ACS Publications. Most Trusted. Most Cited. Most Read
Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
My Activity
    Letter

    Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
    Click to copy article linkArticle link copied!

    View Author Information
    Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
    University of Chinese Academy of Sciences, Beijing 100049, China
    Other Access OptionsSupporting Information (1)

    Organic Letters

    Cite this: Org. Lett. 2017, 19, 20, 5629–5632
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b02786
    Published October 2, 2017
    Copyright © 2017 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.

    Copyright © 2017 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b02786.

    • Experimental procedures, detailed characterization data of substrates, catalysts and products, and 1H and 13C NMR spectra (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 87 publications.

    1. Amreen K. Bains, Harshit Jain, Abhishek Kundu, Rahul Singh, Sudha Yadav, Yadav Ankit, Debashis Adhikari. Cofactor-Inspired Quinone Catalysis Following a One-Electron Hydrogen Atom Transfer Pathway. ACS Catalysis 2024, 14 (23) , 17993-18002. https://doi.org/10.1021/acscatal.4c05988
    2. Shaoqi Xiong, Jijun Pu, Tiebo Xiao, Yubo Jiang. Synthesis of 2,3-Diperfluoroalkylated Quinoxalines via Selenium-Catalyzed Reductive C–C Coupling of Vicinal Perfluoroalkyl Formimidoyl Chlorides. Organic Letters 2024, 26 (41) , 8866-8871. https://doi.org/10.1021/acs.orglett.4c03308
    3. Nittan Singh, Suresh Babu Putla, Chandrodai Pratap Singh, Pavan Narayan Kalbande, Priyanka Choudhary, Sailaja Krishnamurty, Venkata Krishnan, Kushal Bhatte, Putla Sudarsanam. Shape-Controlled MoO3/MnOx Nanocatalyst for the Selective Synthesis of 2-Phenylquinoxaline Drug Motifs. ACS Applied Nano Materials 2023, 6 (24) , 23442-23453. https://doi.org/10.1021/acsanm.3c04820
    4. Mahdieh Esi Firuz, Saideh Rajai-Daryasarei, Frank Rominger, Abbas Biglari, Saeed Balalaie. Mn-Mediated Direct Regioselective C–H Trifluoromethylation of Imidazopyridines and Quinoxalines. The Journal of Organic Chemistry 2023, 88 (15) , 10599-10608. https://doi.org/10.1021/acs.joc.3c00621
    5. Sophie A. Fitzgerald, Haleema Y. Otaif, Christopher E. Elgar, Natalia Sawicka, Peter N. Horton, Simon J. Coles, Joseph M. Beames, Simon J. A. Pope. Polysubstituted Ligand Framework for Color Tuning Phosphorescent Iridium(III) Complexes. Inorganic Chemistry 2021, 60 (20) , 15467-15484. https://doi.org/10.1021/acs.inorgchem.1c02121
    6. Xinxin Qiao, Yong-De Zhao, Mingru Rao, Zhan-Wei Bu, Guangwu Zhang, Heng-Ying Xiong. Delivering 2-Aryl Benzoxazoles through Metal-Free and Redox-Neutral De-CF3 Process. The Journal of Organic Chemistry 2021, 86 (19) , 13548-13558. https://doi.org/10.1021/acs.joc.1c01619
    7. Hashem Sharghi, Mina Aali Hosseini, Jasem Aboonajmi, Mahdi Aberi. Use of Vitamin B12 as a Nontoxic and Natural Catalyst for the Synthesis of Benzoxazoles via Catechols and Primary Amines in Water under Aerobic Oxidation. ACS Sustainable Chemistry & Engineering 2021, 9 (33) , 11163-11170. https://doi.org/10.1021/acssuschemeng.1c03152
