Application of Ugi/De-Boc/Cyclization Strategy in the Synthesis of Nitrogen-Containing Heterocycles
- Corresponding author: Guo Changbin, guocb@cnu.edu.cn
Citation:
Zhang Zhaorui, Zheng Xiaolin, Guo Changbin. Application of Ugi/De-Boc/Cyclization Strategy in the Synthesis of Nitrogen-Containing Heterocycles[J]. Chinese Journal of Organic Chemistry,
;2016, 36(6): 1241-1265.
doi:
10.6023/cjoc201511004
Zhang, X.-N.; Li, Y.-X.; Zhang, Z.-H. Tetrahedron 2010, 67, 7426.
Schwerkoske, J.; Masquelin, T.; Perun, T.; Hulme, C. Tetrahedron Lett. 2005, 46, 8355.
Boomhoff, M.; Yadav, A. K.; Appun, J.; Schneider, C. Org. Lett. 2014, 16, 6236.
Kalinski, C.; Umkehrer, M.; Weber, L.; Kolb, J.; Burdack, C.; Ross, G. Mol. Diversity 2010, 14, 513.
Sun, J.; Shen, G. L.; Xie, Y. J.; Yan, C. G. Chin. J. Chem. 2014, 32, 1143.
Guo, R.-Y.; An, Z.-M.; Mo, L.-P.; Wang, R.-Z.; Liu, H.-X.; Wang, S.-X.; Zhang, Z.-H. ACS Comb. Sci. 2013, 15, 557.
Ugi, I.; Meyr, R.; Fetzer, U. Angew. Chem. 1959, 71, 386.
Ugi, I. Steinbrückner, C. Angew. Chem. 1960, 72, 267.
Kalinski, C.; Umkehrer, M.; Gonnard, S.; Jager, N.; Ross, G.; Hiller, W. Tetrahedron Lett. 2006, 47, 2041.
Gordillo-Cruz, R. E.; Renteria-Gomez, A.; Islas-Jacome, A.; Cortes-Garcia, C. J.; Diaz-Cervantes, E.; Robles, J.; Gamez-Mon- tano, R. Org. Biomol. Chem. 2013, 11, 6470.
Zeng, X.-H.; Wang, H.-M.; Ding, M.-W. Org. Lett. 2015, 17, 2234.
Barlow, T. M. A.; Jida, M.; Tourwe, D.; Ballet, S. Org. Biomol. Chem. 2014, 12, 6986.
Peshkov, A. A.; Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Tetrahedron 2015, 71, 3863.
Saha, D.; Wadhwa, P.; Sharma, A. RSC Adv. 2015, 5, 33067.
Yerande, S. G.; Newase, K. M.; Singh, B.; Boltjes, A.; Domling, A. Tetrahedron Lett. 2014, 55, 3263.
Hulme, C.; Peng, J.; Tang, S. Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021.
Parks, D. J.; LaFrance, L. V.; Calvo, R. R.; Milkiewicz, K. L.; Gupta, V.; Lattanze, J.; Ramachandren, K.; Carver, T. E.; Petrella, E. C.; Cummings, M. D.; Maguire, D.; Grasberger, B. L.; Lu, T. Bioorg. Med. Chem. Lett. 2005, 15, 765.
Zhang, W.; Tempest, P. Tetrahedron Lett. 2004, 45, 6757.
Dai, W.-M.; Shi, J, Y. Comb. Chem. High Throughput Screening 2007, 10, 837.
Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
Hulme, C.; Ma, L.; Cherrier, M. P.; Romano, J. J.; Morton, G.; Duquenne, C.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1883.
Hulme, C.; Ma, L.; Romano, J. J.; Morton, G.; Tang, S. Y.; Cherrier, M. P.; Choi, S.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1889.
Hulme, C.; Ma, L.; Romano, J.; Morrissette, M. Tetrahedron Lett. 1999, 40, 7925.
