Citation: Deepika Rajguru, Balwant S. Keshwal, Shubha Jain. H6P2W18O62·18H2O: A green and reusable catalyst for one-pot synthesis of pyrano[4,3-b]pyrans in water[J]. Chinese Chemical Letters, ;2013, 24(11): 1033-1036.
-
A convenient, efficient and environmentally benign procedure has been developed for the synthesis of pyrano[4,3-b]pyran derivatives via a one-pot, three-component reaction of 4-hydroxy-6-methylpyran-2-one, aldehydes and malononitrile in water using H6P2W18O62·18H2O as catalyst. Reusability of the catalyst and reaction media, short reaction times and easy isolation of products are some added advantages of the present methodology.
-
-
[1]
[1] S. Allameh, M.M. Heravi, M.M. Hashemi, et al., Synthesis of 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives using heteropolyacids as green, heterogeneous and recyclable catalysts, Chin. Chem. Lett. 22 (2011) 131.
-
[2]
[2] S. Allameh, M.M. Hashemi, M.M. Heravi, et al., Synthesis of quinazolin-4(3H)-one derivatives using heteropolyacids as heterogeneous and recyclable catalysts, Asian J. Chem. 23 (2011) 1588.
-
[3]
[3] M.H. Alizadeh, H. Razavi, F.F. Bamoharram, et al., The oxidative cleavage of carbon tin bond catalyzed by heteropolyacids ofmolybdenum, J. Mol. Catal. 206 (2003) 89.
-
[4]
[4] I.V. Kozhevinikov, Heteropoly acids and related compounds as catalysts for fine chemical synthesis, Catal. Rev. Sci. Eng. 37 (1995) 311.
-
[5]
[5] Y. Izumi, R. Hasebe, K. Urabe, Catalysis by heterogeneous supported heteropoly acid, J. Catal. 84 (1983) 402.
-
[6]
[6] H. Soeda, T. Okuhara, M. Misono, Selective alkylation of p-xylene with 2-methylpropene by 12-tungstophosphoric acid, Chem. Lett. 23 (1994) 909.
-
[7]
[7] M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Three component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in the presence of H6P2W18O62 18H2O as a green and recyclable catalyst, Catal. Commun. 10 (2008) 272.
-
[8]
[8] C.O. Kappe, Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog, Acc. Chem. Res. 33 (2000) 879.
-
[9]
[9] F. Liu, T. Evans, B.C. Das, Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates, Tetrahedron Lett. 49 (2008) 1578.
-
[10]
[10] J. Zhu, H. Bienayme, Multicomponent Reactions, 1st ed., Wiley-VCH, Weinheim, 2005.
-
[11]
[11] A. Domling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3168.
-
[12]
[12] C.J. Li, Organic reactions in aqueous media-with a focus on carbon-carbon bond formation, Chem. Rev. 93 (1993) 2023.
-
[13]
[13] A. Meijer, S. Otto, J.B.F.N. Engberts, Effects of the hydrophobicity of the reactants on Diels-Alder reactions in water, J. Org. Chem. 63 (1998) 8989.
-
[14]
[14] M. Uher, V. Konecny, O. Rajniakove, Synthesis of 5-hydroxy-2-hydroxymethyl-4H-pyran-4-one derivatives with pesticide activity, Chem. Pap. 48 (1994) 282.
-
[15]
[15] M. Perez-Perez, J. Balzarini, J. Rozenski, et al., Synthesis and antiviral activity of phosphonate derivatives of enantiomeric dihydro-2H-pyranyl nucleosides, Bioorg. Med. Chem. Lett. 5 (1995) 1115.
-
[16]
[16] X. Fan, D. Feng, Y. Qu, et al., Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents, Bioorg. Med. Chem. Lett. 20 (2010) 809.
-
[17]
[17] M.D. Aytemir, U. Calis, M. Ozalp, Synthesis and evaluation of anticonvulsant and antimicrobial activities of 3-hydroxy-6-methyl-2-substituted 4H-pyran-4-one derivatives, Arch. Pharm. 337 (2004) 281.