    8. Amreen K. Bains, Yadav Ankit, Debashis Adhikari. Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions. Organic Letters 2021, 23 (6) , 2019-2023. https://doi.org/10.1021/acs.orglett.1c00162
    9. James Levi Knippel, Yuxuan Ye, Stephen L. Buchwald. Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles. Organic Letters 2021, 23 (6) , 2153-2157. https://doi.org/10.1021/acs.orglett.1c00306
    10. Pradip Ramdas Thorve, Biplab Maji. Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst. Organic Letters 2021, 23 (2) , 542-547. https://doi.org/10.1021/acs.orglett.0c04060
    11. Shruti Dadwal, Manoj Kumar, Vandana Bhalla. “Metal-Free” Nanoassemblies of AIEE-ICT-Active Pyrazine Derivative: Efficient Photoredox System for the Synthesis of Benzimidazoles. The Journal of Organic Chemistry 2020, 85 (21) , 13906-13919. https://doi.org/10.1021/acs.joc.0c01965
    12. Dineshkumar Raja, Abigail Philips, Pushbaraj Palani, Wei-Yu Lin, Sundaramurthy Devikala, Gopal Chandru Senadi. Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d-Glucose with o-Phenylenediamines in Water. The Journal of Organic Chemistry 2020, 85 (17) , 11531-11540. https://doi.org/10.1021/acs.joc.0c01053
    13. Hashem Sharghi, Jasem Aboonajmi, Mahdi Aberi. One-Pot Multicomponent Reaction of Catechols, Ammonium Acetate, and Aldehydes for the Synthesis of Benzoxazole Derivatives Using the Fe(III)–Salen Complex. The Journal of Organic Chemistry 2020, 85 (10) , 6567-6577. https://doi.org/10.1021/acs.joc.0c00560
    14. Pawan Thapa, Philip M. Palacios, Tam Tran, Brad S. Pierce, Frank W. Foss, Jr.. 1,2-Disubstituted Benzimidazoles by the Iron Catalyzed Cross-Dehydrogenative Coupling of Isomeric o-Phenylenediamine Substrates. The Journal of Organic Chemistry 2020, 85 (4) , 1991-2009. https://doi.org/10.1021/acs.joc.9b02714
    15. Tengda Si, Hun Young Kim, Kyungsoo Oh. Substrate Promiscuity of ortho-Naphthoquinone Catalyst: Catalytic Aerobic Amine Oxidation Protocols to Deaminative Cross-Coupling and N-Nitrosation. ACS Catalysis 2019, 9 (10) , 9216-9221. https://doi.org/10.1021/acscatal.9b03442
    16. Shweta A. Pawar, Ayushi N. Chand, A. Vijay Kumar. Polydopamine: An Amine Oxidase Mimicking Sustainable Catalyst for the Synthesis of Nitrogen Heterocycles under Aqueous Conditions. ACS Sustainable Chemistry & Engineering 2019, 7 (9) , 8274-8286. https://doi.org/10.1021/acssuschemeng.8b06677
    17. Ruipu Zhang, Yan Qin, Long Zhang, Sanzhong Luo. Mechanistic Studies on Bioinspired Aerobic C–H Oxidation of Amines with an ortho-Quinone Catalyst. The Journal of Organic Chemistry 2019, 84 (5) , 2542-2555. https://doi.org/10.1021/acs.joc.8b02948
    18. Yi Tao, Jiahui Zhang, Yangyang Hu, Huiying Liu, Jingwen Sun, Lei Liu. Electrosynthesis of Quinoxalines via Intermolecular Cyclization/Dehydrogenation of Ketones with o-Phenylenediamines. Synlett 2025, 36 (04) , 383-388. https://doi.org/10.1055/a-2339-2832
    19. Jayaveerapandiyan Barathkumar, Rohan Gupta, Subbiah Nagarajan. Recent Developments in the Photochemical Reactions of N‐Heterocyclic Compounds. European Journal of Organic Chemistry 2024, 27 (48) https://doi.org/10.1002/ejoc.202401195
