Citation: Hossein Mehrabi, Mahdi Hatami-Pour. Facile, one-pot synthesis of new phenanthridine derivatives through 1,4-dipolar cycloaddition of phenantridine, activated acetylenes, and aromatic aldehydes[J]. Chinese Chemical Letters, ;2014, 25(11): 1495-1498. doi: 10.1016/j.cclet.2014.05.024
-
A facile, one-pot synthesis of new phenanthridine derivatives by a three-component reaction between phenantridine, dialkyl acetylenedicarboxylates (DAADs), and aromatic aldehydes is described. The reaction is characterized by mild conditions, high selectivity, and tolerance to various functional groups.
-
-
[1]
[1] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
-
[2]
[2] A. Dö mling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.
-
[3]
[3] M.A. Mironov, Design of multi-component reactions: from libraries of compounds to libraries of reactions, QSAR Comb. Sci. 25 (2006) 423-431.
-
[4]
[4] A. Padwa, S.K. Bur, The domino way to heterocycles, Tetrahedron 63 (2007) 5341- 5378.
-
[5]
[5] D. Marko, M.D. Mihovilovic, P. Stanetty, Metal-assisted multicomponent reactions involving carbon monoxide-towards heterocycle synthesis, Angew. Chem. Int. Ed. 46 (2007) 3612-3615.
-
[6]
[6] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidinesuccinates, Org. Lett. 3 (2001) 3495-3497.
-
[7]
[7] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidenesuccinates, Org. Lett. 4 (2002) 2807.
-
[8]
[8] V. Nair, A.R. Sreekanth, N. Abhilash, M.M. Bhadbhade, R.C. Gonnade, A novel threecomponent reaction for the diastereoselective synthesis of 2H-pyrimido[2,1- a]isoquinolines via 1,4-dipolar cycloaddition, Org. Lett. 4 (2002) 3575-3577.
-
[9]
[9] V. Nair, A.R. Sreekanth, A.T. Biju, N.P. Rath, The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2- and 1,4-benzoquinones: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines, Tetrahedron Lett. 44 (2003) 729-732.
-
[10]
[10] V. Nair, B.R. Devi, R.L. Varma, The Huisgen 1,4-dipolar cycloaddition involving isoquinoline, dimethyl butynedioate and activated styrenes: a facile synthesis of tetrahydrobenzoquinolizine derivatives, Tetrahedron Lett. 46 (2005) 5333-5335.
-
[11]
[11] V. Nair, C. Rajesh, A.U. Vinod, Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes, Acc. Chem. Res. 36 (2003) 899-907.
-
[12]
[12] V. Nair, R.S. Menon, A. Sreekanth, N. Abhilash, A.T. Biju, Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: a promising synthetic strategy, Acc. Chem. Res. 39 (2006) 520-530.
-
[13]
[13] M. Lei, Z.J. Zhan, W. Tian, P. Lu, One-pot, three-component synthesis of highly functionalized 1,3-oxazine derivatives from a,b-unsaturated imine, alkyne, and aldehyde, Tetrahedron 68 (2012) 3361-3367.
-
[14]
[14] V. Nair, S. Devipriya, E. Suresh, Efficient synthesis of [1,3]oxazino[2,3-a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline-DMAD zwitterion and carbonyl compounds, Tetrahedron Lett. 48 (2007) 3667-3670.
-
[15]
[15] H. Mehrabi, M.A. Hatami-Pour, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 43 (2013) 611-618.
-
[16]
[16] H. Mehrabi, J. Pishahang, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 44 (2014) 76-81.
-
[1]
-
-
[1]
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
-
[2]
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
-
[3]
Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
-
[4]
Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
-
[5]
Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
-
[6]
Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
-
[7]
Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
-
[8]
Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
-
[9]
Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
-
[10]
Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
-
[11]
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
-
[12]
Tingting Huang , Zhuanlong Ding , Hao Liu , Ping-An Chen , Longfeng Zhao , Yuanyuan Hu , Yifan Yao , Kun Yang , Zebing Zeng . Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties. Chinese Chemical Letters, 2024, 35(4): 109117-. doi: 10.1016/j.cclet.2023.109117
-
[13]
Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
-
[14]
Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
-
[15]
Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
-
[16]
Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
-
[17]
Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
-
[18]
Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
-
[19]
Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
-
[20]
Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(659)
- HTML views(2)