Citation: Sun Jing, Cao Jun, Han Ying, Yan Chao-Guo. Progress in Multicomponent Reactions Involving 1, 3-Indanedione[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4122-4146. doi: 10.6023/cjoc202005003 shu

Progress in Multicomponent Reactions Involving 1, 3-Indanedione

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002

Corresponding author: Yan Chao-Guo, cgyan@yzu.edu.cn
Received Date: 2 May 2020
Revised Date: 11 June 2020
Available Online: 8 July 2020
Fund Project: the National Natural Science Foundation of China 21572196Project supported by the National Natural Science Foundation of China (No. 21572196)

Figures(74)

1, 3-Indanedione is one of typical cyclic 1, 3-dicarbonyl compounds with one methylene unit, two carbonyl groups and fused phenyl ring. Thus, it has three contiguous reactive electrophilic and nucleophilic sites. On the other hand, 1, 3-indanedione undergoes homopolymerization to form several cyclic compounds with polycarbonyl groups under acidic or basic medium. 2-Arylidene-1, 3-indanediones derived from condensation of aromatic aldehydes with 1, 3-indanedione are also reactive α, β-unsaturated carbonyl compounds. Therefore, 1, 3-indanedione has diverse reactivities and is the key substrate in domino and multicomponent reactions. It has been widely employed to construct various spiro, bridged and fused cyclic compounds. The recent achievements on multicomponent reactions involving 1, 3-indanedione from the structures of the target compounds and the important applications on the syntheses of biologically important indanone-containing carbocyclic and heterocyclic compounds are summarized. The effects of catalyst, reaction mechanism, experimental results, reaction characteristics and limitations are briefly discussed. At last, the future development on the diverse reactions of 1, 3-indanedione is also prospected.
- 1, 3-indanedione,
- heterocycle,
- multicomponent reaction,
- cycloaddition reaction,
- Domino reaction
1. [1]
  Khan, F. A.; Maalik, A. Trop. J. Pharm. Res. 2015, 14, 1937. doi: 10.4314/tjpr.v14i10.28
2. [2]
  (a) Tu, S. J.; Jiang, B.; Zhang, J. Y.; Jia, R. H.; Zhang, Y.; Yao, C. S. Org. Biomol. Chem. 2006, 4, 3980.
  (b) Majumder, S.; Sharma, M.; Bhuyan, P. J. Tetrahedron Lett. 2013, 54, 6868.
  (c) Ahadi, S.; Moafi, L.; Feiz, A.; Bazgir, A. Tetrahedron 2011, 67, 3954.
  (d) Liang, B.; Kalidindi, S.; Porco, J. A. Stephenson, C. Org. Lett. 2010, 12, 572.
  (e) Nishiyama, T.; Shiotsu, S.; Tsujita, H. Polym. Degrad. Stab. 2002, 76, 435.
3. [3]
  Sharma, L. K.; Kimb, K. B.; Elliott, G. I. Green Chem. 2011, 13, 1546. doi: 10.1039/c1gc15164a
4. [4]
