Citation:
Li Zhipeng, Chen Feiran, Wang Dongyang, Huang Xingtian, Li Yiqun. Agarose Hydrogel Entrapped Trisodium Citrate Catalyzed Multicomponent Reactions for the Synthesis of Benzopyran and Pyranopyrazole Derivatives[J]. Chinese Journal of Organic Chemistry,
;2016, 36(4): 838-843.
doi:
10.6023/cjoc201510010
-
An efficient method for the synthesis of benzopyran derivatives and pyrano[2,3-c]pyrazole derivatives via multicomponent reaction in the presence of agarose hydrogel entrapped trisodium citrate (gel-citrate) as catalyst is developed. The protocol presented here has the merits of easy preparation and handling of catalyst, environmentally benign, simple operation and convenient workup, and excellent yields. Moreover, the catalyst could be recovered and reused at least 6 cycles without apparently losing its activities.
-
-
-
[1]
[1] Strecker, A. Ann. 1850, 75, 27.
-
[2]
[2] Hantzsch, A. Ber. Dtsch. Chem. Ges. 1881, 14, 1637.
-
[3]
[3] Mannich, C.; Krösche, W. Arch. Pharm. 1912, 250, 647.
-
[4]
[4] Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8.
-
[5]
[5] (a) Ruijter, E.; Scheffelaar, R.; Orru, R. V. Angew. Chem., Int. Ed. Engl. 2011, 50, 6234.
-
[6]
(b) Wang, J.; Shen, Q.; Li, P.; Peng, Y.; Song, G. Org. Biomol. Chem. 2014, 12, 5597.
-
[7]
(c) Banfi, L.; Basso, A.; Moni, L.; Riva, R. Eur. J. Org. Chem. 2014, 2014, 2005.
-
[8]
(d) Bharti, R.; Parvin, T. RSC Adv. 2015, 5, 66833.
-
[9]
(e) Nikbakht, A.; Ramezanpour, S.; Balalaie, S.; Rominger, F. Tetrahedron 2015, 71, 6790.
-
[10]
(f) Liu, B.; Wei, E.; Lin, S.; Zhao, B.; Liang, F. Chem. Commun. 2014, 50, 6995.
-
[11]
[6] (a) Wang, Q. F.; Song, X. K.; Yan, C. G. Prog. Chem. 2009, 21, 997 (in Chinese). (王琦芳, 宋肖锴, 颜朝国, 化学进展, 2009, 21, 997.)
-
[12]
(b) Guo, H. Y.; Tian, J. J. Chin. J. Org. Chem. 2011, 31, 1752 (in Chinese). (郭红云, 田金金, 有机化学, 2011, 31, 1752.)
-
[13]
(c) Han, Y.; Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Chin. J. Org. Chem. 2012, 32, 1577 (in Chinese). (韩莹, 孙晶, 孙岩, 高红, 颜朝国, 有机化学, 2012, 32, 1577.)
-
[14]
(d) Xiao, L. W.; Peng, X. X.; Zhou, Q. X.; Kou, W.; Shi, Y. R. Chin. J. Org. Chem. 2015, 35, 1204 (in Chinese). (肖立伟, 彭晓霞, 周秋香, 寇伟, 时亚茹, 有机化学, 2015, 35, 1204.)
-
[15]
(e) Tian, J. J.; Guo, H. Y. Chin. J. Org. Chem. 2011, 31, 2009 (in Chinese). (田金金, 郭红云, 有机化学, 2011, 31, 2009.)
-
[16]
[7] (a) Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem. 1993, 28, 517.
-
[17]
(b) Zhang, G.; Zhang, Y. H.; Yan, J. X.; Chen, R.; Wang, S. L.; Ma, Y. X.; Wang, R. J. Org. Chem. 2012, 77, 878.
-
[18]
(c) Kuo, S. C.; Huang, L. J.; Nakamura, H. J. Med. Chem. 1984, 27, 539.
-
[19]
(d) Wang, J.-L.; Liu, D.; Zhang, Z.-J.; Shan, S.; Han, X.; Srinivasula, S. M.; Croce, C. M.; Alnemri, E. S.; Huang, Z. P. Natl. Acad. Sci. 2000, 97, 7124.