Zhan, P.; Chen, X. W.; Li, D. Y.; Fang, Z. J.; De Clercq, E.; Liu, X. Y. Med. Chem. Commun. 2013, 33, S1.
Huang, S.-T.; Hsei, I.-J.; Chen, C. Bioorg. Med. Chem. 2006, 14, 6106.
Goodwin, K. D.; Lewis, M. A.; Tanious, F. A.; Tidwell, R. R.; David, W. W.; Georgiadis, M. M.; Long, E. C. J. Am. Chem. Soc. 2006, 128, 7846.
Lin, Y.-Z.; Wang, T.-H.; Lin, Y.-S.; Kuan, W.-C.; Lee, W.-C. J. Appl. Polym. Sci. 2014, 131, 40725.
Xiong, J.-F.; Luo, S.-H.; Huo, J.-P.; Liu, J.-Y.; Chen, S.-X.; Wang, Z.-Y. J. Org. Chem. 2014, 79, 8366.
Tempest, P.; Ma, V.; Thomas, S.; Hua, Z.; Kelly, M. G.; Hulme, C. Tetrahedron Lett. 2001, 42, 4959.
Carbajales, C.; Prado, M. A.; Gutierrez-de-Teran, H.; Cores, A.; Azuaje, J.; Novio, S.; Nunez, M. J.; Fernandez-Garcia, B.; Sotelo, E.; Garcia-Mera, X.; Sanchez-Lazo, P.; Freire-Garabal, M.; Coelho, A. ChemBioChem 2014, 15, 1471.
Tempest, P.; Ma, V.; Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963.
Xu, Z. G.; Shaw, A. Y.; Dietrich, J.; Cappelli, A. P.; Nichol, G.; Hulme, C. Mol. Diversity 2012, 16, 73.
Shaw, A. Y.; Medda, F.; Hulme, C. Tetrahedron Lett. 2012, 53, 1313.
Xu, Z. G; Ayaz, M.; Cappelli, A. A.; Hulme, C. ACS Comb. Sci. 2012, 14, 460.
Xu, Z. G.; Shaw, A. Y.; Nichol, G. S.; Cappelli, A. P.; Hulme, C. Mol. Diversity 2012, 16, 607.
Xu, Z, G.; Martinez-Ariza, G.; Cappelli, A. P.; Roberts, S. A. J. Org. Chem. 2015, 80, 9007.
Song, G.-T.; Li, S.-Q.; Yang, Z.-W.; Yuan, J.-H.; Wang, M.-S.; Zhu, J.; Chen Z.-Z.; Xu, Z.-G. Tetrahedron Lett. 2015, 56, 4616.
Ozkay, Y.; Tunal, Y.; Karaca, H.; Ilhan, I. Eur. J. Med. Chem. 2010, 45, 3293.
Chen, Z.-Z.; Zhang, J.; Tang, D.-Y.; Xu, Z.-G. Tetrahedron Lett. 2014, 55, 2742.
Hulme, C.; Chappeta, S.; Griffith, C.; Lee, Y.-S.; Dietrich, J. Tetrahedron Lett. 2009, 50, 1939.
Nixey, T.; Kelly, M.; Semin, D.; Hulme, C. Tetrahedron Lett. 2002, 43, 3681.
Medda, F.; Martinez-Ariza, G.; Hulme, C. Tetrahedron Lett. 2015, 56, 5295.
Davenport, A. J.; Stimson, C. C.; Corsi, M.; Vaidya, D.; Glenn, E.; Jones, T. D.; Bailey, S.; Gemkow, M. J.; Fritz, U.; Hallett, D. J. Bioorg. Med. Chem. Lett. 2010, 20, 5165.
Gunawan, S.; Hulme, C. Org. Biol. Chem. 2013, 11, 6036.
Gunawan, S.; Petit, J.; Hulme, C. ACS Comb. Sci. 2012, 14, 160.
Gunawan, S.; Nichol, G.; Hulme, C. Tetrahedron Lett. 2012, 53, 1664.