  Asadi, S.; Mohammadi Z. G. Mol. Diversity 2015, 20, 111.
5. [5]
  (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
  (b) Peppe, C.; Chagas, R. P.; Burrow, R. A. J. Organomet. Chem. 2008, 693, 3441.
  (c) Ren, Z.; Cao, W.; Ding, W.; Wang, Y.; Wang, L. Synth. Commun. 2004, 34, 3785.
  (d) Arai, S.; Nakayama, K.; Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 63, 9572.
  (e) Miyagawa, T.; Tatenuma, T.; Tadokoro, M.; Satoh, T. Tetrahedron 2008, 64, 5279.
6. [6]
  Wang, G. W.; Gao, J. Org. Lett. 2009, 11, 2385. doi: 10.1021/ol900451d
7. [7]
  Yang, S. X.; Chen, J.; Wu, X. Y.; Deng, H. M.; Shao, M.; Zhang, H.; Cao, W. G. Chin. J. Org. Chem. 2010, 30, 1521(in Chinese).
8. [8]
  Das, U.; Tsai, Y. L.; Lin, W. W. Org. Biomol. Chem. 2013, 11, 44. doi: 10.1039/C2OB26943K
9. [9]
  Nemcsok, T.; Rapi, Z.; Bagi, P.; Olah, A.; Keglevich, G.; Bako, P. Catal. Lett. 2020, 150, 930. doi: 10.1007/s10562-019-03013-0
10. [10]
  Banothu, J.; Basavoju, S.; Bavantula, R. J. Heterocycl. Chem. 2015, 52, 853. doi: 10.1002/jhet.2059
11. [11]
  Liu, R. Z.; Shi, R. G.; Sun, J.; Yan, C. G. Org. Chem. Front. 2017, 4, 354. doi: 10.1039/C6QO00615A
12. [12]
  Jiang, Y. H.; Sun, J.; Sun, Q.; Yan, C. G. Asian J. Org. Chem. 2017, 6, 862. doi: 10.1002/ajoc.201700125
13. [13]
  Hu, F.; Wei, Y.; Shi, M. Tetrahedron 2012, 68, 7911. doi: 10.1016/j.tet.2012.07.013
14. [14]
  Zhan, G.; Shi, M. L.; He, Q.; Lin, W. J.; Ouyang, Q.; Du, W.; Chen, Y. C. Angew. Chem., Int. Ed. 2016, 55, 2147. doi: 10.1002/anie.201510825
15. [15]
  Yang, Y.; Jiang, Y.; Du, W.; Chen, Y. C. Chem.-Eur. J. 2020, 26, 1754. doi: 10.1002/chem.201904930
16. [16]
  Lu, Y. L.; Sun, J.; Jiang, Y. H.; Yan, C. G. RSC Adv. 2016, 6, 50471. doi: 10.1039/C6RA02358D
17. [17]
  Ramachary, D. B.; Reddy, T. P.; Kumar, A. S. Org. Biomol. Chem. 2016, 14, 6517. doi: 10.1039/C6OB01009A
18. [18]
  Manjappa, K. B.; Peng, Y. T.; Jhang, W. F.; Yang, D. Y. Tetrahedron 2016, 72, 853. doi: 10.1016/j.tet.2015.12.056
19. [19]
  Shen, G. L.; Sun, J.; Yan, C. G. Chin. J. Chem. 2016, 34, 412. doi: 10.1002/cjoc.201500896
20. [20]
  Jin, G.; Sun, J.; Yan, C. G. RSC Adv. 2016, 6, 84379. doi: 10.1039/C6RA16838H
21. [21]
  Shi, R. G.; Sun, J.; Yan, C. G. ACS Omega 2017, 2, 7820. doi: 10.1021/acsomega.7b01391
22. [22]
  Liu, C. Z.; Han, Y.; Qi, W. J.; Yan, C. G. Heterocycl. Commun. 2016, 22, 301.
23. [23]
  Qi, W. J.; Han, Y.; Liu, C. Z.; Yan, C. G. Synthesis 2016, 48, 4465. doi: 10.1055/s-0036-1588309
24. [24]
  Chen, L.; Sun, J.; Huang, Y.; Zhang, Y.; Yan, C. G. Sci. Rep. 2017, 7, 12418. doi: 10.1038/s41598-017-12361-z
25. [25]
  Huang, Y.; Sun, J.; Yan, C. G. ChemistrySelect 2017, 2, 10496. doi: 10.1002/slct.201702162