-
[20]
(e) Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Arch. Pharm. 2006, 339, 456.
-
[21]
[8] Litvinov, Y. M.; Shestopalov, A. A.; Rodinovskaya, L. A.; Shestopalov, A. M. J. Comb. Chem. 2009, 11, 914.
-
[22]
[9] Vasuki, G.; Kumaravel, K. Tetrahedron Lett. 2008, 49, 5636.
-
[23]
[10] Ilovaisky, A. I.; Medvedev, M. G.; Merkulova, V. M.; Elinson, M. N.; Nikishin, G. I. J. Heterocycl. Chem. 2014, 51, 523.
-
[24]
[11] Zheng, J.; Li, Y. Mendeleev Commun. 2011, 21, 280.
-
[25]
[12] Zhao, L. Q.; Li, Y. Q.; Chen, L.; Zhou, B. Chin. J. Org. Chem. 2010, 30, 124 (in Chinese). (赵丽琴, 李毅群, 陈路, 周波, 有机化学, 2010, 30, 124.)
-
[26]
[13] Guo, R. Y.; An, Z. M.; Mo, L. P.; Yang, S. T.; Liu, H. X.; Wang, S. X.; Zhang, Z. H. Tetrahedron 2013, 69, 9931.
-
[27]
[14] Elnagdi, N. M. H.; Al-Hokbany, N. S. Molecules 2012, 17, 4300.
-
[28]
[15] Bihani, M.; Bora, P. P.; Bez, G.; Askari, H. ACS Sustainable Chem. Eng. 2013, 1, 440.
-
[29]
[16] Mecadon, H.; Rohman, M. R.; Rajbangshi, M.; Myrboh, B. Tetrahedron Lett. 2011, 52, 2523.
-
[30]
[17] Wang, X. S.; Shi, D. Q.; Tu, S. J.; Yao, C. S. Synth. Commun. 2003, 33, 119.
-
[31]
[18] Tu, S. J.; Gao, Y.; Guo, C.; Shi, D. Q.; Lu, Z. S. Synth. Commun. 2002, 32, 2137.
-
[32]
[19] (a) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217.
-
[33]
(b) Buchmeiser, M. R. Chem. Rev. 2008, 109, 303.
-
[34]
[20] (a) De Vos, D. E.; Dams, M.; Sels, B. F.; Jacobs, P. A. Chem. Rev. 2002, 102, 3615.
-
[35]
(b) Thomas, J. M.; Raja, R. Acc. Chem. Res. 2008, 41, 708.
-
[36]
[21] Oded, K.; Musa, S.; Gelman, D.; Blum, J. Catal. Commun. 2012, 20, 68.
-
[37]
[22] Abu-Reziq, R.; Shenglof, M.; Penn, L.; Cohen, T.; Blum, J. J. Mol. Catal. A: Chem. 2008, 290, 30.
-
[38]
[23] Ciriminna, R.; Fidalgo, A.; Pandarus, V.; Béland, F.; Ilharco, L. M.; Pagliaro, M. ChemCatChem 2015, 7, 254.
-
[39]
[24] Diz, P.; Pernas, P.; El Maatougui, A.; Tubio, C. R.; Azuaje, J.; Sotelo, E.; Guitián, F.; Gil, A.; Coelho, A. Appl. Catal. A: Gen. 2015, 502, 86.
-
[40]
[25] Bandgar, B. P.; Uppalla, L. S. Synth. Commun. 2000, 30, 2071.
-
[41]
[26] Chaphekar, S. S.; Samant, S. D. Appl. Catal. A: Gen. 2003, 242, 11.
-
[42]
[27] Shinde, S.; Rashinkar, G.; Kumbhar, A.; Kamble, S.; Salunkhe, R. Helv. Chim. Acta 2011, 94, 1943.
-
[43]
[28] Shinde, S.; Rashinkar, G.; Salunkhe, R. J. Mol. Liq. 2013, 178, 122.
-
[44]
[29] Jadhav, S.; Kumbhar, A.; Kamble, S.; More, P.; Salunkhe, R. C. R. Chim. 2013, 16, 957.