Cao, S.; Zhong, S. S.; Hu, C. F.; Wan, J.-P.; Wen, C. P. Chin. J. Chem. 2015, 33, 568.
Xu, Z. G.; Moliner, F. D.; Cappelli, A. P.; Hulme, C. Angew. Chem., Int. Ed. 2012, 51, 8037.
Achour, R.; Essassi, E. M.; Zniber, R. Tetrahedron Lett. 1988, 29, 195.
Hulme, C.; John, P.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N. V. Tetrahedron Lett. 1998, 39, 8047.
Xu, Z. G.; Moliner, F. D.; Cappelli, A. P.; Ayaz, M.; Hulme, C. Synlett 2014, 25, 225.
Houston, D. R.; Synstad, B.; Eijsink, V. G. H.; Stark, M. J. R.; Eggleston, I. M.; van Aalten, M. F. J. Med. Chem. 2004, 47, 5713.
Van de Merwe, E.; Huang, D.; Peterson, D.; Kilian, G.; Milne, P. J.; Van de Vanter, M.; Frost, C. Peptides. 2008, 29, 1305.
Rhoden, C. R. B.; Rivera, D. G.; Kreye, O.; Bauer, A. K.; Westermann, B.; Wessjohann, L. A. J. Comb. Chem. 2009, 11, 1078.
Hulme, C.; Cherrier, M.-P. Tetrahedron Lett. 1999, 40, 5295.
Ji, F.; Yi, W. B.; Cai, C. J. Heterocycl. Chem. 2014, 51, 1287.
Hulme, C.; John, P.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227.
Raillard, S. P.; Ji, G. J.; Mann, A. D.; Baer, T. A. Org. Process Res. Dev. 1999, 3, 177.
Golebiowski, A.; Jozwik, J.; Klopfenstein, S. R.; Colson, A. O.; Grieb, A. L.; Russell, A. F.; Rastogi, V. L.; Diven, C. F.; Portlock, D. E.; Chen, J. J. J. Comb. Chem. 2002, 4, 584.
Cano-Herrera, M.-A.; Miranda, L. D. Chem. Commun. 2011, 47, 10770.
Nixey, T.; Tempest, P.; Hulme, C. Tetrahedron Lett. 2002, 43, 1637.
Dalvi, P. B.; Lin, S.-F.; Paike, V.; Sun, C.-M. ACS Comb. Sci. 2015, 17, 421.
Ayaz, M.; Guillermo, M. A.; Hulme, C. Synlett 2014, 25, 1680.
Azuaje, J.; Maatougui, A. E.; Garcia-Mera, X.; Sotelo, E. ACS Comb. Sci. 2014, 16, 403.
Ayaz, M.; Xu, Z. G.; Hulme, C. Tetrahedron Lett. 2014, 55, 3406.
Gunawan, S.; Nichol, G.; Hulme, C. Tetrahedron Lett. 2012, 53, 1664.
Zhang, Z.-H.; Zhang, X.-N.; Mo, L.-P.; Li, Y.-X.; Ma, F.-P. Green Chem. 2012, 14, 1502.
Zhang, Z.-H.; Lu, H.-Y.; Yang, S.-H.; Gao, J.-W. J. Comb. Chem. 2010, 12, 643.
Noolvi, M. N.; Patel, H. M.; Bhardwaj, V.; Chauhan, A. Eur. J. Med. Chem. 2011, 46, 2327.
Youssef, K.; Nadine, A.; Aurelien, D.; Sebastien, H.; Michele, L.; Pierre, V.; Armand, G.; Patrice, V. Eur. J. Med. Chem. 2010, 45, 616.
Tiwari R.; Chhabra, G. Asian J. Chem. 2010, 22, 5981.
Dietrich, J.; Kaiser, C.; Meurice, N.; Hulme, C. Tetrahedron Lett. 2010, 51, 3951.