26. [26]
  Zhao, B.; Liang, H. W.; Yang, J.; Yang, Z.; Wei, Y. ACS Catal. 2017, 7, 5612. doi: 10.1021/acscatal.7b01876
27. [27]
  Yu, J.; Chien, H.; Lin, Y.; Karanam, P.; Chen, Y.; Lin, W. W. Chem. Commun. 2018, 54, 9921. doi: 10.1039/C8CC05693E
28. [28]
  Chen, Y. R.; Ganapuram, M. R.; Hsieh, K. H.; Chen, K. H.; Karanam, P.; Vagh, S.; Liou, Y. C.; Lin, W. W. Chem. Commun. 2018, 54, 12702. doi: 10.1039/C8CC07271J
29. [29]
  Duan, J. D.; Mao, Y. Y.; Zhang, L.; Zhu, N.; Fang, Z.; Guo, K. Adv. Synth. Catal. 2020, 362, 695. doi: 10.1002/adsc.201901333
30. [30]
  Huang, Y.; Fang, H. L.; Huang, Y. X.; Sun, J.; Yan, C. G. J. Org. Chem. 2019, 84, 12437. doi: 10.1021/acs.joc.9b01920
31. [31]
  (a) Qiu, X. L.; Meng, W. D.; Qing, F. L. Tetrahedron 2004, 60, 6711.
  (b) Qiu, X. L.; Qing, F. L. Eur. J. Org. Chem. 2011, 3261.
  (c) Smits, R.; Cadicamo, C. D.; Burger, K.; Koksch, B. Chem. Soc. Rev. 2008, 37, 1727.
  (d) Acena, J. L.; Simon-Fuentes, A.; Fustero, S. Curr. Org. Chem. 2010, 14, 928.
  (e) March, T. L.; Johnston, M. R.; Duggan, P. J.; Gardiner, J. Chem. Biodiversity 2012, 9, 2410.
  (f) Remete, A. M.; Nonn, M.; Fustero, S.; Fülöp, F.; Kiss, L. Tetrahedron 2018, 74, 6367.
32. [32]
  (a) Yoder, N. C.; Jumar, K. Chem. Soc. Rev. 2002, 31, 335.
  (b) Akcay, G.; Kumar, K. J. Fluorine Chem. 2009, 130, 1178.
  (c) Salwiczek, M.; Nyakatura, E. K.; Gerling, U. I. M.; Ye, S.; Koksch, B. Chem. Soc. Rev. 2012, 41, 2135.
  (d) Marsh, E.; Neil, G. Acc. Chem. Res. 2014, 47, 2878.
  (e) Berger, A. A.; Völler, J. S.; Budisa, N.; Koksch, B. Acc. Chem. Res. 2017, 50, 2093.
  (f) Huhmann, S.; Koksch, B. Eur. J. Org. Chem. 2018, 3667.
33. [33]
  Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Acena, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422. doi: 10.1021/acs.chemrev.5b00392
34. [34]
  Smits, R. C.; Cadicamo, D.; Burger, K.; Koksch, B. Chem. Soc. Rev. 2008, 37, 1727. doi: 10.1039/b800310f
35. [35]
  Winter, M.; Faust, K.; Himmelsbach, M.; Waser, M. Org. Biomol. Chem. 2019, 17, 5731. doi: 10.1039/C9OB01134J
36. [36]
  Li, Y. M.; Zhang, H. K.; Wei, R.; Miao, Z. W. Adv. Synth. Catal. 2017, 359, 4158. doi: 10.1002/adsc.201701013
37. [37]
  Rajawat, A.; Khandelwal, S.; Kumar, M. RSC Adv. 2014, 4, 5105. doi: 10.1039/c3ra44600j
38. [38]
  Khandelwal, S.; Tailor, Y. K.; Kumar, M. J. Mol. Liq. 2016, 215, 345. doi: 10.1016/j.molliq.2015.12.015
39. [39]
  Tailor, Y. K.; Khandelwal, S.; Jain, H. K. Curr. Org. Synth. 2015, 12, 484. doi: 10.2174/157017941204150522190425
40. [40]
  Khandelwal, S.; Rajawat, A.; Tailor, K. Y.; Kumar, M. Comb. Chem. High Throughput Screening 2014, 17, 763. doi: 10.2174/1386207317666141016125218
