An efficient one-pot synthesis of acenaphtho[1,2-b]indolindeneone and acenaphtho[1,2-b]indoldione derivatives

被引:1
作者
Amiri, Zeinab [1 ]
Bayat, Mohammad [1 ]
机构
[1] Imam Khomeini Int Univ, Fac Sci, Chem Dept, Qazvin, Iran
关键词
Acenaphthenequinone; 3-Indondione; One -pot reaction; Acenaphthoindole systems; Dimedone; Introduction; INDOLE; CYCLIZATION; ANNULATION;
D O I
10.1016/j.tetlet.2023.154578
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple method for the synthesis of acenaphtho[1,2-b]indolindenedione derivatives and acenaphtho [1,2-b]indolone derivatives via four-component reaction is described. The reaction between dimedone, arylamines, acenaphthoquinone, and 1,3-indondione in refluxing ethanol under catalyst-free conditions are produced the title compounds. The advantages of this method are: environmental friendly, short reac-tion time, easy work-up, and high yield.& COPY; 2023 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 33 条
[1]  
[Anonymous], 1996, Indoles
[2]   Synthesis of carbazolones and 3-acetylindoles via oxidative C-N bond formation through PIFA-mediated annulation of 2-aryl enaminones [J].
Ban, Xu ;
Pan, Yan ;
Lin, Yingfu ;
Wang, Songqing ;
Du, Yunfei ;
Zhao, Kang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) :3606-3609
[3]   Thiopyrano[2,3-e]indol-2-ones: Angelicin heteroanalogues with potent photoantiproliferative activity [J].
Barraja, Paola ;
Diana, Patrizia ;
Montalbano, Alessandra ;
Carbone, Anna ;
Cirrincione, Girolamo ;
Viola, Giampietro ;
Salvador, Alessia ;
Vedaldi, Daniela ;
Dall'Acqua, Francesco .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (22) :9668-9683
[4]   Novel carbazole and acyl-indole antimitotics [J].
Barta, Thomas E. ;
Barabasz, Amy F. ;
Foley, Briana E. ;
Geng, Lifeng ;
Hall, Steven E. ;
Hanson, Gunnar J. ;
Jenks, Matthew ;
Ma, Wei ;
Rice, John W. ;
Veal, James .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (11) :3078-3080
[5]   Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes [J].
Chen, Weiliang ;
Cai, Yunfei ;
Fu, Xuan ;
Liu, Xiaohua ;
Lin, Lili ;
Feng, Xiaoming .
ORGANIC LETTERS, 2011, 13 (18) :4910-4913
[6]   Selective Synthesis of Acenaphtho[1,2-b]indole Derivatives via Tandem Regioselective Aza-Ene Addition/N-Cyclization/SN1 Type Reaction [J].
Chen, Xue-Bing ;
Luo, Ting-Bi ;
Gou, Gao-Zhang ;
Wang, Jing ;
Liu, Wei ;
Lin, Jun .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (09) :921-928
[7]   Discovery of Pyrrole-Indoline-2-ones as Aurora Kinase Inhibitors with a Different Inhibition Profile [J].
Chiang, Chao-Cheng ;
Lin, Yu-Hsiang ;
Lin, Shu Fu ;
Lai, Chun-Liang ;
Liu, Chiawei ;
Wei, Win-Yin ;
Yang, Sheng-chuan ;
Wane, Ru-Wen ;
Teng, Li-Wei ;
Chuang, Shih-Hsien ;
Chang, Jia-Ming ;
Yuan, Ta-Tung ;
Lee, Ying-Shuen ;
Chen, Paonien ;
Chi, Wei-Kuang ;
Yang, Ju-Ying ;
Huang, Hung-Jyun ;
Liao, Chu-Bin ;
Huang, Jiann-Jyh .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (16) :5929-5941
[8]   Synthesis of new trifluoromethylated indole derivatives [J].
Darehkordi, Ali ;
Rahmani, Fariba ;
Hashemi, Vahide .
TETRAHEDRON LETTERS, 2013, 54 (35) :4689-4692
[9]   Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system [J].
England, Dylan B. ;
Merey, Gokce ;
Padwa, Albert .
ORGANIC LETTERS, 2007, 9 (19) :3805-3807
[10]   Unprecedented Bridged Annulation Approach to the Construction of 5,6-Dihydro-4H-benzo[kl]acridines [J].
Goel, Atul ;
Singh, Salil Pratap ;
Kumar, Amit ;
Kant, Ruchir ;
Maulik, Prakas R. .
ORGANIC LETTERS, 2009, 11 (22) :5122-5125