Citation: LI Fei, MAO Shengxue, SUN Yue, LÜ Chengwei, AN Yue. Dipotassium Hydrogenphosphate Assisted Multi-component One-Pot Synthesis of 1, 4-Hihydropyrano[2, 3-c]pyrazole Derivatives[J]. Chinese Journal of Applied Chemistry, ;2018, 35(10): 1201-1207. doi: 10.11944/j.issn.1000-0518.2018.10.170393 shu

Dipotassium Hydrogenphosphate Assisted Multi-component One-Pot Synthesis of 1, 4-Hihydropyrano[2, 3-c]pyrazole Derivatives

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China

Corresponding author: LÜ Chengwei, chengweilv@126.com
Received Date: 2 November 2017
Revised Date: 8 December 2017
Accepted Date: 15 December 2017

Fund Project: Liaoning Province, the Doctoral Scientific Research Foundation 20141100Supported by the National Natural Science Foundation of China(No.21403100), Liaoning Province, the Doctoral Scientific Research Foundation(No.20141100), the Key Laboratory of Education Department of Liaoning Province(No.L201683656)the National Natural Science Foundation of China 21403100the Key Laboratory of Education Department of Liaoning Province L201683656

Figures(1)

Catalytic one-pot four-component reaction is an ideal strategy for efficient and facile synthesis of pyrano[2, 3-c]pyrazoles. The efficacy of dipotassium hydrogenphosphate(K₂HPO₄·3H₂O) as a cheap and readily accessible catalyst for the synthesis of 1, 4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile derivatives via one-pot four-component reaction of ethyl acetoacetate, hydrazine hydrate, aryl aldehydes, and malononitrile was described in this paper. These multi-component condensations proceeded smoothly in aqueous polyethylene glycol(PEG-200) and the corresponding products were obtained in 88%~98% yields. This improved protocol eliminates the problems associated with expensive complex catalyst and tedious purification procedures.
- dipotassium hydrogenphosphate,
- 1, 4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile,
- multi-component reaction,
- synthesis,
- aqueous polyethylene glycol 200
1. [1]
  Kanagaraj K, Pitchumani K. Solvent-Free Multicomponent Synthesis of Pyranopyrazoles:Per-6-amino-b-cyclodextrin as a Remarkable Catalyst and Host[J]. Tetrahedron Lett, 2010,51(25):3312-3316. doi: 10.1016/j.tetlet.2010.04.087
2. [2]
  Saha M, Das B, Pal A K. Synthesis of Pyran Derivatives under Ultrasound Irradiation Using Ni Nanoparticles as Reusable Catalysts in Aqueous Medium[J]. C R Chim, 2013,16(12):1079-1085. doi: 10.1016/j.crci.2013.05.012
3. [3]
  Bian L, Xu J, Xie L. Three-component Synthesis of 2-Amino-3-cyano-5-oxo-4-perfluoroalkyl-5, 6, 7, 8-tetrahydro-4H-chromene Derivatives[J]. Tetrahedron, 2013,69(30):6121-6128. doi: 10.1016/j.tet.2013.05.053
4. [4]
  Paul S, Pradhan K, Ghosh S. Uncapped SnO₂ Quantum Dot Catalyzed Cascade Assembling of Four Components:A Rapid and Green Approach to the Pyrano[2, 3-c]pyrazole and Spiro-2-oxindole Derivatives[J]. Tetrahedron, 2014,70(36):6088-6099. doi: 10.1016/j.tet.2014.02.077
5. [5]
