Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition Reactions: Synthesis of 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones
作者： Zhiguo Zhang , Xiaolong Gao , Yameng Wan , Yuanyuan Huang , Guoqing Huang
关键词:
摘要: An efficient tandem intermolecular one-pot aldol condensation/aza-addition reaction of 2-methyl-3-carbamoylpyrroles and aldehydes was developed for the synthesis 2,3,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones. The proceeded using only 3.0 equiv ammonium acetate promoter in green solvent poly(ethylene glycol)-400 at 100 °C to afford a series pyrrolo[3,2-c]pyridinone derivatives good excellent yields.
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Zhiguo Zhang, Lianqiang Zhang, Xinyu Duan, Xiangqian Yan, Yan Yan, Qingfeng Liu, Tongxin Liu, Guisheng Zhang, Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones Tetrahedron. ,vol. 71, pp. 7745- 7751 ,(2015) , 10.1016/J.TET.2015.07.039
Mohammed I. El-Gamal, Mohammed S. Abdel-Maksoud, Mahmoud M. Gamal El-Din, Kyung Ho Yoo, Daejin Baek, Chang-Hyun Oh, Cell‐Based Biological Evaluation of a New Bisamide FMS Kinase Inhibitor Possessing Pyrrolo[3,2‐c]pyridine Scaffold Archiv Der Pharmazie. ,vol. 347, pp. 635- 641 ,(2014) , 10.1002/ARDP.201400051
Xue-Qing Mou, Zheng-Liang Xu, Shao-Hua Wang, Dao-Yong Zhu, Jie Wang, Wen Bao, Shi-Jiang Zhou, Chao Yang, Di Zhang, An Au(I)-catalyzed rearrangement/cyclization cascade toward the synthesis of 2-substituted-1,4,5,6-tetrahydrocyclopenta[b]pyrrole Chemical Communications. ,vol. 51, pp. 12064- 12067 ,(2015) , 10.1039/C5CC03979G
Luyong Wu, Shu Guo, Xianghui Wang, Zhifang Guo, Guogui Yao, Qiang Lin, Mingshu Wu, Tandem synthesis of 2-aryl-1,2,3-triazoles from α-arylhydrazonoketones with NH4OAc via copper-catalyzed aerobic oxidation Tetrahedron Letters. ,vol. 56, pp. 2145- 2148 ,(2015) , 10.1016/J.TETLET.2015.03.019
Tjeerd Barf, Allard Kaptein, Sander de Wilde, Ruud van der Heijden, Richard van Someren, Dennis Demont, Carsten Schultz-Fademrecht, Judith Versteegh, Mario van Zeeland, Nicole Seegers, Bert Kazemier, Bas van de Kar, Maaike van Hoek, Jeroen de Roos, Henri Klop, Ruben Smeets, Claudia Hofstra, Jorrit Hornberg, Arthur Oubrie, Structure-based lead identification of ATP-competitive MK2 inhibitors. Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 3818- 3822 ,(2011) , 10.1016/J.BMCL.2011.04.018
Gerard M. P. Giblin, Andrew Billinton, Michael Briggs, Andrew J. Brown, Iain P. Chessell, Nick M. Clayton, Andrew J. Eatherton, Paul Goldsmith, Carl Haslam, Matthew R. Johnson, William L. Mitchell, Alan Naylor, Alcide Perboni, Brian P. Slingsby, Alex W. Wilson, Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB2 Agonist for the Treatment of Chronic Pain Journal of Medicinal Chemistry. ,vol. 52, pp. 5785- 5788 ,(2009) , 10.1021/JM9009857
J.P. Celerier, M. Haddad, D. Jacoby, G. Lhommet, Heterocyclization of primary amines with highly activated cyclopropanes: a new route to isoretronecanol Tetrahedron Letters. ,vol. 28, pp. 6597- 6600 ,(1987) , 10.1016/S0040-4039(00)96923-5
Allard Kaptein, Arthur Oubrie, Edwin de Zwart, Niels Hoogenboom, Joeri de Wit, Bas van de Kar, Maaike van Hoek, Gerard Vogel, Vera de Kimpe, Carsten Schultz-Fademrecht, Judith Borsboom, Mario van Zeeland, Judith Versteegh, Bert Kazemier, Jeroen de Roos, Frank Wijnands, John Dulos, Martin Jaeger, Paula Leandro-Garcia, Tjeerd Barf, Discovery of selective and orally available spiro-3-piperidyl ATP-competitive MK2 inhibitors. Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 3823- 3827 ,(2011) , 10.1016/J.BMCL.2011.04.016
Haiyang Fei, Jintao Yu, Yan Jiang, Huan Guo, Jiang Cheng, The ammonium-promoted formylation of indoles by DMSO and H2O Organic and Biomolecular Chemistry. ,vol. 11, pp. 7092- 7095 ,(2013) , 10.1039/C3OB41510D
Zhiguo Zhang, Dan Wang, Bing Wang, Qingfeng Liu, Tongxin Liu, Wei Zhang, Beibei Yuan, Zhijia Zhao, Dandan Han, Guisheng Zhang, None, SnCl4 mediated synthesis of γ-amino ketones derivatives via the ring-opening reaction of 4,5-dihydropyrroles Tetrahedron. ,vol. 69, pp. 9063- 9067 ,(2013) , 10.1016/J.TET.2013.08.027