41. [41]
  Liu, P.; Hao, J. W.; Mo, L. P.; Zhang, Z. H. RSC Adv. 2015, 5, 48675. doi: 10.1039/C5RA05746A
42. [42]
  Rushell, E.; Tailor, Y. K.; Khandelwal, S.; Verma, K.; Agarwal, M.; Kumar, M. New J. Chem. 2019, 43, 12462. doi: 10.1039/C9NJ02694K
43. [43]
  Yang, S. M.; Karanam, P.; Wang, M.; Jang, Y. J.; Yeh, Y. S.; Tseng, P. Y.; Ganapuram, M. R.; Liou, Y. C.; Lin, W. W. Chem. Commun. 2019, 55, 13981.
44. [44]
  Majumder, S.; Sharma, M.; Bhuyan, P. J. Tetrahedron Lett. 2013, 54, 6868. doi: 10.1016/j.tetlet.2013.10.023
45. [45]
  Wang, X. H.; Yan, C. G. Synthesis 2014, 46, 1059. doi: 10.1055/s-0033-1340815
46. [46]
  Addla, D.; Bhima; Sridhar, B.; Devi, A.; Kantevari, S. Bioorg. Med. Chem. Lett. 2012, 22, 7475. doi: 10.1016/j.bmcl.2012.10.042
47. [47]
  Yang, W. J.; Zhang, J.; Sun, J.; Yan, C. G. Eur. J. Org. Chem. 2016, 5423.
48. [48]
  Mohammad, H. R.; Mohammad, H. M.; Razieh, M. J. Chem. Res. 2017, 41, 430. doi: 10.3184/175815517X14981249895596
49. [49]
  Pelit, E. Chem. Sci. Int. J. (CSIJ) 2017, 20, 1.
50. [50]
  Li, M. M.; Duan, C. S.; Yu, Y. Q.; Xu, D. Z. Dyes Pigm. 2018, 150, 202. doi: 10.1016/j.dyepig.2017.12.007
51. [51]
  Maleki, A.; Yeganeh, N. N. Appl. Organomet. Chem. 2017, 31, e3814. doi: 10.1002/aoc.3814
52. [52]
  Rather, R. A.; Siddiqui, Z. N. Appl. Organomet. Chem. 2019, 33, e5176.
53. [53]
  Leila, Z. F.; Mohammad, N.; Samira, N. K. J. Organomet. Chem. 2019, 894, 18. doi: 10.1016/j.jorganchem.2019.05.004
54. [54]
  Hernandez, J. O.; Lizarazo, C.; Cobo, J.; Portilla, J. RSC Adv. 2019, 9, 27318. doi: 10.1039/C9RA04682H
55. [55]
  Bagheri, M.; Gholamzadeh, P.; Ziarani, G. M.; Badiei, A. Res. Chem. Intermed. 2019, 45, 3301. doi: 10.1007/s11164-019-03740-4
56. [56]
  Mohammadi, A.; Mohammad, B.; Nasri, S. RSC Adv. 2019, 9, 16525. doi: 10.1039/C9RA03214B
57. [57]
  Luo, Q.; Huang, R.; Xiao, Q.; Kong, L. B.; Lin, J.; Yan, S. J. ACS Omega 2019, 4, 6637. doi: 10.1021/acsomega.9b00407
58. [58]
  Gao, Y.; Liu, D. H.; Fu, Z. Q.; Huang, W. Org. Lett. 2019, 21, 926. doi: 10.1021/acs.orglett.8b03892
59. [59]
  Cao, J.; Sun, J.; Yan, C. G. Org. Biomol. Chem. 2018, 16, 4170. doi: 10.1039/C8OB00144H
60. [60]
  Chang, Y. P.; Gurubrahamam, R.; Chen, K. M. Org. Lett. 2015, 17, 2908. doi: 10.1021/acs.orglett.5b01040
61. [61]
  Reddy, G. M.; Ko, C. T.; Hsieh, K. H.; Lee, C. J.; Das, U.; Lin, W. W. J. Org. Chem. 2016, 81, 2420. doi: 10.1021/acs.joc.5b02921
62. [62]
  Yang, R. Y.; Sun, J.; Yan, C. G. ACS Omega 2018, 3, 5406. doi: 10.1021/acsomega.8b00464
63. [63]
  Champetter, P.; Castillo-Aguilera, O.; Taillier, C. Briere, J. F.; Dalla, V.; Oudeyer, S.; Comesse, S. Eur. J. Org. Chem. 2019, 7703.