    20. Yongsheng Zhou, Yue Zhang, Xiaojiao Du, Jian Li, Chunping Dong. Aerobic Oxidative Synthesis of N ‐Containing Heterocycles from o ‐Substituted Aniline Derivatives and Primary Amines by Perylene Diimide Catalysis. European Journal of Organic Chemistry 2024, 27 (44) https://doi.org/10.1002/ejoc.202400631
    21. Shweta A. Pawar, Sanket Gije, Chinmay Kalantre, V. H. Dalvi, A. Vijay Kumar. Sodium Copper Chlorophyllin: A Sustainable Bioinspired Catalyst for the Aerobic Oxidative Synthesis of Nitrogen Heterocycles and the Oxidative Cyanation of Tertiary Amines. ChemistrySelect 2024, 9 (41) https://doi.org/10.1002/slct.202402931
    22. Feifei Wang, Zhiyong Yang, Jiaqi Yan, Qiuyan Xue. Direct Arylation of Benzoxazoles with Benzoyl Chlorides under Mild Conditions. European Journal of Organic Chemistry 2024, 27 (27) https://doi.org/10.1002/ejoc.202400303
    23. R. Bernadett Vlocskó, Manisha Mishra, A. Ioana Stoica, Leila Gustin, Béla Török. Catalyst-free synthesis of substituted benzimidazoles and benzothiazoles in a sustainable solvent. Tetrahedron Green Chem 2024, 3 , 100035. https://doi.org/10.1016/j.tgchem.2023.100035
    24. Sourav Behera, Shyamal Kanti Bera, Francesco Basoccu, Federico Cuccu, Pietro Caboni, Lidia De Luca, Andrea Porcheddu. Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation. Advanced Synthesis & Catalysis 2024, 366 (9) , 2035-2043. https://doi.org/10.1002/adsc.202301407
    25. Hue Thi Buu Bui, Kiep Minh Do, Quang Vinh Hong, Hieu Trong Le, Saw Yu Yu Hnin, De Quang Tran, Hieu Van Mai, Thao Thi Thach Nguyen, Trang Thi Kieu Mai, Hiroyuki Morita. Solvent-free strategy for facile synthesis and cytotoxicity evaluation of benzimidazole derivatives. Tetrahedron 2024, 156 , 133940. https://doi.org/10.1016/j.tet.2024.133940
    26. Salavat S. Ashirbaev, Natércia F. Brás, Patricia Frei, Kuangjie Liu, Simone Moser, Hendrik Zipse. Redox‐Mediated Amination of Pyrogallol‐Based Polyphenols. Chemistry – A European Journal 2024, 30 (12) https://doi.org/10.1002/chem.202303783
    27. Sheik Allavudeen Abdul Rahman, Chandrima N. Patra, Goutam Kumar Kole, Silda Peters, Tumpa Sadhukhan, Baburaj Baskar. Metal–organic framework-catalyzed selective oxidation of alcohols and oxidative cross-coupling for C–C and C–N bond-forming reactions. New Journal of Chemistry 2024, 48 (8) , 3513-3524. https://doi.org/10.1039/D3NJ05260E
    28. Soumyadip Das, Kaushik Chanda. One-Pot Telescopic Approach to Synthesize Disubstituted Benz­imidazoles in Deep Eutectic Solvent. Synthesis 2024, 56 (04) , 693-699. https://doi.org/10.1055/a-2102-1192
    29. Yuta Shiogai, Marina Oka, Hazuki Miyake, Hiroki Iida. Aerobic oxidative synthesis of benzimidazoles by flavin photocatalysis. Organic & Biomolecular Chemistry 2024, 120 https://doi.org/10.1039/D4OB00360H
    30. Hua Liu, Wen-Wen Yi, Quan-Quan Li, Shu-Ya Zhao. Visible-light-active benzothiadiazole-based MOFs as efficient ROS generators for the synthesis of benzimidazoles and benzothiazoles. Inorganic Chemistry Frontiers 2024, 7 https://doi.org/10.1039/D4QI01368A
    31. Runze Zhang, Long Zhang, Sanzhong Luo. Aerobic Organocatalytic Oxidation. 2024https://doi.org/10.1016/B978-0-323-96025-0.00129-0
