Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

doi:10.6023/cjoc201601013

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 875-888.DOI: 10.6023/cjoc201601013 Previous Articles Next Articles

REVIEW

基于C—H键官能团化/环化串联策略构建吲哚酮分子骨架的研究进展

阿布力米提·阿布都卡德尔^a, 张永红^a, 张增鹏^a, 刘晨江^a,b

a. 新疆大学化学化工学院乌鲁木齐 830046;
b. 新疆大学理化测试中心乌鲁木齐 830046

收稿日期:2016-01-12 修回日期:2016-03-28 发布日期:2016-04-05
通讯作者: 刘晨江 E-mail:pxylcj@126.com
基金资助:
国家自然科学基金(Nos.21572195,21562039,21502162)资助项目.

Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

Abdukader Ablimit^a, Zhang Yonghong^a, Zhang Zengpeng^a, Liu Chenjiang ^a,b

a. School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046;
b. Physics and Chemistry Detecting Center, Xinjiang University, Urumqi 830046

Received:2016-01-12 Revised:2016-03-28 Published:2016-04-05
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572195, 21562039, 21502162).

Due to the diverse biological activities of indolinones, especially 3,3-disubstituted indolinones, their researches of synthesis have been attracting considerable interest in the areas of organic chemistry. Recently, the radical addition and cyclization reaction of N-arylacrylamides with different radical precursors for the efficient construction of indolinones motifs have attracted much attention. This review summarizes the recent advances of the access to 3,3-disubstituted indolinones based on C—H bond functionalization/cyclization cascade strategy. These reaction mechanisms have also been introduced.