-
[18]
[18] S. Wang, G.W.A. Milne, X. Yang, et al., Discovery of novel, non-peptide HⅣ-1 protease inhibitors by pharmacophore searching, J. Med. Chem. 39 (1996) 2047.
-
[19]
[19] L. Pochet, C. Doucet, M. Schynts, et al., Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of a-chymotrypsin: significance of the "aromatic" nature of the novel ester-type coumarin for strong inhibitory activity, J. Med. Chem. 39 (1996) 2579.
-
[20]
[20] A. Mazumder, S. Wang, N. Neamati, et al., Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease, J. Med. Chem. 39 (1996) 2472.
-
[21]
[21] M.Z. Piao, K. Imafuku, Convenient synthesis of amino-substituted pyranopyranones, Tetrahedron Lett. 38 (1997) 5301.
-
[22]
[22] E.V. Stoyanov, I.C. Ivanov, D. Heber, General method for the preparation of substituted 2-amino-4H,5H-pyrano[4,3-b]pyran-5-ones and 2-amino-4H-pyrano[3,2-c]pyridine-5-ones, Molecules 5 (2000) 19.
-
[23]
[23] D.Q. Shi, L.H. Niu, Q.Y. Zhuhang, One-pot three-component synthesis of pyrano[3,2-c]pyran-5-one derivatives in aqueous medium, Chin. J. Org. Chem. 28 (2008) 1633.
-
[24]
[24] X.S. Wang, J.X. Zhou, Z.S. Zeng, et al., One-pot synthesis of pyrano[3,2-c]pyran derivatives catalyzed by KF/Al2O3, Arkivoc 11 (2006) 107.
-
[25]
[25] M. Seifi, H. Sheibani, High surface areaMgOas a highly effective heterogeneous base catalyst for three-component synthesis of tetrahydrobenzopyran and 3,4-dihydropyrano[c]chromene derivatives in aqueous media, Catal. Lett. 126 (2008) 275.
-
[26]
[26] A. Shaabani, S. Samadi, Z. Badri, et al., Ionic liquid promoted efficient and rapid onepot synthesis of pyran annulated heterocyclic systems, Catal. Lett. 104 (2005) 1.
-
[27]
[27] J.M. Khurana, B. Nand, P. Saluja, DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H-benzo[g]-chromenes in aqueous medium, Tetrahedron 66 (2010) 5637.
-
[28]
[28] A. Shaabani, S. Samadi, A. Rahmati, One-pot, three-component condensation reaction in water: an efficient and improved procedure for the synthesis of pyran annulated heterocyclic systems, Synth. Commun. 37 (2007) 491.
-
[29]
[29] D. Rajguru, B.S. Keshwal, S. Jain, Solvent-free, green and efficient synthesis of pyrano[4,3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents, Med. Chem. Res. (2013), http://dx.doi.org/10.1007/s00044-013-0586-4.
-
[1]
-
-
[1]
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
-
[2]
Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
-
[3]
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
-
[4]
Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
-
[5]
Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
-
[6]
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
-
[7]
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
-
[8]
Xu-Hui Yue , Xiang-Wen Zhang , Hui-Min He , Lei Qiao , Zhong-Ming Sun . Synthesis, chemical bonding and reactivity of new medium-sized polyarsenides. Chinese Chemical Letters, 2024, 35(7): 108907-. doi: 10.1016/j.cclet.2023.108907
-
[9]
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
-
[10]
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
-
[11]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[12]
Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H2O2 system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
-
[13]
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
-
[14]
Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C3N4纳米片及其高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
-
[15]
Xiao Xiao , Biao Chen , Jia-Wei Li , Jun-Bo Zheng , Xu Wang , Hang Zhao , Fen-Er Chen . Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow. Chinese Chemical Letters, 2024, 35(7): 109280-. doi: 10.1016/j.cclet.2023.109280
-
[16]
Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
-
[17]
Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H3PW12O40高效催化MgH2储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
-
[18]
Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe2O3/TiO2 heterojunction for enhanced photo-Fenton activity with low H2O2 consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
-
[19]
Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
-
[20]
Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(724)
- HTML views(5)