    32. Khushbu Rajput, Vishal Singh, Arsala Kamal, Himanshu Kumar Singh, Sundaram Singh, Vandana Srivastava. A novel approach towards synthesis of benzothiazoles and benzimidazoles: Eosin Y-catalyzed photo-triggered C–S and C–N bond formation. New Journal of Chemistry 2023, 47 (48) , 22276-22280. https://doi.org/10.1039/D3NJ04374F
    33. Virendra Kumar Chaudhary, Sain Singh, Kapil Kumar, Angshuman R. Choudhury, Kaushik Ghosh. Facile synthesis of benzoxazole derivatives by a multi-component reaction catalysed by copper complexes capable of generating phenoxyl radical complex. New Journal of Chemistry 2023, 47 (41) , 18995-19004. https://doi.org/10.1039/D3NJ03160H
    34. Himanshu Singh, Rajnish Kumar, Prashant Tiwari, Ayushi Singh. Recent Advances in Synthetic Strategies of Benzimidazole and its Analogs: A Review. Current Organic Chemistry 2023, 26 (19) , 1767-1778. https://doi.org/10.2174/1385272827666221216113723
    35. Jasem Aboonajmi, Masoumeh Mohammadi, Farhad Panahi, Mahdi Aberi, Hashem Sharghi. One-pot, three-component, iron-catalyzed synthesis of benzimidazoles via domino C–N bond formation. RSC Advances 2023, 13 (35) , 24789-24794. https://doi.org/10.1039/D3RA04450E
    36. Shaik Firoj Basha, Yeruva Pavankumar Reddy, Poorna Chandrasekhar Settipalli, Tangella Nagendra Prasad, Vadiga Shanthi Kumar, Gajula Mahaboob Basha, Varimadugu Aruna, Naveen Mulakayala, Shaik Anwar. An Efficient Multi-Functionalized Synthesis of N-Arylated Indole-3- Substituted-2-Benzimidazoles as Anticancer Agents. Letters in Organic Chemistry 2023, 20 (8) , 701-710. https://doi.org/10.2174/1570178620666230217111458
    37. Ariprasanth Ramalingam, Gopal Chandru Senadi. Synthesis of Ni@C as a Magnetic Heterogeneous Catalyst: Application to Benzimidazoles and Quinoxalines from o ‐Phenylenediamines with Primary Amines. Asian Journal of Organic Chemistry 2023, 12 (7) https://doi.org/10.1002/ajoc.202300119
    38. G. Kavya, Ajil R. Nair, Akhil Sivan. An Insight into the Recent Synthetic Approaches of Benzimidazole Motifs Based on Divergent Substrate Scope. Mini-Reviews in Organic Chemistry 2023, 20 (4) , 333-357. https://doi.org/10.2174/1570193X19666220420134233
    39. Sophie A. Fitzgerald, Xiao Xiao, Jianzhang Zhao, Peter N. Horton, Simon J. Coles, Richard C. Knighton, Benjamin D. Ward, Simon J. A. Pope. Organometallic Platinum(II) Photosensitisers that Demonstrate Ligand‐Modulated Triplet‐Triplet Annihilation Energy Upconversion Efficiencies. Chemistry – A European Journal 2023, 29 (9) https://doi.org/10.1002/chem.202203241
    40. Pradip Ramdas Thorve, Kakoli Maji, Biplab Maji. Construction of 1,2,4-triazole-fused heterocycles via an amine oxidase-inspired catalyst. Organic Chemistry Frontiers 2023, 10 (2) , 480-489. https://doi.org/10.1039/D2QO01745H
    41. Pravin J. Wanjari, Nirjhar Saha, Gurudutt Dubey, Prasad V. Bharatam. Metal-free methods for the generation of benzimidazoles and 2-aminobenzimidazoles. Tetrahedron 2023, 130 , 133143. https://doi.org/10.1016/j.tet.2022.133143
