photostable NIR Probe for Mitochondria [J].
Cheng, Yangyang ;
Li, Gaocan ;
Liu, Yang ;
Shi, Yang ;
Gao, Ge ;
Wu, Di ;
Lan, Jingbo ;
You, Jingsong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4730-4738
[4]   Electro-Organic Synthesis of New Pyrimidine and Uracil Derivatives [J].
Davarani, Saied Saeed Hosseiny ;
Fumani, Neda Sheijooni ;
Vahidi, Siavash ;
Tabatabaei, Mohammad-Ali ;
Arvin-Nezhad, Hamid .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (01) :40-45
[5]   A convenient electro-catalyzed multicomponent synthesis of 4H-thiopyran derivatives [J].
Dubey, Rahul ;
Singh, Vinay K. ;
Sharma, Laxmi Kant ;
Upadhyay, Abhishek ;
Kumar, Narendra ;
Singh, Rana Krishna Pal .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (16) :7836-7839
[6]   Functionalization of indazoles by means of transition metal-catalyzed cross-coupling reactions [J].
El Kazzouli, Said ;
Guillaumet, Gerald .
TETRAHEDRON, 2016, 72 (43) :6711-6727
[7]   Structure-activity relationships, and drug metabolism and pharmacokinetic properties for indazole piperazine and indazole piperidine inhibitors of ROCK-II [J].
Feng, Yangbo ;
Cameron, Michael D. ;
Frackowiak, Bozena ;
Griffin, Evelyn ;
Lin, Li ;
Ruiz, Claudia ;
Schroter, Thomas ;
LoGrasso, Philip .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2355-2360
[8]   Synthesis of indazole motifs and their medicinal importance: An overview [J].
Gaikwad, Digambar D. ;
Chapolikar, Archana D. ;
Devkate, Chandrashekhar G. ;
Warad, Khandu D. ;
Tayade, Amit P. ;
Pawar, Rajendra P. ;
Domb, Abraham J. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :707-731
[9]   Design and synthesis of pyridone inhibitors of non-nucleoside reverse transcriptase [J].
Gomez, Robert ;
Jolly, Samson ;
Williams, Theresa ;
Tucker, Thomas ;
Tynebor, Robert ;
Vacca, Joe ;
McGaughey, Georgia ;
Lai, Ming-Tain ;
Felock, Peter ;
Munshi, Vandna ;
DeStefano, Daniel ;
Touch, Sinoeun ;
Miller, Mike ;
Yan, Youwei ;
Sanchez, Rosa ;
Liang, Yuexia ;
Paton, Brenda ;
Wan, Bang-Lin ;
Anthony, Neville .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7344-7350
[10]  
Grimshaw J., 2000, Electrochemical Reactions and Mechanisms in Organic Chemistry