Key words: C—H functionalization, oxindoles, cascade reaction

Cite this article

Abdukader Ablimit, Zhang Yonghong, Zhang Zengpeng, Liu Chenjiang. Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy[J]. Chin. J. Org. Chem., 2016, 36(5): 875-888.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed.2007, 46, 8748.
(b) Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 4527.
(c) Leptosin, D; Takahashi, C.; Numata, A.; Ito, Y.; Matsumura, E.; Araki, H.; Iwaki, H.; Kushida, K. J. Chem. Soc., Perkin Trans.1 1994, 1859.
(d) Ma, J.; Hecht, S. M. Chem. Commun. 2004, 1190.
[2] Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth.Catal. 2010, 352, 1381.
[3] (a) Shen, K.; Liu, X.-H.; Lin, L.-L.; Feng, X.-M. Chem. Sci. 2012, 3, 327.
(b) Trost, B. M.; Xie, J.; Sieber, J. D. J. Am. Chem. Soc. 2011, 133, 20611.
[4] Abelman, M.; Oh, T.; Overman, L. J. Org. Chem. 1987, 52, 4130.
[5] Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem. Eur. J. 2007, 13, 961.
[6] Klein, J.; Taylor, R. Eur. J. Org. Chem.2011, 6821.
[7] Jia, Y.-X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636.
[8] (a) Jaegli, S.; Dufour, J.; Wei, H.-L.; Piou, T.; Duan, X.-H.; Vors, J.-P.; Neuville, L.; Zhu, J. Org. Lett. 2010, 12, 4498.
(b) Piou, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed.2012, 51, 11561.
(c) Trost, B. M.; Brennan, M., K. Synthesis 2009, 3003.
[9] Wu, T.; Mu, X.; Liu, G.-S. Angew. Chem., Int. Ed.2011, 50, 12578.
[10] Mu, X.; Wu, T.; Wang, H.-Y.; Guo, Y.-L.; Liu, G.-S. J. Am. Chem. Soc. 2012, 134, 878.
[11] Wei, W.-T.; Zhou, M.-B.; Fan, J.-H.; Liu, W.; Song, R.-J.; Liu, Y.; Hu, M.; Xie, P.; Li, J.-H. Angew. Chem., Int. Ed. 2013, 52, 3638.
[12] Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2013, 49, 10370.
[13] Li, Z.; Zhang, Y.; Zhang, L.; Liu, Z.-Q. Org. Lett.2014, 16, 382.
[14] Dai,Q.; Yu,J.; Jiang, Y.; Guo, S.; Yang, H.; Cheng, J. Chem. Commun.2014, 50, 3865.
[15] Meng, Y.; Guo, L.-N.; Wang, H.; Duan, X.-H. Chem. Commun. 2013, 49, 7540.
[16] Lu, M.-Z.; Loh, T.-P. Org. Lett. 2014, 16, 4698.
[17] Xie, J.; Xu, P.; Li, H.-M.; Xue, Q.-C.; Jin, H.-M.; Cheng, Y.-X.; Zhu, C.-J. Chem. Commun.2013, 49, 5672.
[18] (a) Pan, C.-D.; Zhang, H.-L.; Zhu, C.-J. Org. Biomol. Chem. 2015, 13, 361.
(b) Li, J.; Wang, Z.-G.; Wu, N.-J.; Gao, G.; You, J.-S. Chem. Commun. 2014, 50, 15049.
[19] Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed.2005, 44, 214.
[20] Xu, P.; Xie, J.; Xue, Q.-C.; Pan, C.-D.; Cheng, Y.-X.; Zhu,C.-J. Chem. Eur. J. 2013, 19, 14039.
[21] Yang, F.; Klumphu, P.; Liang, Y.-M.; Lipshutz, B. H. Chem.Commun. 2014, 50, 936.
[22] (a) Fu, W.-J.; Xu, F.-J.; Fu, Y.-Q.; Xu, C.; Li, S.-H.; Zou, D.-P. Eur. J. Org. Chem. 2014, 709.
(b) Li, L.; Deng, M.; Zheng, S.-C.; Xiong, Y.-P.; Tan, B.; Liu, X.-Y. Org. Lett. 2014, 16, 504.
[23] Tang, X.-J.; Thomoson, C. S.; Dolbier, Jr. W. R. Org.Lett. 2014, 16, 4594.
[24] Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128.
[25] Wang, J.-Y.; Su, Y.-M.; Yin, F.; Bao, Y.; Zhang, X.; Xu, Y.-M.; Wang, X.-S. Chem. Commun.2014, 50, 4108.
[26] (a) Li, Z.; Cao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 6505.
(b) Kim, H. J.; Kim, J.; Cho, S. H.; Chang,S. J. Am. Chem. Soc. 2011, 133, 16382.
(c) Xue, Q.-X.; Xie, J.; Li, H.-M.; Cheng, Y.-X.; Zhu, C.-J. Chem.Commun. 2013, 49, 3700.
[27] Zhou, S.-L.; Guo, L.-N.; Wang, H.; Duan, X.-H. Chem. Eur. J.2013, 19, 12970.
[28] Zhou, M.-B.; Wang, C.-Y.; Song, R.-J.; Liu, Y.; Wei, W.-T.; Li, J.-H. Chem. Commun.2013, 49, 10817.
[29] (a) Galli, C. Chem.Rev. 1988, 88, 765.
(b) Heinrich, M. R. Chem. Eur. J.2009, 15, 820.
[30] Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[31] Fu, W.-J.; Xu, F.-J.; Fu, Y.-Q.; Zhu, M.; Yu, J.-Q.; Xu, C.; Zou, D.-P. J. Org. Chem. 2013, 78, 12202.
[32] Zhou, M.-B.; Song R.-J.; Ouyang, X.-H.; Liu, Y.; Wei, W.-T.; Deng, G.-B.; Li, J.-H. Chem. Sci. 2013, 4, 2690.
[33] Wang, H.; Guo, L.-N.; Duan, X.-H. Adv. Synth. Catal. 2013, 355, 2222.
[34] (a) Pinhoe Melo, T. M. V. D. In Organic Azides: Syntheses and Applications, Eds.: Bräse, S.; Banert, K., Wiley-VCH, Weinheim, 2010, Vol. 53.
(b) Bräse, S.; Banert, K. In Organic Azides, Wiley-VCH, Weinheim, 2010.
(c) Jung, N.; Bräse, S. Angew.Chem. Int. Ed. 2012, 51, 12169.
[35] Jimeno, C.; Renaud, P. Radical Chemistry with Azides, in Organic Azides: Syntheses and Applications, Eds.: Braase, S.; Banert, K., Wiley, Chichester, 2010.
[36] Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985.
[37] (a) Yuan, Y.-Z.; Shen, T.; Wang, K.; Jiao, N. Chem. Asian J. 2013, 8, 2932.
(b) Wei, X.-H.; Li, Y.-M.; Zhou, A.-X.; Yang, T.-T.; Yang, S.-D. Org. Lett. 2013, 15, 4158.
[38] Qiu, J.; Zhang, R.-H. Org. Biomol. Chem. 2014, 12, 4329.
[39] Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
[40] Li, Y.-M.; Wei, X.-H.; Li, X.-A.; Yang, S.-D. Chem. Commun. 2013, 49, 11701.
[41] Shen, T.; Yuan, Y.-Z.; Jiao, N. Chem. Commun. 2014, 50, 554.
[42] (a) Van der Jeught, S.; Stevens, C. V. Chem. Rev. 2009, 109, 2672.
(b) George, A.; Veis, A. Chem. Rev. 2008, 108, 4670.
[43] Allen, D. W. Organophosphorus Chem. 2010, 39, 1.
[44] (a) Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.
(b) Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991.
[45] Fontecave, M.; Ollagnier-de-Choudens, S.; Mulliez, E. Chem. Rev. 2003, 103, 2149.
[46] Bertrand, M. P.; Ferreri, C. In Radicals in Organic Synthesis, Eds.: Renaud, P.; Sibi, M., Wiley-VCH, Weinheim, 2001, Vol. 2, pp 485~504.
[47] Li, X.; Xu, X.-S.; Hu, P.-Z.; Xiao, X.-Q.; Zhou, C. J. Org. Chem. 2013, 78, 7343.
[48] Shen, T.; Yuan, Y.-Z.; Song, S.; Jiao, N. Chem. Commun. 2014, 50, 4115.
[49] Li, C-C.; Yang, S.-D. Org. Lett. 2015, 17, 2142.
[50] (a) Purser, S.; Moore, P. R.; Swallow, S.; Governeur, V. Chem. Soc. Rev. 2008, 37, 320.
(b) Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950.
(c)Tomashenko, O. A; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
[51] Kong, W.-Q.; Casimiro, M; Merino, E; Nevado, C. J. Am. Chem. Soc. 2013, 135,14480.
[52] Kong, W.-Q.; Casimiro, M.; Fuentes, N.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 13086.

