Citation: Ding Bangdong, Jiang Yechao, Zhang Yu, Ye Rong, Sun Jin, Yan Chaoguo. Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1, 3-Indanedione and 2-Arylidene-1, 3-indanediones[J]. Chinese Journal of Organic Chemistry, ;2020, 40(4): 1003-1016. doi: 10.6023/cjoc201910016 shu

Synthesis of Indanone-Containing Heterocycles via Cycloaddition Reaction of Quinolinium Ylides with 1, 3-Indanedione and 2-Arylidene-1, 3-indanediones

Ding Bangdong ^a ,
Jiang Yechao ^a ,
Zhang Yu ^b ,
Ye Rong ^b ,
Sun Jin ^b ,
Yan Chaoguo ^b,,

a.
College of Chemical Engineering, Yangzhou Polytechnic Institute, Yangzhou, Jiangsu 225127
b.
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Corresponding author: Yan Chaoguo, cgyan@yzu.edu.cn
Received Date: 12 October 2019
Revised Date: 13 November 2019
Available Online: 2 December 2019
Fund Project: the National Natural Science Foundation of China 21572196Project supported by the National Natural Science Foundation of China (No. 21572196) and the Priority Academic Program Development of Jiangsu Higher Education Institutions

Figures(7)

The triethylamine promoted cycloaddition reaction of N-phenacylquinolinium bromide with 1, 3-indanedione gave functionalized dihydropyrrolo[1, 2-a]quinolines as main products and 2-(1-(2-oxo-2-phenylethyl)-quinolin-4-ylidene)-indene-1, 3-diones as minor products. The similar reaction with N-benzylquinolinium bromide gave 2-(1-(2-oxo-2-phenylethyl)-quino-lin-4-ylidene)-indene-1, 3-diones as major products. On the other hand, triethylamine promoted three-component reaction of N-phenacyl, N-ethoxycarbonylmethyl and N-(4-nitrobenzyl)quinolinium salts, aromatic aldehydes and 1, 3-indanedione in ethanol at room temperature afforded functionalized spiro[indene-2, 3'-pyrrolo[1, 2-a]quinolone]s in good yields and with high diastereoselectivity.
- heteroaromatic N-ylide,
- quinolinium bromide,
- 1, 3-indanedione,
- spiro compound,
- [3+2] cycloaddition,
- diastereo-selectivity
1. [1]
  (a) Addla, D.; Bhima; Sridhar, B.; Devi, A.; Kantevari, S. Bioorg. Med. Chem. Lett. 2012, 22, 7475.
  (b) Chakrabarty, S.; Croft, M. S.; Marko, M. G.; Moyna, G. Bioorg. Med. Chem. 2013, 21, 1143/
  (c) Muscia, G. C.; Buldain, G. Y.; Asis, S. E. Eur. J. Med. Chem. 2014, 73, 243.
2. [2]
  (a) Huang, H.-H.; Prabhakar, Ch.; Tang, K.-C.; Chou, P. T.; Huang, G. J.; Yang, J. S. J. Am. Chem. Soc. 2011, 133, 8028.
  (b) Gomez-Esteban, S.; Benito-Hernandez, A.; Termine, R.; Hennrich, G.; Navarrete, J. T. L.; Ruiz Delgado, M. C.; Golemme, A.; Gomez-Lor, B. Chem.-Eur. J. 2018, 24, 3576.
  (c) Sanguinet, L.; Williams, J. C.; Yang, Z. Y.; Twieg, R. J.; Mao, G. L.; Singer, K. D.; Wiggers, G.; Petschek, R. G. Chem. Mater. 2006, 18, 425.
3. [3]
  (a) Mondal, A.; Mukhopadhyay, C. ACS Comb. Sci. 2015, 17, 404.
  (b) Mondal, A.; Banerjee, B.; Bhaumik, A.; Mukhopadhyay, C. ChemCatChem 2016, 8, 1185.
  (c) Xu, H.; Chen, K.; Liu, H. W.; Wang, G. W. Org. Chem. Front. 2018, 5, 2864.
  (d) Hussein, E. M.; Moussa, Z.; Ahmed, S. A. Monatsh. Chem. 2018, 149, 2021.
4. [4]
  (a) Zhou, Y. J.; Chen, D. S.; Li, Y. L.; Liu, Y.; Wang, X. S. ACS Comb. Sci. 2013, 15, 498.
  (b) Chen, M.; Sun, N.; Liu, Y. H. Org. Lett. 2013, 15, 5574.
