Iron(II)-catalyzed direct C-H cyanoalkylation of 2H-indazoles and coumarins via radical C-C bond cleavage

被引:20
作者
Gao, Pin [1 ]
Cheng, Yuan-Bo [1 ]
Yang, Fan [1 ]
Guo, Li-Na [1 ]
Duan, Xin-Hua [1 ]
机构
[1] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian Key Lab Sustainable Energy Mat Chem, Dept Chem,Sch Sci, Xian 710049, Shaanxi, Peoples R China
基金
中国博士后科学基金;
关键词
Iron; Cyanoalkylation; Heterocycles; Radical; REGIOSELECTIVE SYNTHESIS; RING-CLEAVAGE; OXIME ESTERS; FUNCTIONALIZATION; INHIBITORS; FLAVONES; ACCESS; ETHERS; ACIDS;
D O I
10.1016/j.tetlet.2019.150967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An iron-catalyzed C-3 cyanoalkylation of 2H-indazole and coumarin derivates with cyclobutanone oxime esters has been accomplished, which proceeds efficiently in a high regioselective manner to construct diverse alkylated 2H-indazole and coumarin derivates in moderate to good yields. Preliminary mechanistic studies reveal that a distal cyanosubstituted alkyl radicals intermediate would be formed through radical-involved C-C bond cleavage of cyclobutanone oximes ester. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
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共 47 条
[1]   Syntheses of lipophilic chalcones and their conformationally restricted analogues as antitubercular agents [J].
Ahmad, Imran ;
Thakur, Jay Prakash ;
Chanda, Debabrata ;
Saikia, Dharmendra ;
Khan, Feroz ;
Dixit, Shivani ;
Kumar, Amit ;
Konwar, Rituraj ;
Negi, Arvind Singh ;
Gupta, Atul .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) :1322-1325
[2]   Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles [J].
Ai, Wenying ;
Liu, Yaqian ;
Wang, Qian ;
Lu, Zhonglin ;
Liu, Qiang .
ORGANIC LETTERS, 2018, 20 (02) :409-412
[3]   A review on coumarins as acetylcholinesterase inhibitors for Alzheimer's disease [J].
Anand, Preet ;
Singh, Baldev ;
Singh, Nirmal .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (03) :1175-1180
[4]   Direct Acyl Radical Addition to 2H-Indazoles Using Ag-Catalyzed Decarboxylative Cross-Coupling of α-Keto Acids [J].
Bogonda, Ganganna ;
Kim, Hun Young ;
Oh, Kyungsoo .
ORGANIC LETTERS, 2018, 20 (09) :2711-2715
[5]   RING-OPENING INDUCED BY IMINYL RADICALS DERIVED FROM CYCLOBUTANONES - NEW ASPECTS OF TIN HYDRIDE CLEAVAGE OF S-PHENYL SULFENYLIMINES [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1055-1057
[6]   A NEW AND SYNTHETICALLY USEFUL SOURCE OF IMINYL RADICALS [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
TETRAHEDRON LETTERS, 1991, 32 (34) :4299-4302
[7]   Manganese(III)-mediated direct Csp2-H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate [J].
Cao, Xiao-Hui ;
Pan, Xiangqiang ;
Zhou, Peng-Jun ;
Zou, Jian-Ping ;
Asekun, Olayinka Taiwo .
CHEMICAL COMMUNICATIONS, 2014, 50 (25) :3359-3362
[8]   Synthesis, Molecular Modeling, and Selective Inhibitory Activity against Human Monoamine Oxidases of 3-Carboxamido-7-Substituted Coumarins [J].
Chimenti, Franco ;
Secci, Daniela ;
Bolasco, Adriana ;
Chimenti, Paola ;
Bizzarri, Bruna ;
Granese, Arianna ;
Carradori, Simone ;
Yanez, Matilde ;
Orallo, Francisco ;
Ortuso, Francesco ;
Alcaro, Stefano .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (07) :1935-1942
[9]   Paclitaxel, cisplatin and lonidamine in advanced ovarian cancer. A phase II study [J].
De Lena, M ;
Lorusso, V ;
Latorre, A ;
Fanizza, G ;
Gargano, G ;
Caporusso, L ;
Guida, M ;
Catino, A ;
Crucitta, E ;
Sambiasi, D ;
Mazzei, A .
EUROPEAN JOURNAL OF CANCER, 2001, 37 (03) :364-368
[10]   Direct C-H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C-C Bonds Formation [J].
Gao, Pin ;
Gu, Yu-Rui ;
Duan, Xin-Hua .
SYNTHESIS-STUTTGART, 2017, 49 (15) :3407-3421