    42. Ruipu Zhang, Runze Zhang, Ruijun Jian, Long Zhang, Ming-Tian Zhang, Yu Xia, Sanzhong Luo. Bio-inspired lanthanum-ortho-quinone catalysis for aerobic alcohol oxidation: semi-quinone anionic radical as redox ligand. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-28102-4
    43. Jasem Aboonajmi, Farhad Panahi, Mina Aali Hosseini, Mahdi Aberi, Hashem Sharghi. Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones via C–C and C–O bond cleavage. RSC Advances 2022, 12 (32) , 20968-20972. https://doi.org/10.1039/D2RA03340B
    44. Yuhuan Qin, Mingming Hao, Zhengxin Ding, Zhaohui Li. Pt@MIL-101(Fe) for efficient visible light initiated coproduction of benzimidazoles and hydrogen from the reaction between o-Phenylenediamines and alcohols. Journal of Catalysis 2022, 410 , 156-163. https://doi.org/10.1016/j.jcat.2022.04.023
    45. Shu-Ning Lu, Yue Sun, Jiajun Zhang, Zhengkai Chen, Xiao-Feng Wu. Metal-free Synthesis of 5-Trifluoromethyl-1,2,4-triazoles via elemental sulfur promoted oxidative cyclization of trifluoroacetimidohydrazides with benzylic and aliphatic amines. Molecular Catalysis 2022, 524 , 112336. https://doi.org/10.1016/j.mcat.2022.112336
    46. Muhammad Adnan Bashir, Langyu Tang, Longjie Li, Huaibin Yu, Weijun Yao, Guojiao Wu, Fangrui Zhong. Formal dual C(sp 2 )–H cross-dehydrogenative C–O bond formation to construct highly functionalized diaryl ethers with O 2. Organic Chemistry Frontiers 2022, 9 (8) , 2249-2255. https://doi.org/10.1039/D1QO01942B
    47. Sajjad Oliaei, Davood Habibi, Somayyeh Heydari, Roya Karamian, Nika Ranjbar. Design, preparation, biological investigations and application of a benzoguanamine-based nickel complex for the synthesis of benzimidazoles. Journal of Molecular Structure 2022, 1254 , 132328. https://doi.org/10.1016/j.molstruc.2022.132328
    48. Santu Sadhukhan, Swagata Mondal, Beeraiah Baire. An Unexpected Formation of 2‐Arylbenzimidazoles from α,α‐Diiodo‐α’‐acetoxyketones and o ‐Phenylenediamines. European Journal of Organic Chemistry 2022, 2022 (6) https://doi.org/10.1002/ejoc.202101375
    49. Ming Yang, Xue-Cen Xu, Yue Gong, Yu-Long Zhao. Rhodium-catalyzed coupling-cyclization reaction of isocyanides and 2-azidophenyloxyacrylates: synthesis of N -(3-substituted benzo[ d ]oxazol-2(3 H )-ylidene)amines and dihydrobenzo[ d ]oxazoles. Organic Chemistry Frontiers 2022, 9 (2) , 407-412. https://doi.org/10.1039/D1QO01506K
    50. G. Varvounis, V. Gkalpinos, P. Theodorakopoulou, E. Tsemperlidou. Imidazoles. 2022, 113-307. https://doi.org/10.1016/B978-0-12-818655-8.00140-2
    51. Dheeraj Singh Chauhan, F. El-Hajjaji, M.A. Quraishi. Heterocyclic ionic liquids as environmentally benign corrosion inhibitors: recent advances and future perspectives. 2022, 279-294. https://doi.org/10.1016/B978-0-12-824545-3.00018-0
    52. Yadong Li, Pengju Wu, Zhiyong Yang. Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α -Ketoic Acids by Photoredox Catalysis. Chinese Journal of Organic Chemistry 2022, 42 (6) , 1770. https://doi.org/10.6023/cjoc202110030
    53. Gaurav Badhani, Abhisek Joshi, Subbarayappa Adimurthy. Ionic‐Liquid‐Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C−N, C−S, and C−C Bond Formation. European Journal of Organic Chemistry 2021, 2021 (48) , 6705-6716. https://doi.org/10.1002/ejoc.202101135