基于C—H键官能团化/环化串联策略构建吲哚酮分子骨架的研究进展

Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[2]	Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002.
[3]	Yun Shi, Ting Xiao, Dong Xia, Wenchao Yang. SCF₃ Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2715-2727.
[4]	Xiaozheng Zhao, Qinqin Ling, Guiyan Cao, Xing Huo, Xiaolong Zhao, Yingpeng Su. Research Progress in the Cyclization Reactions with Propargyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2605-2639.
[5]	Xuyu Zhou, Aijun Zhang, Qingqing Zhang, Qing'an Liu, Jun Xuan. Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2488-2495.
[6]	Xin Sun, Chaofan Qu, Chaorui Ma, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang. Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1396-1406.
[7]	Liwei Xiao, Guangxian Liu, Ping Ren, Tongtong Wu, Yuwei Lu, Jie Kong. Elemental Sulfur: An Excellent Sulfur-Source for Synthesis of Sulfur-Containing Heterocyclics [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1002-1012.
[8]	Kemiao Hong, Jingjing Huang, Minghan Yao, Xinfang Xu. Recent Advances in Nitrene/Alkyne Metathesis Cascade Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 344-352.
[9]	Fangjie Li, Bin Lu, Yang Liu, Xiaoming Wang. Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3390-3397.
[10]	Qisheng Gao, Qi Jing, Yang Chen, Jing Sun, Mingdong Zhou. Decarboxylative Amidation of Acrylamides with Oxamic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 257-265.
[11]	Shuyan Yu, Lihong Gao, Yizhe Yan, Zhigang Yin, Yongjia Shang. Application of Cascade Reactions in the Synthesis of Sprio-hetero- cycles Initiated by Intramolecular Cyclization of Alkynols [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 582-593.
[12]	Wenbo Wang, Huabin Han, Lele Wang, Qilin Wang, Zhanwei Bu. Access to Tetrasubstituted Tri(indolyl)methanes through Copper-Catalyzed Addition/Substitution Sequence [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 757-765.
[13]	Ning Zou, Xiaoting Qin, Zhixin Wang, Weimin Shi, Dongliang Mo. Advances on the Synthesis and Application of α,β-Unsaturated Nitrones [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4535-4553.
[14]	Xuehua Liu, Chuanchuan Wang, Xinlu Wang, Zhiwei Ma, Lei Meng, Degang Ding, Juntao Liu, Yajing Chen. Synthesis of Spirobarbiturate Piperidin-2-one Derivatives via Cascade Aza-Michael/Michael Cyclization Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4450-4458.
[15]	Yitong Liu, Xiyuan Zhang, Zhiwei Miao. Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3965-3982.