64. [64]
  Yang, W. J.; Fang, H. L.; Sun, J.; Yan, C. G. ACS Omega 2019, 4, 13553. doi: 10.1021/acsomega.9b01960
65. [65]
  Sun, J.; Yang, R. Y.; Zhan, S. C.; Yan, C. G. ChemistrySelect 2019, 4, 10100. doi: 10.1002/slct.201902619
66. [66]
  Zhan, S. C.; Sun, J.; Liu, R. Z.; Yan, C. G. Org. Biomol. Chem. 2020, 18, 163. doi: 10.1039/C9OB02013F
67. [67]
  Ye, R.; Yan, C. G. Eur. J. Org. Chem. 2019, 5882.
68. [68]
  (a) Kohlhagen, G.; Paull, K.; Cushman, M.; Nagafuji, P.; Pommier, Y. Mol. Pharmacol. 1998, 54, 50.
  (b) Strumberg, D.; Pommier, Y.; Paull, K.; Jayaraman, M.; Nagafuji, P.; Cushman, M. J. Med. Chem. 1999, 42, 446.
  (c) Cushman, M.; Jayaraman, M.; Vroman, J. A.; Fukunaga, A. K.; Fox, B. M.; Kohlhagen, G.; Strumberg, D.; Pommier, Y. J. Med. Chem. 2000, 43, 3688.
69. [69]
  (a) Nagarajan, M.; Morrell, A.; Ioanoviciu, A.; Antony, S.; Kohlhagen, G.; Agama, K.; Hollingshead, M.; Pommier, Y.; Cushman, M. J. Med. Chem. 2006, 49, 6283.
  (b) Morrell, A.; Placzek, M.; Parmley, S.; Antony, S.; Dexheimer, T. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2007, 50, 4419.
  (c) Kiselev, E.; DeGuire, S.; Morrell, A.; Agama, K.; Dexheimer, T. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2011, 54, 6106.
  (d) Kiselev, E.; Agama, K.; Pommier, Y.; Cushman, M. J. Med. Chem. 2012, 55, 1682.
  (e) Nguyen, T. X.; Abdelmalak, M.; Marchand, C.; Agama, K.; Pommier, Y.; Cushman, M. J. Med. Chem. 2015, 58, 3188.
  (f) Lv, P. C.; Elsayed, M. S. A.; Agama, K.; Marchand, C.; Pommier, Y.; Cushman, M. J. Med. Chem. 2016, 59, 4890.
70. [70]
  Huang, C. Y.; Kavala, V.; Kuo, C. W.; Konala, A.; Yang, T. H.; Yao, C. F. J. Org. Chem. 2017, 82, 1961. doi: 10.1021/acs.joc.6b02814
71. [71]
  Abdelrazek, F. M.; Metz, P.; Jaeger, A. J. Heterocycl. Chem. 2019, 56, 1939. doi: 10.1002/jhet.3572
72. [72]
  Eisert, B.; Geiss, F. Chem. Ber. 1961, 94, 929. doi: 10.1002/cber.19610940410
73. [73]
  Drew, M. G. B.; Vickery, B.; Willey, G. R. J. Chem. Soc., Perkin Trans. 2 1982, 1297.
74. [74]
  Bello, K. A.; Cheng, L.; Griffiths, J. J. Chem. Soc., Perkin Trans. 2 1987, 815.
75. [75]
  Payili, N.; Rekula, S. R.; Aitha, A.; Mutha, A. K.; Naidu, C. G.; Yennam, S. Org. Biomol. Chem. 2019, 17, 9442. doi: 10.1039/C9OB01900F
76. [76]
  Zhang, L.; Duan, J. D.; Xu, G. C.; Ding, X. J.; Mao, Y. Y.; Rong, B. S.; Zhu, N.; Fang, Z.; Li, Z. J.; Guo. K. J. Org. Chem. 2020, 85, 2532. doi: 10.1021/acs.joc.9b03238
77. [77]
  Abdelrazek, F. M.; Metz, P.; Jaeger, A. J. Heterocycl. Chem. 2019, 56, 1939. doi: 10.1002/jhet.3572
78. [78]
  Amsharov, K. Y.; Jansen, M. J. Org. Chem. 2008, 73, 2931. doi: 10.1021/jo7027008