    54. Kuppalli R. Kiran, Toreshettahally R. Swaroop, Chikkappaiahnayaka Santhosh, Kanchugarakoppal S. Rangappa, Maralinganadoddi P. Sadashiva. Cyclocondensation of o ‐Phenylenediamines with 2‐Oxo‐ethanimidothioates: A Novel Synthesis of 2‐Amino‐3‐(het)aryl‐quinoxalines. ChemistrySelect 2021, 6 (29) , 7262-7265. https://doi.org/10.1002/slct.202102071
    55. Yuhuan Qin, Mingming Hao, Chao Xu, Zhaohui Li. Visible light initiated oxidative coupling of alcohols and o -phenylenediamines to synthesize benzimidazoles over MIL-101(Fe) promoted by plasmonic Au. Green Chemistry 2021, 23 (11) , 4161-4169. https://doi.org/10.1039/D1GC01047F
    56. M.A. Quraishi, Dheeraj Singh Chauhan, Farhat A. Ansari. Development of environmentally benign corrosion inhibitors for organic acid environments for oil-gas industry. Journal of Molecular Liquids 2021, 329 , 115514. https://doi.org/10.1016/j.molliq.2021.115514
    57. Yuxin Ding, Renchao Ma, Yongmin Ma. Solvent-dependent metal-free chemoselective synthesis of benzimidazoles and 1,3,5-triarylbenzenes from 2-amino anilines and aryl alkyl ketones catalyzed by I2. Tetrahedron Letters 2021, 70 , 153016. https://doi.org/10.1016/j.tetlet.2021.153016
    58. Pradip Ramdas Thorve, Biplab Maji. Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst. Catalysis Science & Technology 2021, 11 (3) , 1116-1124. https://doi.org/10.1039/D0CY01764G
    59. Wan-Kai An, Shi-Jia Zheng, Hui-Xing Zhang, Tian-Tian Shang, He-Rui Wang, Xiao-Jing Xu, Qiu Jin, Yuchen Qin, Yunlai Ren, Song Jiang, Cui-Lian Xu, Mao-Song Hou, Zhenliang Pan. s -Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles. Green Chemistry 2021, 23 (3) , 1292-1299. https://doi.org/10.1039/D0GC03719B
    60. Jhonny Azuaje, Adrián Rama, Ana Mallo-Abreu, Mónica G. Boado, María Majellaro, Carmen R. Tubío, Rubén Prieto, Xerardo García-Mera, Francisco Guitián, Eddy Sotelo, Alvaro Gil. Catalytic performance of a metal-free graphene oxide-Al2O3 composite assembled by 3D printing. Journal of the European Ceramic Society 2021, 41 (2) , 1399-1406. https://doi.org/10.1016/j.jeurceramsoc.2020.10.010
    61. Vu Thanh Nguyen, Hai Truong Nguyen, Phuong Hoang Tran. One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight. New Journal of Chemistry 2021, 45 (4) , 2053-2059. https://doi.org/10.1039/D0NJ05687A
    62. Elpida Skolia, Mary K. Apostolopoulou, Nikolaos F. Nikitas, Christoforos G. Kokotos. Photochemical Synthesis of Benzimidazoles from Diamines and Aldehydes. European Journal of Organic Chemistry 2021, 2021 (3) , 422-428. https://doi.org/10.1002/ejoc.202001357
    63. Kathleen J. Berger, Mark D. Levin. Reframing primary alkyl amines as aliphatic building blocks. Organic & Biomolecular Chemistry 2021, 19 (1) , 11-36. https://doi.org/10.1039/D0OB01807D
    64. Prasun Choudhury, Basudeb Basu. Green synthetic approaches towards benzimidazole and quinoxaline scaffolds. 2021, 689-768. https://doi.org/10.1016/B978-0-12-820792-5.00012-3
