A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

Scholarly Works

• Ganesan, P.; Ranganathan, R.; Vijay Solomon, R.; Muhamed Noorani, P.; Ganesan, P.; Thajuddin, N.; Venkattappan, A.; Rajalingam, R.; Gao, P. Unravelling the Optoelectronic and Biological Properties of Phenanthroimidazo [1,2‐c] Quinazoline‐Based Donor‐Acceptor Materials. Asian Journal of Organic Chemistry 2024. doi:10.1002/ajoc.202400285
• Bairy, G.; Sinha, C. An Extensive Analysis of Current Synthetic Methodologies and Applications of Imidazo/Benzimidazo[1,2‐c]Quinazolines. ChemistrySelect 2024, 9. doi:10.1002/slct.202400421
• Nandwana, N. K.; Patel, O. P. S.; Mehra, M. K.; Kumar, A.; Salvino, J. M. Recent Advances in Metal-Catalyzed Approaches for the Synthesis of Quinazoline Derivatives. Molecules (Basel, Switzerland) 2024, 29, 2353. doi:10.3390/molecules29102353
• Rafiq, A.; Aslam, S.; Ahmad, M.; Jawwad Saif, M.; A. Al-Hussain, S.; E.A. Zaki, M. Recent Approaches for the Synthesis of Imidazoquinazolines and Benzimidazoquinazolines. Recent Advances on Quinazoline; IntechOpen, 2023. doi:10.5772/intechopen.1001896
• Yang, M.-L.; Zhao, L.; Chen, H.-R.; Ding, M.-W. Stereoselective Synthesis of 12-Tetrazolyl Substituted (E)-5H-Quinazolino[3,2-a]quinazolines via Sequential Ugi-Azide/Staudinger/aza-Wittig/Addition/Ag(I)-Catalyzed Cyclization. The Journal of organic chemistry 2023, 88, 1898–1906. doi:10.1021/acs.joc.2c02621
• Xiaojing, T.; Zhenzhen, F.; Si, J.; Zhiwei, L.; Jiangsheng, L.; Yuefei, Z.; Cuihong, L.; Weidong, L. Metal-Free Synthesis of Benzimidazo[1,2-c]quinazolines from N-Cyanobenzimidazoles via Double C—H Functionalizations. Chinese Journal of Organic Chemistry 2022, 42, 3684. doi:10.6023/cjoc202205030
• Seifinoferest, B.; Tanbakouchian, A.; Larijani, B.; Mahdavi, M. Ullmann-Goldberg and Buchwald-Hartwig C−N Cross Couplings: Synthetic Methods to Pharmaceutically Potential N-Heterocycles. Asian Journal of Organic Chemistry 2021, 10, 1319–1344. doi:10.1002/ajoc.202100072
• Yamamoto, Y. Copper-mediated synthesis of quinazolines and related benzodiazines. Copper in N-Heterocyclic Chemistry; Elsevier, 2021; pp 289–331. doi:10.1016/b978-0-12-821263-9.00008-4
• Pang, X.; Zhao, H.; Ma, S. A Microfluidics Reaction System with Automation for a Multicomponent Reaction. Advanced Intelligent Systems 2020, 2, 1900191. doi:10.1002/aisy.201900191
• Hussen, A. S.; Bagchi, S.; Sharma, A. Ammonium Chloride Assisted Microwave Mediated Domino Multicomponent Reaction: An Efficient and Sustainable Synthesis of Quinazolin-4(3H)-imines under Solvent Free Condition. ChemistrySelect 2019, 4, 10169–10173. doi:10.1002/slct.201900923
• Rodrigues, R.; Tran, L. Q.; Darses, B.; Dauban, P.; Neuville, L. Copper‐Promoted Tandem Three‐Component Access to Quinazolin‐4(H)‐imines and Benzimidazo[1,2‐c]quinazolines. Advanced Synthesis & Catalysis 2019, 361, 4454–4460. doi:10.1002/adsc.201900658
• Sandeep, K.; Reddy, A. S.; Swamy, K. C. K. Cu(i) catalysed annulation of isothiocyanates/isocyanates with 2-iodo-sulfonamides: synthesis of benzodithiazines, benzothiadiazinones, benzothiazinylidene-anilines and benzothiazolylidene-anilines. Organic & biomolecular chemistry 2019, 17, 6880–6894. doi:10.1039/c9ob00994a
• Dai, Z.; Li, S. C.; Li, Y.; Feng, L.; Ma, C. Metal-free synthesis of benzimidazo[1,2-c]quinazolin-6-ones with indole and benzenediamine oxidized by I2/TBHP. Tetrahedron 2019, 75, 2012–2017. doi:10.1016/j.tet.2019.02.022
• Villo, P.; Olofsson, B. PATAI'S Chemistry of Functional Groups - Arylations Promoted by Hypervalent Iodine Reagents. Patai's Chemistry of Functional Groups 2018, 1–61. doi:10.1002/9780470682531.pat0950
• Jianghe, Z.; Shao, Y.; Hu, K.; Linjun, Q.; Cheng, T.; Chen, J. Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines. Organic & biomolecular chemistry 2018, 16, 8596–8603. doi:10.1039/c8ob02421a
• Ambethkar, S.; Kalaiselvi, M.; Ramamoorthy, J.; Padmini, V. I2-Catalyzed Oxidative Cross-Coupling Reaction of Methyl Ketones and 2-(2-Aminophenyl) Benzimidazole: Facile Access to Benzimidazo[1,2-c]quinazoline. ACS omega 2018, 3, 5021–5028. doi:10.1021/acsomega.8b00067
• Wu, X.; Sun, S.; Xu, S.; Cheng, J. Rh‐Catalyzed Annulation of ortho‐C−H Bonds of 2‐Arylimidazoles with 1,4,2‐Dioxazol‐5‐ones toward 5‐Arylimidazo[1,2‐c]quinazolines. Advanced Synthesis & Catalysis 2018, 360, 1111–1115. doi:10.1002/adsc.201701331
• Shinde, A. H.; Arepally, S.; Baravkar, M. D.; Sharada, D. S. Nickel-Catalyzed Aerobic Oxidative Isocyanide Insertion: Access to Benzimidazoquinazoline Derivatives via a Sequential Double Annulation Cascade (SDAC) Strategy. The Journal of organic chemistry 2016, 82, 331–342. doi:10.1021/acs.joc.6b02423
• Khan, I.; Zaib, S.; Batool, S.; Abbas, N.; Ashraf, Z.; Iqbal, J.; Saeed, A. Quinazolines and quinazolinones as ubiquitous structural fragments in medicinal chemistry: An update on the development of synthetic methods and pharmacological diversification. Bioorganic & medicinal chemistry 2016, 24, 2361–2381. doi:10.1016/j.bmc.2016.03.031
• Pang, X.; Chen, C.; Li, M.; Xi, C. A Concise and Efficient Synthesis of Benzimidazo[1,2-c]quinazolines Through CuI-Catalyzed Intramolecular N-Arylations. ChemInform 2016, 47. doi:10.1002/chin.201610189

Explore citations to this article at