-
[45]
[30] Natekar, R.; Samant, S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1996, 35, 1347.
-
[46]
[31] (a) Dippy, J. F. J.; Evans, R. M. J. Org. Chem. 1950, 15, 451.
-
[47]
(b) Li, Y. L.; Zhou, J. F.; Gong, G. X.; Zhu, F. X. Chin. J. Org. Chem. 2009, 29, 441 (in Chinese). (李艳伦, 周建峰, 贡桂霞, 朱凤霞, 有机化学, 2009, 29, 441.)
-
[48]
(c) Bian, Q. L.; Xu, S.; Duan, W. L. Chin. J. Org. Chem. 2015, 35, 234 (in Chinese). (边庆龙, 许胜, 段伟良, 有机化学, 2015, 35, 234.)
-
[49]
[32] Nasseri, M. A.; Sadeghzadeh, S. M. Monatsh. Chem. 2013, 144, 1551.
-
[50]
[33] Elinson, M. N.; Dorofeev, A. S.; Feducovich, S. K.; Gorbunov, S. V.; Nasybullin, R. F.; Miloserdov, F. M.; Nikishin, G. I. Eur. J. Org. Chem. 2006, 4335.
-
[51]
[34] Peng, Y.; Song, G.; Dou, R. Green Chem. 2006, 8, 573.
-
[52]
[35] Sharanina, L. G.; Promonenkov, V. K.; Marshtupa, V. P.; Pashchenko, A. V.; Puzanova, V. V.; Sharanin, Y. A.; Klyuev, N. A.; Gusev, L. F.; Gnatusina, A. P. Chem. Heterocycl. Compd. 1982, 18, 607.
-
[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]
Meihui Cai , Yi Huang , Xingxing Ma , Qiuling Song . Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction. University Chemistry, 2025, 40(11): 184-190. doi: 10.12461/PKU.DXHX202412054
-
[3]
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
-
[4]
Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
-
[5]
Xichen YAO , Shuxian WANG , Yun WANG , Cheng WANG , Chuang ZHANG . Oxygen reduction performance of self?supported Fe/N/C three-dimensional aerogel catalyst layers. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1387-1396. doi: 10.11862/CJIC.20240384
-
[6]
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
-
[7]
. . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
-
[8]
Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti3C2Tx MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
-
[9]
Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
-
[10]
Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO2 Methanation of Derived Ni-Al2O3 Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
-
[11]
Haodong JIN , Qingqing LIU , Chaoyang SHI , Danyang WEI , Jie YU , Xuhui XU , Mingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048
-
[12]
Wenruo NI , Hongpeng LI , Yun ZHANG , Yiran TIAN , Jiehui RUI , Yingcheng TONG , Xiaolin PI , Zhenyan TANG . Research progress of ruthenium alloy catalysts in hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 23-44. doi: 10.11862/CJIC.20250188
-
[13]
Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
-
[14]
Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
-
[15]
Yinuo Wang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation. University Chemistry, 2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077
-
[16]
Guanghui Wang , Chen Qian , Zhiyong Ma . Preparation and Characterization of 7H-Benzo[C]Carbazole Based Ultra-Long Organic Room Temperature Phosphorescence Material. University Chemistry, 2025, 40(11): 289-299. doi: 10.12461/PKU.DXHX202412062
-
[17]
Lianshun Zhang , Lan Bao , Ting Song , Shangying Qiao , Yifan Liu , Xianxiu Xu , Jinhuan Dong . Cu-catalyzed biheterocyclization along with sulfonyl remote migration: Access to Marinoquinoline alkaloids and 4-sulfonyl pyrrolo[2,3-c]quinolines. Chinese Chemical Letters, 2025, 36(10): 110915-. doi: 10.1016/j.cclet.2025.110915
-
[18]
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
-
[19]
Yanting HUANG , Hua XIANG , Mei PAN . Construction and application of multi-component systems based on luminous copper nanoclusters. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2075-2090. doi: 10.11862/CJIC.20240196
-
[20]
Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(1433)
- HTML views(155)
Login In
DownLoad: