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. shu

H6P2W18O62·18H2O: A green and reusable catalyst for one-pot synthesis of pyrano[4,3-b]pyrans in water

  • Corresponding author: Balwant S. Keshwal, 
  • Received Date: 28 March 2013
    Available Online: 25 June 2013

  • 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.
  • 加载中
    1. [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]

      [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]

      [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]

      [4] I.V. Kozhevinikov, Heteropoly acids and related compounds as catalysts for fine chemical synthesis, Catal. Rev. Sci. Eng. 37 (1995) 311.

    5. [5]

      [5] Y. Izumi, R. Hasebe, K. Urabe, Catalysis by heterogeneous supported heteropoly acid, J. Catal. 84 (1983) 402.

    6. [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]

      [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]

      [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]

      [9] F. Liu, T. Evans, B.C. Das, Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates, Tetrahedron Lett. 49 (2008) 1578.

    10. [10]

      [10] J. Zhu, H. Bienayme, Multicomponent Reactions, 1st ed., Wiley-VCH, Weinheim, 2005.

    11. [11]

      [11] A. Domling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3168.

    12. [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [21] M.Z. Piao, K. Imafuku, Convenient synthesis of amino-substituted pyranopyranones, Tetrahedron Lett. 38 (1997) 5301.

    22. [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [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]

      [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.

  • 加载中
    1. [1]

      Yulong ShiFenbei ChenMengyuan WuXin ZhangRunze MengKun WangYan WangYuheng MeiQionglu DuanYinghong LiRongmei GaoYuhuan LiHongbin DengJiandong JiangYanxiang WangDanqing 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. [2]

      Huiju CaoLei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466

    3. [3]

      Ruolin CHENGYue WANGXiyao NIUHuagen LIANGLing LIUShijian LU . Efficient photothermal catalytic CO2 cycloaddition over W18O49/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424

    4. [4]

      Ruolin CHENGHaoran WANGJing RENYingying MAHuagen 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

    5. [5]

      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

    6. [6]

      Chunru ZhaoYi LiuShilong LiXiang WuJinghai Liu . PVP decorated H3.78V6O13 microspheres assembled by nanosheets for aqueous zinc ion batteries at variable work temperature. Chinese Chemical Letters, 2025, 36(6): 110185-. doi: 10.1016/j.cclet.2024.110185

    7. [7]

      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

    8. [8]

      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

    9. [9]

      Shuwen SUNGaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399

    10. [10]

      Xu-Hui YueXiang-Wen ZhangHui-Min HeLei QiaoZhong-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

    11. [11]

      Tong ZhouXue LiuLiang ZhaoMingtao QiaoWanying Lei . Efficient Photocatalytic H2O2 Production and Cr(Ⅵ) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-0. doi: 10.3866/PKU.WHXB202309020

    12. [12]

      Hualin JiangWenxi YeHuitao ZhenXubiao LuoVyacheslav FominskiLong YePinghua 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

    13. [13]

      Xinyi ZhangKai RenYanning LiuZhenyi GuZhixiong HuangShuohang ZhengXiaotong WangJinzhi GuoIgor V. ZatovskyJunming CaoXinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057

    14. [14]

      Lei FengZe-Min ZhuYing YangZongbin HeJiafeng ZouMan-Bo LiYan ZhaoZhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029

    15. [15]

      Guoqiang ChenZixuan ZhengWei ZhongGuohong WangXinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C3N4 Nanosheets for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021

    16. [16]

      Wei ZhongDan ZhengYuanxin OuAiyun MengYaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C3N4 Photocatalyst for Highly-Efficient H2O2 Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005

    17. [17]

      Xiao XiaoBiao ChenJia-Wei LiJun-Bo ZhengXu WangHang ZhaoFen-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

    18. [18]

      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

    19. [19]

      Yi YangXin ZhouMiaoli GuBei ChengZhen WuJianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn2S4 photocatalyst for H2O2 production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064

    20. [20]

      Qiang FengJindong HaoYa HuRong FuWei WeiDong Yi . Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor. Chinese Chemical Letters, 2025, 36(6): 110582-. doi: 10.1016/j.cclet.2024.110582

Metrics
  • PDF Downloads(0)
  • Abstract views(999)
  • HTML views(6)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return