  (c) Allais, C.; Lieby-Muller, F.; Rodriguez, J.; Constantieux, T. Eur. J. Org. Chem. 2013, 4131.
  (d) Marquise, N.; Dorcet, V.; Chevallier, F.; Mongin, F. Org. Biomol. Chem. 2014, 12, 8138.
5. [5]
  (a) Mei, G. J.; Shi, F.; Chem. Commun. 2018, 54, 6607.
  (b) Mei, G. J.; Li, D.; Zhou, G. X.; Shi, F.; Cao, Z. Chem. Commun. 2017, 53, 10030.
  (c) Wu, J. L.; Du, B. X.; Zhang, Y. C.; He, Y. Y.; Wang, J. Y.; Wu, P.; Shi, F. Adv. Synth. Catal. 2016, 358, 2777.
  (d) Zhu, Q. N.; Zhang, Y. C.; Xu, M. M.; Sun, X. X.; Yang, X.; Shi, F. J. Org. Chem. 2016, 81, 7898.
  (e) Zhao, K.; Zhi, Y.; Shu, T.; Valkonen, A.; Rissanen, K.; Enders, D. Angew. Chem., Int. Ed. 2016, 55, 12104.
  (f) Abbaraju, S.; Ramireddy, N.; Rana, N. K.; Arman, H. J.; Zhao, C. G. Adv. Synth. Catal. 2015, 357, 2633.
6. [6]
  (a) Abdukader, A.; Zhang, Y. H.; Zhang, Z. P.; Liu, C. J. Chin. J. Org. Chem. 2016, 36, 875 (in Chinese).
  (阿布力米提·阿布都卡德尔, 张永红, 张增鹏, 刘晨江, 有机化学, 2016, 36, 875.)
  (b) Tian, W. Y.; Xu, S.; Liang, Z. W.; Sun, D. L.; Zhang, R. H. Chin. J. Org. Chem. 2016, 36, 2121 (in Chinese).
  (田文艳, 徐松, 梁中卫, 孙德立, 张荣华, 有机化学, 2016, 36, 2121.)
  (c) Hao, E. J.; Jiang, X. H.; Fu, D. D.; Wang, D. C.; Xie, M. S.; Qu, G. R.; Guo, H. M. Chin. J. Org. Chem. 2016, 36, 2746 (in Chinese).
  (郝二军, 蒋小涵, 付丹丹, 王东超, 谢明胜, 渠桂荣, 郭海明, 有机化学, 2016, 36, 2746.)
  (d) Tian, K.; Meng, J.; Gan, Y. Y.; Li, X. Q.; Wu, S. Q.; Chen, J.; Li, W.; Qi, Y. Y.; Hu, W. N.; Wang, Z. C.; Ouyang G. P. Chin. J. Org. Chem. 2018, 38, 2657 (in Chinese).
  (田坤, 孟娇, 甘宜远, 李小琴, 巫受群, 陈洁, 李文, 漆亚云, 胡伟男, 王贞超, 欧阳贵平, 有机化学, 2018, 38, 2657.)
7. [7]
  (a) Tugrak, M.; Inci Gul, H.; Sakagami, H.; Gulcin, I.; Supuran, C. T. Bioorg. Chem. 2018, 81, 433.
  (b) Jangra, H.; Chen, Q.; Fuks, E.; Zenz, I.; Mayer, P.; Ofial, A. R.; Zipse, H.; Mayr, H. J. Am. Chem. Soc. 2018, 140, 16758.
  (c) Chen, Y. R.; Ganapuram, M. R.; Hsieh, K. H.; Chen, K. H.; Karanam, P.; Vagh, S. S.; Liou, Y. C.; Lin, W. W. Chem. Commun. 2018, 54, 12702.
  (d) Xu, H.; Sha, F.; Li, Q.; Wu, X. Y. Org. Biomol. Chem. 2018, 16, 7214.
8. [8]
  (a) Wang, X. H.; Yan, C.-G. Synthesis 2014, 46, 1059.
  (b) Shi, Y. G.; Wang, X. H.; Liu, R. Z.; C. G. Yan, Chem. Commun. 2016, 52, 6280.
  (c) Zhang, Y. Y.; Han, Y.; Sun, J.; Yan, C. G. ChemistrySelect 2017, 2, 7382.
  (d) Cao, J.; Sun, J. Yan, C. G. Org. Biomol. Chem. 2018, 16, 4170.
  (e) Sun, J.; Zhang, Y.; Shi, R. G.; Yan, C. G. Org. Biomol. Chem. 2019, 17, 3978.
