Citation: Mahnaz Farahi, Bahador Karami, Iman Sedighimehr, Hamideh Mohamadi Tanuraghaj. An environmentally friendly synthesis of 1,4-dihydropyrano [2,3-c]pyrazole derivatives catalyzed by tungstate sulfuric acid[J]. Chinese Chemical Letters, ;2014, 25(12): 1580-1582. doi: 10.1016/j.cclet.2014.07.012 shu

An environmentally friendly synthesis of 1,4-dihydropyrano [2,3-c]pyrazole derivatives catalyzed by tungstate sulfuric acid

1.
Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran

Corresponding author: Bahador Karami,
Received Date: 27 May 2014
Available Online: 25 June 2014

An efficient three-component synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles via a reaction between 3-methyl-1-phenyl-2-pyrazolin-5-one, aromatic aldehydes and malononitrile using tungstate sulfuric acid as a catalyst was described. Mild conditions, good to excellent yields, easily available catalyst and easy work-up are the key features of this method.
- 6-Amino-4-aryl-5-cyano-3-methyl-1-,
- phenyl-1,4-dihydropyrano[2,3-c]pyrazoles,
- 3-Methyl-1-phenyl-2-pyrazolin-5-one,
- Aromatic aldehyde,
- Malononitrile,
- Tungstate sulfuric acid
1. [1]
  [1] A.K. Elziaty, O.E.A. Mostafa, E.A. El-Bordany, M. Nabil, H.M.F. Madkour, Access to new pyranopyrazoles and related heterocycles, Int. J. Sci. Eng. Res. 5 (2014) 727-735.
2. [2]
  [2] C.B. Sangani, D.C. Mungra, M.P. Patel, R.G. Patel, Synthesis and in vitro antimicrobial screening of newpyrano[4,3-b]pyran derivatives of 1H-pyrazole, Chin. Chem. Lett. 23 (2012) 57-60.
3. [3]
  [3] S. Hatakeyama, N. Ochi, H. Numata, S. Takano, A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (-)-methyl elenolate, Chem. Commun. (1988) 1202-1204.
4. [4]
  [4] F. Karc, Synthesis of some novel pyrazolo[51-c][1,2,4]triazine derivatives and investigation of their absorption spectra, Dyes Pigm. 76 (2008) 97-103.
5. [5]
  [5] H. Kiyani, H.A. Samimi, F. Ghorbani, S. Esmaieli, One-pot, four-component synthesis of pyrano[2,3-c]pyrazoles catalyzed by sodium benzoate in aqueous medium, Curr. Chem. Lett. 2 (2013) 197-206.
6. [6]
  [6] D. Shi, J. Mou, Q. Zhuang, et al., Three-component one-pot synthesis of 1,4-dihydropyrano [2,3-c] pyrazole derivatives in aqueous media, Synth. Commun. 34 (2004) 4557-4563.
7. [7]
  [7] M.E.A. Zaki, Synthesis of novel fused heterocycles based on pyrano[2,3-c]pyrazole, Molecules 3 (1998) 71-79.
8. [8]
  [8] T.S. Jin, R.Q. Zhao, T.S. Li, An one-pot three-component process for the synthesis of 6-amino-4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles in aqueous media, ARKIVOK xi (2006) 176-182.
9. [9]
  [9] K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivative, Chin. J. Catal. 34 (2013) 2245-2254.
10. [10]
  [10] M. Farahi, B. Karami, M. Azari, Tungstate sulfuric acid as an efficient catalyst for the synthesis of benzoxazoles and benzothiazoles under solvent-free conditions, Compt. Rend. Chim. 16 (2013) 1029-1034.
11. [11]
  [11] B. Karami, M. Montazerzohouri, Tungstate sulfuric acid (TSA)/KMnO4 as a novel heterogeneous system for rapid deoximation, Molecules 11 (2006) 720-725.
12. [12]
  [12] B. Karami, Z. Haghighijou, M. Farahi, S. Khodabakhshi, One-pot synthesis of dihydropyrimidine-thione derivatives using tungstate sulfuric acid (TSA) as a recyclable catalyst, Phosphorus Sulfur Silicon Relat. Elem. 187 (2012) 754-761.
13. [13]
  [13] B. Karami, M. Farahi, S. Khodabakhshi, Rapid synthesis of novel and known coumarin-3-carboxylic acids using stannous chloride dihydrate under solventfree conditions, Helv. Chim. Acta 95 (2012) 455-460.
14. [14]
  [14] S.W. Kshirsagar, N.R. Patil, S.D. Samant, Mg-Al hydrotalcite as a first heterogeneous basic catalyst for the synthesis of 4H-pyrano[2,3-c]pyrazoles through a four-component reaction, Synth. Commun. 41 (2011) 1320-1325.
15. [15]
  [15] H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in aqueous medium, Tetrahedron Lett. 52 (2011) 2523-2525.
16. [16]
  [16] M.M. Heravi, A. Ghods, F. Derikvand, K. Bakhtiari, F.F. Bamoharram, H₁₄[NaP₅W₃₀O₁₁₀] catalyzed one-pot three-component synthesis of dihydropyrano[2,3-c]pyrazole and pyrano[2,3-d]pyrimidine derivatives, J. Iran. Chem. Soc. 7 (2010) 615-620.
17. [17]
  [17] M.M. Heravi, N. Javanmard, H.A. Oskooie, B. Baghernejad, A facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives using p-toluene sulfonic acid in aqueous media, G.U. J. Sci. 24 (2011) 227-231.
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]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
3. [3]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
4. [4]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
5. [5]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
6. [6]
  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
7. [7]
  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
8. [8]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
9. [9]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
10. [10]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
11. [11]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
12. [12]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
13. [13]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
14. [14]
  Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb₂O₆/Nitrogen-Enriched C₃N₅ S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
15. [15]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
16. [16]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
17. [17]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
18. [18]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
19. [19]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(702)
HTML views(21)

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