    65. Dheeraj Singh Chauhan, Priyanka Singh, M.A. Quraishi. Quinoxaline derivatives as efficient corrosion inhibitors: Current status, challenges and future perspectives. Journal of Molecular Liquids 2020, 320 , 114387. https://doi.org/10.1016/j.molliq.2020.114387
    66. Ran An, Mengbi Guo, Yingbo Zang, Hang Xu, Zhuang Hou, Chun Guo. Recent Advances in Synthesis of Benzazoles via Imines. Current Organic Chemistry 2020, 24 (17) , 1897-1942. https://doi.org/10.2174/1385272824999200818180845
    67. Guodong Shen, Zeyou Wang, Xianqiang Huang, Shuwen Gong, Jiangong Zhang, Zhenfei Tang, Manman Sun, Xin Lv. Bonded- and discreted-Lindqvist hexatungstate-based copper hybrids as heterogeneous catalysts for the one-pot synthesis of 2-phenylquinoxalines via 2-haloanilines with vinyl azides or 3-phenyl-2 H -azirines. Dalton Transactions 2020, 49 (40) , 13993-13998. https://doi.org/10.1039/D0DT02625E
    68. Zhenzhen Geng, Hong-yu Zhang, Guohui Yin, Yuecheng Zhang, Jiquan Zhao. A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o -phenylenediamines catalyzed by [MIMPs] + Cl - /NaNO 2 /TEMPO. Journal of Chemical Research 2020, 44 (9-10) , 557-565. https://doi.org/10.1177/1747519820912163
    69. Martine Largeron, Patrick Deschamps, Karim Hammad, Maurice-Bernard Fleury. A dual biomimetic process for the selective aerobic oxidative coupling of primary amines using pyrogallol as a precatalyst. Isolation of the [5 + 2] cycloaddition redox intermediates. Green Chemistry 2020, 22 (6) , 1894-1905. https://doi.org/10.1039/C9GC03992A
    70. Martine Largeron. Aerobic catalytic systems inspired by copper amine oxidases. Pure and Applied Chemistry 2020, 92 (2) , 233-242. https://doi.org/10.1515/pac-2019-0107
    71. Zhen-Hua Li, Xiao-Meng Sun, Jin-Jing Qin, Zhi-Yong Tan, Wen-Biao Wang, Yao Ma. Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes. Tetrahedron 2020, 76 (8) , 130945. https://doi.org/10.1016/j.tet.2020.130945
    72. Hanan A. Mohamed, Mohammad Hayal Alotaibi, Benson M. Kariuki, Gamal A. El-Hiti. Convenient Synthesis of New Heterocycles Containing the Quinoxaline Ring System. Letters in Organic Chemistry 2020, 17 (2) , 121-126. https://doi.org/10.2174/1570178616666190311161505
    73. Bailu Ge, Yanling Peng, Jing Liu, Si Wen, Cheng Peng, Guolin Cheng. Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles. Tetrahedron 2020, 76 (2) , 130818. https://doi.org/10.1016/j.tet.2019.130818
    74. Altab Shaikh, Owk Ravi, S. Pushpa Ragini, Nimma Sadhana, Surendar Reddy Bathula. Benzimidazoles and benzothiazoles from styrenes and N-vinylimidazole via palladium catalysed oxidative C C and C N bond cleavage. Tetrahedron Letters 2020, 61 (1) , 151356. https://doi.org/10.1016/j.tetlet.2019.151356
    75. Zhiyong Yang, Liang Zhou, Ying Liu, Hongwen Lu, Fengxuan Wu, Yuxin Xie, Jianle Liu. Base‐Promoted Metal‐Free Arylation of Benzoxazoles with Phenylglyoxylic Acids. ChemistrySelect 2019, 4 (47) , 13788-13791. https://doi.org/10.1002/slct.201903641
    76. Ute Wild, Olaf Hübner, Hans‐Jörg Himmel. Redox‐Active Guanidines in Proton‐Coupled Electron‐Transfer Reactions: Real Alternatives to Benzoquinones?. Chemistry – A European Journal 2019, 25 (70) , 15988-15992. https://doi.org/10.1002/chem.201903438
