Tổng hợp dẫn xuất 2-Benzimidazolyl-4-oxo-4H-Quinolizine bằng phương pháp hỗ trợ vi sóng
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Abstract
A rapid and efficient microwave-assisted synthetic method for the preparation of 2-benzimidazolyl-4-oxo-4H-quinolizine derivatives has been successfully developed. Three 2-(1H-benzimidazol-2-yl)-4H-quinolizin-4-one derivatives were obtained from the reaction between 4-oxo-4H-quinolizine-2-carbaldehyde and ortho-phenylenediamine or ortho-nitroaniline derivatives in the presence of Na2S2O4 or Na2S2O5 as oxidative agents. In all cases, good yields (76-92%) and short reaction time (10 minutes) were observed. The structures of these new 2-(1H-benzimidazol-2-yl)-4H-quinolizin-4-one derivatives were confirmed by 1H-NMR, 13C-NMR and MS spectra
Tóm tắt
Phương pháp nhanh chóng và hiệu quả ứng dụng sự hỗ trợ của vi sóng đã được phát triển thành công để tổng hợp các dẫn xuất 2-benzimidazolyl-4-oxo-4H quinolizine. Bằng phương pháp này, ba dẫn xuất 2-(1H-benzimidazol-2-yl)-4H-quinolizin-4-one đã được tổng hợp từ 4-oxo-4H-quinolizine-2-carbaldehyde với các ortho-phenylenediamine hoặc ortho-nitroaniline sử dụng Na2S2O4 hoặc Na2S2O5 làm tác nhân oxy hóa. Trong cả ba trường hợp khảo sát đều cho hiệu suất tổng hợp cao (76-92%) và thời gian tổng hợp ngắn (tối đa 10 phút). Cấu trúc của các dẫn xuất 2-(1H-benzimidazol-2-yl)-4H-quinolizin-4-one mới được xác định bằng các phương pháp phổ nghiệm 1H-NMR, 13C-NMR và MS.
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A. A. Farahat, E. Paliakov and A. Kumaretal, 2011, “Exploration of larger central ring linkers in furamidine analogues: synthesis and evaluation of their DNA binding, antiparasitic and luorescence properties”. Bioorganic & Medicinal Chemistry, Vol. 19, no. 7, pp. 2156–2167.
A. Abdel-monem, 2007. Arch. Pharm. Res., 30, 678.
A. Chimirri, A. D. Sarro, G. D. Sarro, R. Gitto and M. Zappala, 2001. Farmaco., 56, 821.
Châu Nguyễn Trầm Yên và Bùi Thị Bửu Huê, 2012. Tổng hợp dẫn xuất 4-Oxo-4H-Quinolizine-2-carboxamide. Tạp chí Hóa học, Viện Khoa học và Công nghệ Việt Nam, 50(5A) 105-108.
C. Ochoa and J. J.Rodriguez, 1997. Heterocycl. Chem, 34, 1053-1055.
D. Sharma, B. Narasimhan, P. Kumar and A. Jalbout, 2009. “Synthesis and QSAR evaluation of 2-(substituted phenyl)-1H-benzimidazoles and [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones”. E. J. Medicinal Chemistry, vol. 44, no. 3, pp. 1119-1127.
D. Valdez-Padilla, S. Rodriguez-Morales, A. Hernandez-Cam-pos et al., 2009. “Synthesis and antiprotozoal activity of novel 1-meth-ylbenzimidazole derivatives”. Bioorganic & Medicinal Chemistry, vol. 17, no. 4, pp. 1724-1730.
Donglai Yang, Demosthenes Fokas, Jingzhou Li, Libing Yu and Carmen M. Baldino, 2004. A Versatile Method for the Synthesis of Benzimidazoles from o-Nitroanilines and Aldehydes in One Step via a Reductive Cyclization. Synthesis, No. 1, pp. 0047-0056.
E. Marco, W. Laine, C. Tardy, A. L. Lansiaux, M. Iwao, F. Ishibashi, C. Bailly and F. J. Gago, 2005. Med. Chem., 48, 3796-3807.
G. N. Vazquez, L. Yepez, A. H. Camposetal., 2003. “Synthesis and antiparasitic activity of albendazole and mebendazole analogues”. Bioorganic & Medicinal Chemistry, vol. 11, no. 21, pp. 4615-4622.
G. P. Ellis, 2008. In Chemistry of Heterocyclic Compounds. John Wiley & Sons, Inc.: N.J., U.S.A., Vol. 31, p 921-942.
H. Banie, A. Sinha, R. J. Thomas, J. C. Sircar and M. L. Richards, 2007. “2-phenylimidazopyridines, a new series of golgi compounds with potent antiviral activity”. Journal of Medicinal Chemistry, vol. 50, no. 24, pp. 5984-5993.
H. Goker, C. Kus, D. W. Boykin, S. Yildiz and N. Altanlar, 2002. “Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species”. Bioorganic & Medicinal Chemistry, vol. 10, no. 8, pp. 2589-2596.
J. Chen, Z. Wang and C. M. Li et al., 2010. “Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents”. Journal of Medicinal Chemistry, vol. 53, no. 20, pp. 7414-7427.
J. Mann, A. Baron, Y. Opoku, E. Johansson, G. Parkinson, L. R. Kelland and S. J. Neidle, 2000. Med. Chem., 44, 138-144.
K. J. Spivak and Z. Amit, 1986. “Efects of pimozide on appetitive behavior and locomotor activity: dissimilarity of efects when compared to extinction”. Physiology & Behavior, vol. 36, no. 3, pp. 457-463.L.Garuti, M. Roberti, M. Malagoli, T. Rossi and M. Castelli, 2000. Bioorg. Med. Chem. Lett., 10, 2193.
P. Lindberg, P. Nordberg and T. Alminger et al., 1986. “The mechanism of action of the gastric acid secretion inhibitor omeprazole”. Journal of Medicinal Chemistry, vol. 29, no. 8, pp. 1327-1329.
S. M. Nelson, L. R. Ferguson and W. A. Denny, 2007. Mutat. Res., 623, 24-40.
Vyankat A. Sontakke, Sougata Ghosh, Pravin P. Lawande, Balu A. Chopade and Vaishali S. Shinde, 2013. A Simple, Efficient Synthesis of 2-Aryl Benzimidazoles Using Silica Supported Periodic Acid Catalyst and Evaluation of anticancer Activity. Volume, Article ID 453682, 7 pages.
W. A. Maxwell and G. Brody, 1971. “Antifungal activity of selected benzimidazole compounds”. Applied microbiology, vol. 21, no. 5, pp. 944-945.
Y. F. Li, G. F. Wang and P. L. He et al., 2006. “Synthesis and anti-hepatitis B virus activity of novel benzimidazole derivatives”. Journal of Medicinal Chemistry, vol. 49, no. 15, pp. 4790-4794.
Yi-Sheng Xu, Cheng-Chu Zeng, Zi-Guo Jiao, Li-Ming Hu and Ru-gang Zhong, 2009. Design, Synthesis ang anti-HIV Integrase Evaluation of 4-Oxo-4H-Quinolizine-3-carboxylic Acid Derivatives. Molecules,14, 868-883.