  Moosavi-Zare A R, Zolfigol M A, Mousavi-Tashar A. Synthesis of Pyranopyrazole Derivatives by in Situ Generation of Trityl Carbocation under Mild and Neutral Media[J]. Res Chem Intermed, 2016,42(10):7305-7312. doi: 10.1007/s11164-016-2537-4
6. [6]
  Sabry N M, Mohamed H M, Khattab E S. Synthesis of 4H-chromene, Coumarin, 12H-chromeno[2, 3-d]pyrimidine Derivatives and Some of Their Antimicrobial and Cytotoxicity Activities[J]. Eur J Med Chem, 2011,46(2):765-772. doi: 10.1016/j.ejmech.2010.12.015
7. [7]
  Costa M, Proenca F. 2-Aryl-1, 9-dihydrochromeno[3, 2-d]imidazoles:A Facile Synthesis from Salicylaldehydes and Arylideneaminoacetonitrile[J]. Tetrahedron, 2011,67(10):1799-1804. doi: 10.1016/j.tet.2011.01.035
8. [8]
  Yao C, Jiang B, Li T. Design and an Efficient Synthesis of Natural Product-based Cyclopenta[b]pyran Derivatives with Potential Bioactivity[J]. Bioorg Med Chem Lett, 2011,21(1):599-601. doi: 10.1016/j.bmcl.2010.09.076
9. [9]
  Zonouz A M, Eskandari I, Khavasi H R. A Green and Convenient Approach for the Synthesis of Methyl 6-Amino-5-cyano-4-aryl-2, 4-dihydropyrano[2, 3-c]pyrazole-3-carboxylates via a One-Pot, Multi-component Reaction in Water[J]. Tetrahedron Lett, 2012,53(41):5519-5522. doi: 10.1016/j.tetlet.2012.08.010
10. [10]
  Mandha S R, Siliveri S, Alla M. Eco-friendly Synthesis and Biological Evaluation of Substituted Pyrano[2, 3-c]pyrazoles[J]. Bioorg Med Chem Lett, 2012,22(16):5272-5278. doi: 10.1016/j.bmcl.2012.06.055
11. [11]
  LI Xiaojun, GUO Hongyun. One-Pot Synthesis of 1, 4-dihydropyrano[2, 3-c]pyrazoles Catalyzed by Basic Ionic Liquids[J]. Chinese J Org Chem, 2012,32(1):127-132.
12. [12]
  Mecadon H, Rohman Md R, Rajbangshi M. 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[J]. Tetrahedron Lett, 2011,52(19):2523-2525. doi: 10.1016/j.tetlet.2011.03.036
13. [13]
  WANG Yinglei, LUO Jun, XING Tantan. Synthesis of Pyrano[2, 3-c]pyrazoles Catalyzed by Poly(Ethylene Glycol) Bridged Triethylamine Functionalized Dication Ionic Liquid[J]. Chinese J Org Chem, 2013,33(9):2016-2021.
14. [14]
  Zhou C F, Li J J, Su W K. Morpholine Triflate Promoted One-Pot, Four-Component Synthesis of Dihydropyrano[2, 3-c]pyrazoles[J]. Chinese Chem Lett, 2016,27(11):1686-1690. doi: 10.1016/j.cclet.2016.05.010
15. [15]
  Wu M, Feng Q, Wan D. Ctacl as Catalyst for Four-Component, One-Pot Synthesis of Pyranopyrazole Derivatives in Aqueous Medium[J]. Synth Commun, 2013,43(12):1721-1726. doi: 10.1080/00397911.2012.666315
16. [16]
  Moosavi-Zare A R, Zolfigol M A, Noroozizadeh E. Synthesis of 6-Amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1, 4-dihydropyrano[2, 3-c]pyrazoles Using Disulfonic Acid Imidazolium Chloroaluminate as a Dual and Heterogeneous Catalyst[J]. New J Chem, 2013,37(12):4089-4094. doi: 10.1039/c3nj00629h
17. [17]
  Brahmachari G, Banerjee B. Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-cyano-4H-pyrans and Pyran-annulated Heterocyclic Scaffolds via an Eco-friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-catalyst[J]. ACS Sustainable Chem Eng, 2014,2(3):411-422. doi: 10.1021/sc400312n