  (f) Liu, D.; Sun, J.; Zhang, Y.; Yan, C. G. Org. Biomol. Chem. 2019, 17, 8008.
  (g) Yang, W. J.; Fang, H. L.; Sun, J. Yan, C. G. ACS Omega 2019, 4, 13553.
  (h) Huang, Y.; Fang, H. L.; Huang, Y. X.; Sun, J.; Yan, C. G. J. Org. Chem. 2019, 84, 1912437.
9. [9]
  (a) Kröhnke, F.; Zecher, W. Angew. Chem., Int. Ed. 1962, 1, 626.
  (b) Kröhnke, F. Angew. Chem., Int. Ed. 1963, 2, 225.
  (c) Jacobs, J.; Van Hende, E.; Claessens, S.; De Kimpe, N. Curr. Org. Chem. 2011, 15, 1340.
  (d) Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642.
10. [10]
  (a) Constable, E. C.; Edwards, A. J.; Martínez-Máńez, R.; Raithby, P. R. J. Chem. Soc., Dalton Trans. 1995, 3253.
  (b) Eryazici, I.; Moorefield, C. N.; Durmus, S.; Newkone, G. R. J. Org. Chem. 2006, 71, 1009.
  (c) Tu, S. J.; Jia, R. H.; Jiang, B.; Zhang, J. Y.; Zhang, Y.; Yao, C. S.; Ji, S. J. Tetrahedron 2007, 63, 381.
11. [11]
  (a) Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435.
  (b) Sasaki, T.; Kanematsu, K.; Yukimoto, Y.; Ochiai, S. J. Org. Chem. 1971, 36, 813.
  (c) Xia, Z. Q.; Przewloka, T.; Koya, K.; Ono, M.; Chen, S. J.; Sun, L. J. Tetrahedron Lett. 2006, 47, 8817.
12. [12]
  (a) Dinica, R. M.; Druta, I. I.; Pettinari, C. Synlett 2000, 1013.
  (b) Furdui, B.; Dinica, R.; Druta, I. I.; Demeunynck, M. Synthesis 2006, 2640.
13. [13]
  (a) Zhang, X. C.; Huang, W. Y. Synthesis 1999, 1, 51.
  (b) Wu, K.; Chen, Q. Y. Synthesis 2003, 35.
  (c) Chuang, C. P.; Tsai, A. I. Synthesis 2006, 675.
14. [14]
  (a) Ruano, J. L. G.; Fraile, A.; Martín, M. R.; González, G.; Fajardo, C.; Martín-Castro, A. M. J. Org. Chem. 2011, 76, 3296.
  (b) Khlebnikov, A. F.; Golovkina, M. V.; Novikov, M. S.; Yufit, D. S. Org. Lett. 2012, 14, 3768.
  (c) Brioche, J.; Meyer, C.; Cossy, J. Org. Lett. 2015, 17, 2800.
15. [15]
  (a) Liu, Y.; Sun, J. W. J. Org. Chem. 2012, 77, 1191.
  (b) Osyanin, V. A.; Osipov, D. V.; Klimochkin, Y. N. J. Org. Chem. 2013, 78, 5505.
  (c) Wang, F. Y.; Shen, Y. M.; Hu, H. Y.; Wang, X. S.; Wu, H.; Liu, Y. J. Org. Chem. 2014, 79, 9556.
16. [16]
  (a) Allgäuer, D. S.; Mayer, P.; Mayr, H. J. Am. Chem. Soc. 2013, 135, 15216.
  (b) Allgäuer, D. S.; Mayr, H. Eur. J. Org. Chem. 2013, 6379.
  (c) Allgäuer, D. S.; Mayr, H. Eur. J. Org. Chem. 2014, 2956.
  (d) Hopf, H.; Jones, P. G.; Nicolescu, A.; Bicu, E.; Birsa, L. M.; Belei, D. Chem.-Eur. J. 2014, 20, 5565.
17. [17]
  (a) Yan, C. G.; Cai, X. M.; Wang, Q. F.; Wang, T. Y.; Zheng, M. Org. Biomol. Chem. 2007, 5, 945.
  (b) Yan, C. G.; Song, X. K.; Wang, Q. F.; Sun, J. Siemeling, U.; Bruhn, C. Chem. Commun. 2008, 1440.
  (c) Wang, Q. F.; Song, X. K.; Chen, J.; Yan, C. G. J. Comb. Chem. 2009, 11, 1007.