Azuaje, J.; Maatougui, A. E.; Perez-Rubio, J. M.; Coelho, A.; Fernandez, F.; Sotelo, E. J. Org. Chem. 2013, 78, 4402.
Qneibi, M. S.; Micale, N.; Grasso, S.; Niu, L. Biophys. J. 2013, 104, 1405.
Qneibi, M. S.; Micale, N.; Grasso, S.; Niu, L. Biochemistry 2012, 51, 1787.
Anzini, M.; Valenti, S.; Braile, C.; Cappelli, A.; Vomero, S.; Alcaro, S.; Ortuso, F.; Marinelli, L.; Limongelli, V.; Novellino, E.; Betti, L.; Giannaccini, G.; Lucacchini, A.; Daniele, S.; Martini, C.; Ghelardini, C.; Mannelli, L. D.; Giorgi, G.; Mascia, M. P.; Biggio, G. J. Med. Chem. 2011, 54, 5694.
Liu, P.; Lanza, T. J.; Chioda, M.; Jones, C.; Chobanian, H. R.; Guo, Y.; Chang, L.; Kelly, T. M.; Kan, Y.; Palyha, O.; Guan, X.-M.; Marsh, D. J.; Metzger, J. M.; Ramsay, K.; Wang, S.-P.; Strack, A. M.; Miller, R.; Pang, J.; Lyons, K.; Dragovic, J.; Ning, J. G.; Schafer, W. A.; Welch, C. J.; Gong, X.; Gao, Y.-D.; Hornak, V.; G. Ball, R.; Tsou, N.; Reitman, M. L.; Wyvratt, M. J.; Nargund, R. P.; Lin, L. S. ACS Med. Chem. Lett. 2011, 2, 933.
Huang, Y.; Wolf, S.; Bista, M.; Meireles, L.; Camacho, C.; Holak, T. A.; Domling, A. Chem. Biol. Drug Des. 2010, 76, 116.
Huang, Y.; Domling, A. Chem. Biol. Drug Des. 2010, 76, 130.
Huang, Y.; Khoury, K.; Chanas, T.; Domling, A. Org. Lett. 2012, 14, 5916.
Gordon, C. P.; Young, K. A.; Hizartzidis, L.; Deane, F. M.; McCluskey, A. Org. Biomol. Chem. 2011, 9, 1419.
Tempest, P.; Pettus, L.; Gore, V.; Hulme, C. Tetrahedron Lett. 2003, 44, 1947.
Azuaje, J.; Perez-Rubio, J. M.; Yaziji, V.; Maatougui, A. E.; Gonzalez-Gomez, J. C.; Sanchez-Pedregal, V. M.; Navarro-Vazquez, A.; Masaguer, C. F.; Teijeira, M.; Sotelo, E. J. Org. Chem. 2015, 80, 1533.
Huang, Y.; Khoury, K.; Chanas, T.; Domling, A. Org. Lett. 2012, 14, 5916.
Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509.
Zhou, H.; Zhang, W.; Yan, B. J. Comb. Chem. 2010, 12, 206.
Gunawan, S.; Nichol, G. S.; Chappeta, S.; Dietrich, J.; Hulme, C. Tetrahedron Lett. 2010, 51, 4689.
Gunawan, S.; Ayaz, M.; Moliner, F. D.; Frett, B.; Kaiser, C.; Patrick, N.; Xu, Z.; Hulme, C. Tetrahedron 2012, 68, 5606.
Xu, Z. G.; Dietrich, J.; Shaw, A. Y.; Hulme. C. Tetrahedron Lett. 2010, 51, 4566.
Brown, A. L.; Churches, Q. I.; Hutton, C. A. J. Org. Chem. 2015, 80, 9831.
Boger, D. L.; Saionz, K. W. Bioorg. Med. Chem. 1999, 7, 315.
Katayama, K.; Nakagawa, K.; Takeda, H.; Matsuda, A.; Ichikawa, S. Org. Lett. 2014, 16, 428.
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033