电引发N-自由基激发串联环合制备取代吲哚类化合物任务书

 2022-01-27 03:01

全文总字数:3893字

1. 毕业设计(论文)的内容和要求

1、开题阶段。

搜集大量课题相关的文献,通过文献阅读了解电氧化反应技术以及吲哚类化合物的应用、传统合成方法及优缺点及电氧化偶联的机理理解。

凝练文献要点,形成文献综述。

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2. 实验内容和要求

1、学习并掌握电催化技术的原理和一般操作过程,熟练掌握薄层层析色谱、柱层析分离等有机合成方法;2、筛选得到课题模板反应的最优条件;3、合成10-20个课题所需底物,并完成10-15个相应的底物扩增;4、通过核磁共振、质谱、单晶等分析方法确认所合成化合物的结构正确。

3. 参考文献

1 For selected recent reviews, see (a) D. F. Taber and P. K. Tirunahari, Tetrahedron, 2011, 67, 7195; (b) S. Cacchi and G. Fabrizi, Chem. Rev., 2011, 111, PR215; (c) M. Shiri,Chem. Rev., 2012, 112, 3508; (d) M. Platon, R. Amardeil, L. Djakovitch and J.-C. Hierso, Chem. Soc. Rev., 2012, 41, 3929; (e) M. Inman and C. J. Moody, Chem. Sci., 2013, 4, 29.2 (a) L. S. Hegedus, G. F. Allen, J. J. Bozell and E. L. Waterman, J. Am. Chem. Soc., 1978, 100, 5800; (b) P. J. Harrington and L. S. Hegedus, J. Org. Chem., 1984,49, 2657; (c) P. J. Harrington, L. S. Hegedus and K. F. McDaniel, J. Am. Chem. Soc., 1987, 109, 4335.3 For reviews on Pd(II)-catalyzed CH amination via intramolecular aminopalladation of alkenes for the synthesis of indoles and related heterocycles, see (a) R. I. McDonald, G. Liu and S. S. Stahl, Chem. Rev., 2011, 111, 2981; (b) A. Minatti and K. Muiz, Chem. Soc. Rev., 2007, 36, 1142; (c) T. E. Mller and M. Beller, Chem. Rev., 1998, 98, 675.4 For examples of Pd(II)-catalyzed cyclization of 2-alkenylanilines, see (a) M. E. Krolski, A. F. Renaldo, D. E. Rudisill and J. K. Stille, J. Org. Chem., 1988, 53, 1170; (b) A. Kasahara, T. Izumi, S. Murakami, K. Miyamoto and T. Hino, J. Heterocycl. Chem., 1989, 26, 1405; (c) R. C. Larock, T. R. Hightower, L. A. Hasvold and K. P. Peterson, J. Org. Chem., 1996, 61, 3584; (d) M. Yamaguchi, M. Arisawa and M. Hirama, Chem. Commun., 1998, 1399; (e) D. R. Adams, M. A. J. Duncton, J. R. A. Roffey and J. Spencer, Tetrahedron Lett., 2002, 43, 7581; (f) D. Tsvelikhovsky and S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 14048; (g) S. W. Youn, J. H. Bihn and B. S. Kim, Org. Lett., 2011, 13, 3738. For other related metal-catalyzed or metal-free methods, see (h) T. W. Liwosz and S. R. Chemler, Chem.Eur. J., 2013, 19, 12771; (i) L. Fra, A. Milln, J. A. Souto and K. Muiz, Angew. Chem., Int. Ed., 2014, 53, 7349; (j) Y. H. Jang and S. W. Youn, Org. Lett., 2014, 16, 3720; (k) S. W. Youn, T. Y. Ko, M. J. Jang and S. S. Jang, Adv.Synth. Catal., 2015, 357, 227.5 S. W. Youn, B. S. Kim and A. R. Jagdale, J. Am. Chem. Soc., 2012, 134, 11308.6 For selected recent examples, see (a) E. del Ro, M. I. Menndez, R. Lpez and T. L. Sordo, J. Am. Chem. Soc., 2001, 123, 5064; (b) I. Manet, S. Monti, G. Grabner, S. Protti, D. Dondi, V. Dichiarante, M. Fagnoni and A. Albini, Chem. Eur. J., 2008, 14, 1029; (c) K. Sun, S. Liu, P. M. Bec and T. G. Driver, Angew. Chem., Int. Ed., 2011, 50, 1702; (d) F. V. Singh, J. Rehbein and T. Wirth, ChemistryOpen, 2012, 1, 245 andref. 4ik.7 (a) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689; (b) R. C. Larock, E. K. Yum and M. D. Refvik, J. Org. Chem., 1998, 63, 7652; (c) D. R. Stuart, M. BertrandLaperle, K. M. N. Burgess and K. Fagnou, J. Am. Chem. Soc.,2008, 130, 16474; (d) D. R. Stuart, P. Alsabeh, M. Kuhn and K. Fagnou, J. Am. Chem. Soc., 2010, 132, 18326; (e) L. Ackermann and A. V. Lygin, Org. Lett., 2012, 14, 764.8 For examples of CuX2-promoted halogenation at the C3 position of the indole nucleus, see (a) E. Balogh-Hergovich and G. Speier, J. Chem. Soc., Perkin Trans. 1, 1986, 2305; (b) S. Tang, J.-H. Li, Y.-X. Xie and N.-X. Wang, Synthesis,2007, 1535; (c) G. Broggini, V. Barbera, E. M. Beccalli, E. Borsini, S. Galli, G. Lanza and G. Zecchi, Adv. Synth. Catal., 2012, 354, 159.

4. 毕业设计(论文)计划

2020.12.30-2021.1.31:毕业论文开题准备,撰写开题报告;2021.3.1-4.15:完成课题实验并整理数据;2021.4.16-2021.5.20:完成毕业论文撰写和论文答辩;2021.5.20-2021.5.25:毕业论文修订,整理。

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