    77. Santanu Ghosh, Chandan K. Jana. Metal free biomimetic deaminative direct C–C coupling of unprotected primary amines with active methylene compounds. Organic & Biomolecular Chemistry 2019, 17 (48) , 10153-10157. https://doi.org/10.1039/C9OB02163A
    78. Qing Yang, Yilin Zhang, Wei Zeng, Zheng-Chao Duan, Xinxin Sang, Dawei Wang. Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines. Green Chemistry 2019, 21 (20) , 5683-5690. https://doi.org/10.1039/C9GC02409C
    79. Jinli Zhang, Mengjun Qiao, Ling Chen, Yibo Dong, Chengkang Jiao, Shengqi Liao, Yangjie Wu. Thiol substrate-promoted dehydrogenative cyclization of arylmethyl thiols with ortho -substituted amines: a universal approach to heteroaromatic compounds. Organic Chemistry Frontiers 2019, 6 (16) , 2844-2849. https://doi.org/10.1039/C9QO00554D
    80. Zhuofei Li, He Song, Rui Guo, Minghui Zuo, Chuanfu Hou, Shouneng Sun, Xin He, Zhizhong Sun, Wenyi Chu. Visible-light-induced condensation cyclization to synthesize benzimidazoles using fluorescein as a photocatalyst. Green Chemistry 2019, 21 (13) , 3602-3605. https://doi.org/10.1039/C9GC01359H
    81. Zhenzhen Zhan, Haojie Ma, Xinfeng Cui, Pengbo Jiang, Jinghong Pu, Yixin Zhang, Guosheng Huang. Selective synthesis of (1 H -benzo[ d ]imidazol-2-yl)(phenyl)methanone and quinoxaline from aromatic aldehyde and o -phenylenediamine. Organic & Biomolecular Chemistry 2019, 17 (20) , 5148-5152. https://doi.org/10.1039/C9OB00531E
    82. Kaushik Chakrabarti, Milan Maji, Sabuj Kundu. Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water. Green Chemistry 2019, 21 (8) , 1999-2004. https://doi.org/10.1039/C8GC03744B
    83. Ahmad A. Almasalma, Esteban Mejía. Mechanistic Pathways Toward the Synthesis of Heterocycles Under Cross-Dehydrogenative Conditions. 2019, 329-356. https://doi.org/10.1007/978-981-13-9144-6_10
    84. Mastaneh Shariati, Amin Rostami, Gholamhassan Imanzadeh, Somayyeh Kheirjou. Enzymatic regeneration of DDQ in aerobic oxidation of sulfides and oxidative coupling of thiols: New bioinspired cooperative catalytic system. Molecular Catalysis 2018, 461 , 48-53. https://doi.org/10.1016/j.mcat.2018.09.012
    85. Jinghong Pu, Xingxing Liu, Xinliang Luo, Zhenzhen Zhan, Yixin Zhang, Guosheng Huang. Metal‐Free Synthesis of the Functionalized Quinoxalines via α ‐Aminocarbonyl Compounds with o ‐Phenylenediamine. ChemistrySelect 2018, 3 (43) , 12219-12222. https://doi.org/10.1002/slct.201802735
    86. Ruipu Zhang, Sanzhong Luo. Bio-inspired quinone catalysis. Chinese Chemical Letters 2018, 29 (8) , 1193-1200. https://doi.org/10.1016/j.cclet.2018.02.009
    87. Qianqian Guan, Qi Sun, Lixian Wen, Zhenggen Zha, Yu Yang, Zhiyong Wang. The synthesis of benzimidazoles via a recycled palladium catalysed hydrogen transfer under mild conditions. Organic & Biomolecular Chemistry 2018, 16 (12) , 2088-2096. https://doi.org/10.1039/C8OB00323H

    Organic Letters

    Cite this: Org. Lett. 2017, 19, 20, 5629–5632
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b02786
    Published October 2, 2017
    Copyright © 2017 American Chemical Society

    Article Views

    4180

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.