Photochemical Synthesis of Benzimidazoles from Diamines and Aldehydes

被引：28
作者：
Skolia, Elpida [1 ]
Apostolopoulou, Mary K. [1 ]
Nikitas, Nikolaos F. [1 ]
Kokotos, Christoforos G. [1 ]
机构：
[1] Natl & Kapodistrian Univ Athens, Lab Organ Chem, Dept Chem, Athens 15771, Greece
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 03期
关键词：
Aldehydes; Benzimidazoles; Diamines; Green Chemistry; HAT; Photochemistry; ONE-POT SYNTHESIS; C-H ACTIVATION; MEDIATED TANDEM REACTION; ANTHELMINTIC AGENTS; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; ALPHA-ALKYLATION; PHASE SYNTHESIS; BOND FORMATION; DNA-BINDING;
D O I：
10.1002/ejoc.202001357
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, green, cheap, and metal-free photochemical protocol for the synthesis of benzimidazoles has been developed. 2,2-Dimethoxy-2-phenylacetophenone was employed as the photoinitiator and CFL lamps were used as the light source, leading to the cyclization of substituted diamines with aldehydes. The corresponding benzimidazoles were obtained in good to high yields. Mechanistic studies were conducted, in order to determine a plausible mechanism for the reaction.
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页码：422 / 428
页数：7
相关论文
共 134 条
[1]  
A L ADENBURG., 1875, Ber, V8, P677, DOI [10.1002/cber.187500801209, DOI 10.1002/CBER.187500801209]
[2]   Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C-H Functionalization and C-O/S Bond Formation [J].
Alla, Santhosh Kumar ;
Sadhu, Pradeep ;
Punniyamurthy, Tharmalingam .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7502-7511
[3]   Iodobenzene Catalyzed C-H Amination of N-Substituted Amidines Using m-Chloroperbenzoic Acid [J].
Alla, Santhosh Kumar ;
Kumar, Rapolu Kiran ;
Sadhu, Pradeep ;
Punniyamurthy, Tharmalingam .
ORGANIC LETTERS, 2013, 15 (06) :1334-1337
[4]   Thiophene-embedded conjugated microporous polymers for photocatalysis [J].
An, Wan-Kai ;
Zheng, Shi-Jia ;
Du, Ya-Nan ;
Ding, San-Yuan ;
Li, Zhi-Jun ;
Jiang, Song ;
Qin, Yuchen ;
Liu, Xiaobiao ;
Wei, Pi-Feng ;
Cao, Zhan-Qi ;
Song, Meirong ;
Pan, Zhenliang .
CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (15) :5171-5180
[5]  
[Anonymous], 2007, ANGEW CHEM, V119, P2652
[6]  
[Anonymous], 2008, ANGEW CHEM
[7]  
Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]
[8]   A short synthesis of the PARP inhibitor 2-(4-trifluoromethylphenyl)benzimidazole-4-carboxamide (NU1077) [J].
Austen, SC ;
Kane, JM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) :979-980
[9]  
Avinash P., 2008, Rasayan J. Chem, V1, P447
[10]   Mechanism of the Stereoselective α-Alkylation of Aldehydes Driven by the Photochemical Activity of Enamines [J].
Bahamonde, Ana ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (25) :8019-8030
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