18. [18]
  Ilovaisky A I, Medvedev M G, Merkulova V M. Green Approach to the Design of Functionalized Medicinally Privileged 4-Aryl-1, 4-dihydropyrano[2, 3-c]-pyrazole-5-carbonitrile Scaffold[J]. J Heterocycl Chem, 2014,51(2):523-526. doi: 10.1002/jhet.v51.2
19. [19]
  Tamaddon F, Alizadeh M. A Four-component Synthesis of Dihydropyrano[2, 3-c]pyrazoles in a New Water-Based Worm-Like Micellar Medium[J]. Tetrahedron Lett, 2014,55(26):3588-3591. doi: 10.1016/j.tetlet.2014.04.122
20. [20]
  Ebrahimipour S Y, Ranjabr Z R, Kermani E T. A Mixed-ligand Ternary Complex of Nickel(Ⅱ):Synthesis, Characterization and Catalytic Investigation for the Synthesis of Pyranopyrazoles[J]. Trans Met Chem, 2015,40(1):39-45. doi: 10.1007/s11243-014-9887-9
21. [21]
  Elinson M N, Nasybullin R F, Nikishin G I. Sodium Acetate Catalyzed Tandem Knoevenagel Michael Multicomponent Reaction of Aldehydes, 2-Pyrazolin-5-ones, and Cyano-functionalized C-H Acids:Facile and Efficient Way to 3-(5-Hydroxypyrazol-4-yl)-3-aryl-propionitriles[J]. C R Chim, 2013,16(9):789-794. doi: 10.1016/j.crci.2013.03.003
22. [22]
  Elinson M N, Nasybullin R F, Ryzhkov F V. Solvent-free and On-water' Multicomponent Assembling of Aldehydes, 3-Methyl-2-pyrazoline-5-one, and Malononitrile:Fast and Efficient Approach to Medicinally Relevant Pyrano[2, 3-c]pyrazole Scaffold[J]. Monatsh Chem, 2015,146(4):631-635. doi: 10.1007/s00706-014-1318-2
23. [23]
  Vekariya R H, Patel K D, Pate H. A Green and One-pot Synthesis of a Library of 1, 4-Dihydropyrano[2, 3-c]-pyrazole-5-carbonitrile Derivatives Using Thiourea Dioxide(TUD) as an Efficient and Reusable Organocatalyst[J]. Res Chem Intermed, 2016,42(5):4683-4696. doi: 10.1007/s11164-015-2308-7
24. [24]
  Moosavi-Zare A R, Zolfigol M A, Salehi-Moratab R. Catalytic Application of 1-(Carboxymethyl)pyridinium Iodide on the Synthesis of Pyranopyrazole Derivatives[J]. J Mol Catal A:Chem, 2016,415:144-150. doi: 10.1016/j.molcata.2016.02.003
25. [25]
  Huang X, Li Z, Wang D. Bovine Serum Albumin:An Efficient and Green Biocatalyst for the One-Pot Four-Component Synthesis of Pyrano[2, 3-c]pyrazoles[J]. Chinese J Catal, 2016,37(9):1461-1467. doi: 10.1016/S1872-2067(15)61088-9
26. [26]
  Vekariya R H, Patel K D, Patel H D. Fruit Juice of Citrus Limon as a Biodegradable and Reusable Catalyst for Facile, Eco-friendly and Green Synthesis of 3, 4-Disubstituted Isoxazol-5(4H)-ones and Dihydropyrano[2, 3-c]-pyrazole Derivatives[J]. Res Chem Intermed, 2016,42(10):7559-7579. doi: 10.1007/s11164-016-2553-4
27. [27]
  Zakeri M, Nasef M M, Kargaran T. Synthesis of Pyrano[2, 3-c]pyrazoles by Ionic Liquids under Green and Eco-safe Conditions[J]. Res Chem Intermed, 2017,43(2):717-728. doi: 10.1007/s11164-016-2648-y
28. [28]
  WANG Huiyan, ZOU Yi, TAO Chuanzhou. One-pot Four-component Synthesis of Dihydropyrano[2, 3-c]pyrazoles under Ultrasound Irradiations[J]. Chinese J Org Chem, 2011,31(12):2161-2166.