79. [79]
  Cao, J.; Sun, J.; Yan, C. G. Org. Biomol. Chem. 2019, 17, 9008. doi: 10.1039/C9OB01779H
80. [80]
  Wu, M. C.; Yang, J. H, ; Luo, F.; Cheng, C. G.; Zhu, G. G. Org. Biomol. Chem. 2019, 17, 5684. doi: 10.1039/C9OB00836E
81. [81]
  Cao, J.; Sun, J.; Yan, C. G. J. Org. Chem. 2020, 85, 2168. doi: 10.1021/acs.joc.9b02911
82. [82]
  Chen, R.; Xu, S.; Fan, X.; Li, H.; Tang, Y.; He, Z. J. Org. Biomol. Chem. 2015, 13, 398. doi: 10.1039/C4OB01927J
83. [83]
  Zhang, Y. Y.; Han, Y.; Sun, J.; Yan, C. G. ChemistrySelect 2017, 2, 7382. doi: 10.1002/slct.201701348
84. [84]
  Yang, W. J.; Zhang, J.; Sun, J.; Xie, Y. J.; Yan, C. G. Tetrahedron 2017, 73, 3387. doi: 10.1016/j.tet.2017.05.019
85. [85]
  Manick, A. D.; Salgues, B.; Parrain, J. L.; Zaborova, E.; Fages, F.; Amatore, M.; Commeiras L. Org. Lett. 2020, 22, 1894. doi: 10.1021/acs.orglett.0c00235
86. [86]
  Liegeois, J. F.; Bruhwyler, J.; Rogister, F.; Delarge, J. Curr. Med. Chem. 1995, 1, 471.
87. [87]
  Peters, J. U.; Galley, G.; Jacobsen, H.; Czech, C.; DavidPierson, P.; Kitas, E. A.; Ozmen, L. Bioorg. Med. Chem. Lett. 2007, 17, 5918. doi: 10.1016/j.bmcl.2007.07.078
88. [88]
  Fuwa, H.; Takahashi, Y.; Konno, Y.; Watanabe, N.; Miyashita, H.; Sasaki, M.; Natsugari, H.; Kan, T.; Fukuyama, T.; Tomita, T.; Iwatsubo, T. ACS Chem. Biol. 2007, 2, 408. doi: 10.1021/cb700073y
89. [89]
  Shi, R. G.; Wang, X. H.; Liu, R. Z.; Yan, C. G. Chem. Commun. 2016, 52, 6280. doi: 10.1039/C6CC00525J
90. [90]
  Samineni, R.; Srihari, P.; Mehta, G. Org. Lett. 2016, 18, 2832. doi: 10.1021/acs.orglett.6b01078
91. [91]
  Yao, Q. Y.; Kong, L. K.; Wang, M. D.; Yuan, Y.; Sun, R. Z.; Li, Y. Z. Org. Lett. 2018, 20, 1744. doi: 10.1021/acs.orglett.8b00206
1. [1]
  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
2. [2]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
3. [3]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
9. [9]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
15. [15]
  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
16. [16]
  Yuan Chun , Lijun Yang , Jinyue Yang , Wei Gao . Ideological and Political Design of BZ Oscillatory Reaction Experiment. University Chemistry, 2024, 39(2): 72-76. doi: 10.3866/PKU.DXHX202308072
17. [17]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
18. [18]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
19. [19]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
20. [20]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

Get Citation

PDF

XML

Metrics

PDF Downloads(139)
Abstract views(5913)
HTML views(1168)

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