  (d) Wang, Q. F.; Hou, H.; Hui, L.; Yan, C. G. J. Org. Chem. 2009, 74, 7403.
  (e) Yan, C. G.; Wang, Q. F.; Song, X. K.; Sun, J. J. Org. Chem. 2009, 74, 710.
  (f) Wang, Q. F.; Hui, L.; Hou, H.; Yan, C. G. J. Comb. Chem. 2010, 12, 260.
  (g) Han, Y.; Chen, J.; Hui, L.; Yan, C. G. Tetrahedron 2010, 66, 7743.
18. [18]
  (a) Hou, H.; Zhang, Y.; Yan, C. G. Chem. Commun. 2012, 48, 4492.
  (b) Hui, L.; Li, H. Y.; Yan, C. G. Eur. J. Org. Chem. 2012, 3157.
  (c) Wu, L.; Sun, J.; Yan. C. G. Org. Biomol. Chem. 2012, 10, 9452.
  (d) Shen, G. L.; Sun, J.; Yan, C. G. Org. Biomol. Chem., 2015, 13, 10929.
  (e) Shen, G. L.; Sun, J.; Yan, C. G. RSC Adv. 2015, 5, 4475.
  (f) Liu, L. Z.; Wang, X. Y.; Sun, J.; Yan, C. G. Tetrahedron Lett. 2015, 56, 6711.
19. [19]
  (a) Banothu, J.; Basavoju, S.; Bavantula, R. J. Heterocycl. Chem. 2015, 52, 853.
  (b) Majumder, S.; Sharma, M.; Bhuyan, P. J. Tetrahedron Lett. 2013, 54, 6868.
20. [20]
  (a) Shen, G. L.; Sun, J.; Yan, C. G. Chin. J. Chem. 2016, 34, 412.
  (b) Liu, R. Z.; Shi, R. G.; Sun, J.; Yan, C. G. Org. Chem. Front. 2017, 4, 354.
  (c) Shi, R. G.; Sun, J.; Yan, C. G. ACS Omega 2017, 2, 7820.
21. [21]
  (a) Fujita, R.; Hoshino, M.; Tojyo, Y.; Kimura, A.; Hongo, H. Yakugaku Zasshi 2006, 126, 99.
  (b) Fujita, R.; Watanabe, N.; Tomisawa, H. Heterocycles 2001, 55, 435.
  (c) Fujita, R.; Hoshino, M.; Tomisawa, H. Chem. Pharm. Bull. 2006, 54, 334.
1. [1]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
2. [2]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
3. [3]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
4. [4]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
5. [5]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
6. [6]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
7. [7]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
8. [8]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
9. [9]
  Jijoe Samuel Prabagar , Kumbam Lingeshwar Reddy , Dong-Kwon Lim . Visible-light responsive gold nanoparticle and nano-sized Bi2O3-x sheet heterozygote structure for efficient photocatalytic conversion of N2 to NH3. Chinese Journal of Structural Chemistry, 2025, 44(4): 100564-100564. doi: 10.1016/j.cjsc.2025.100564
10. [10]
  Lijun Yan , Shiqi Chen , Penglu Wang , Xiangyu Liu , Lupeng Han , Tingting Yan , Yuejin Li , Dengsong Zhang . Hydrothermally stable metal oxide-zeolite composite catalysts for low-temperature NO_x reduction with improved N₂ selectivity. Chinese Chemical Letters, 2024, 35(6): 109132-. doi: 10.1016/j.cclet.2023.109132
11. [11]
  Shanyuan Bi , Jin Zhang , Dengchao Peng , Danhong Cheng , Jianping Zhang , Lupeng Han , Dengsong Zhang . Improved N₂ selectivity for low-temperature NO_x reduction over etched ZSM-5 supported MnCe oxide catalysts. Chinese Chemical Letters, 2025, 36(5): 110295-. doi: 10.1016/j.cclet.2024.110295
12. [12]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
13. [13]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
14. [14]
  Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C₃N₄/AgI._x._y heterojunction photocatalyst for simultaneous and stoichiometric production of H₂ and H₂O₂ from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
15. [15]
  Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO₃ additive to single nitrogenous component Li₂N₂O₂ SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
16. [16]
  Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194
17. [17]
  Qingwang LIU . MoS₂/Ag/g-C₃N₄ Z-scheme heterojunction: Preparation and photocatalytic performance. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 821-832. doi: 10.11862/CJIC.20240148
18. [18]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
19. [19]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
20. [20]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1350)
HTML views(229)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142