29. [29]
  Zou Y, Hu Y, Liu H. An Efficient and Green Synthesis of 6-Amino-3-phenyl-4-aryl-1, 4-dihydropyrano[2, 3-c]pyrazole-5-carbonitrile Derivatives under Ultrasound Irradiation in Aqueous Medium[J]. J Heterocycl Chem, 2013,50(5):1174-1179.
30. [30]
  Dekamin M G, Alikhani M, Emami A. An Effcient Catalyst and Solvent-Free Method for the Synthesis of Medicinally Important Dihydropyrano[2, 3-c]pyrazole Derivatives Using Ball Milling Technique[J]. J Iran Chem Soc, 2016,13(3):591-596. doi: 10.1007/s13738-015-0793-7
31. [31]
  Upadhyay A, Sharma L K, Singh V K. Electrochemically Induced One Pot Synthesis of 1, 4-Dihydropyrano[2, 3-c]-pyrazole-5-carbonitrile Derivatives via a Four Component-tandem Strategy[J]. Tetrahedron Lett, 2017,58(13):1245-1249. doi: 10.1016/j.tetlet.2017.01.049
32. [32]
  Iravani N, Keshavarz M, Kish H A S. Tin Sulfide Nanoparticles Supported on Activated Carbon as an Efficient and Reusable Lewis Acid Catalyst for Three-Component One-Pot Synthesis of 4H-Pyrano[2, 3-c]pyrazole Derivatives[J]. Chinese J Catal, 2015,36(4):626-633. doi: 10.1016/S1872-2067(14)60284-9
33. [33]
  Kumar H, Kaur K. Effect of Dipotassium Hydrogen Phosphate on Thermodynamic Properties of Glycine and L-Alanine in Aqueous Solutions at Different Temperatures[J]. J Chem Thermodyn, 2012,53:86-92. doi: 10.1016/j.jct.2012.04.020
34. [34]
  Zhang X, Li K, Li H. Dipotassium Hydrogen Phosphate as Reducing Agent for the Efficient Reduction of Graphene Oxide Nanosheets[J]. J Colloid Interface Sci, 2013,409(11):1-7.
35. [35]
  Kumar H, Singla M, Mittal H. Volumetric, Acoustic and Viscometric Behaviour of Dipotassium Hydrogen Phosphate and Disodium Hydrogen Phosphate in Aqueous Solution of N-Acetyl Glycine at Different Temperatures[J]. J Chem Thermodyn, 2016,94:204-220. doi: 10.1016/j.jct.2015.10.017
36. [36]
  Saikia A, Barthakur M G, Borthakur M. Conjugate Base Catalysed One-Pot Synthesis of Pyrazoles from β-Formyl Enamides[J]. Tetrahedron Lett, 2006,47(1):43-46. doi: 10.1016/j.tetlet.2005.10.145
37. [37]
  Balalaie S, Abdolmohammadi S, Bijanzadeh H R. Diammonium Hydrogen Phosphate as a Versatile and Efficient Catalyst for the One-Pot Synthesis of Pyrano[2, 3-d]pyrimidinone Derivatives in Aqueous Media[J]. Mol Diversity, 2008,12(2):85-91. doi: 10.1007/s11030-008-9079-7
38. [38]
  Mandhane P G, Joshi R S, Nagargoje D R. Ultrasound-Promoted Greener Approach to Synthesize α-Hydroxy Phosphonates Catalyzed by Potassium Dihydrogen Phosphate under Solvent-free Condition[J]. Tetrahedron Lett, 2010,51(11):1490-1492. doi: 10.1016/j.tetlet.2010.01.031
39. [39]
  Damavandi S, Sandaroos R. KHPO₄/Ultrasonic Irradiation Catalyzed Multicomponent Synthesis of Aminocyanopyrano[3, 2-b]indole[J]. Res Chem Intermed, 2013,39(3):1251-1256. doi: 10.1007/s11164-012-0681-z
40. [40]
  Bodaghifard M A, Solimannejad M, Asadbegi S. Mild and Green Synthesis of Tetrahydrobenzopyran, Pyranopyrimidinone and Polyhydroquinoline Derivatives and DFT Study on Product Structures[J]. Res Chem Intermed, 2016,42(2):1165-1179. doi: 10.1007/s11164-015-2079-1
41. [41]
  Abdolmohammadi S, Balalaie S. Novel and Efficient Catalysts for the One-Pot Synthesis of 3, 4-Dihydropyrano[c]chromene Derivatives in Aqueous Media[J]. Tetrahedron Lett, 2007,48(18):3299-3303. doi: 10.1016/j.tetlet.2007.02.135
42. [42]
  LYU Chengwei, LIU Yanhang, WANG Jiajing. Potassium Dihydrogen Phosphate Catalyzed Yonemitsu Condensation for Synthesis of 5-[(Indol-3-yl)-arylmethyl]-2, 2-dimethyl-1, 3-dioxane-4, 6-dine Derivatives[J]. Chinese J Appl Chem, 2015,32(12):1371-1378. doi: 10.11944/j.issn.1000-0518.2015.12.150165
43. [43]
  Gao S, Xiao D, Yang Y. KH₂PO₄ Promoted Practical and Environmentally Friendly Preparation of Coumarin-3-carboxylic Acids under Solvent-free Condition[J]. Heterocycles, 2016,92(9):1698-1705. doi: 10.3987/COM-16-13510
44. [44]
  Yü S J, Wu S, Zhao X M. Green and Efficient Synthesis of Acridine-1, 8-diones and Hexahydroquinolines via a KH₂PO₄ Catalyzed Hantzsch-type Reaction in Aqueous Ethanol[J]. Res Chem Intermed, 2017,43(5):3121-3130. doi: 10.1007/s11164-016-2814-2
45. [45]
  Kumar A, Rao M S, Rao V K. Sodium Dodecyl Sulfate-assisted Synthesis of 1-(Benzothiazolylamino)methyl-2-naphthols in Water[J]. Aust J Chem, 2010,63(11):1538-1540. doi: 10.1071/CH10209
46. [46]
  Chanda A, Fokin V V. Organic Synthesis "On Water"[J]. Chem Rev, 2009,109(2):725-748. doi: 10.1021/cr800448q
47. [47]
  Bhardwaj M, Sahi S, Mahajan H. Novel Heterogeneous Catalyst Systems Based on Pd(0) Nanoparticles onto Amine Functionalized Silica-Cellulose Substrates[Pd(0)-EDA/SCS]:Synthesis, Characterization and Catalytic Activity Toward C-C and C-S Coupling Reactions in Water under Limiting Basic Conditions[J]. J Mol Catal A:Chem, 2015,408:48-59. doi: 10.1016/j.molcata.2015.07.005
48. [48]
  Brahmachari G. Room Temperature One-pot Green Synthesis of Coumarin-3-carboxylic Acids in Water:A Practical Method for the Large-Scale Synthesis[J]. ACS Sustainable Chem Eng, 2015,3(9):2350-2358. doi: 10.1021/acssuschemeng.5b00826
49. [49]
  Xiao J, Wen H, Wang L. Catalyst-Free Dehydrative SN₁-Type Reaction of Indolyl Alcohols with Diverse Nucleophiles "On Water"[J]. Green Chem, 2016,18(4):1032-1037. doi: 10.1039/C5GC01838B
50. [50]
  Candeias N R, Branco L C, Gois P M P. More Sustainable Approaches for the Synthesis of N-Based Heterocycles[J]. Chem Rev, 2009,109(6):2703-2802. doi: 10.1021/cr800462w
51. [51]
  Wang X C, Yang G J, Quan Z J. Synthesis of 2-Substituted Pyrimidines via Cross-coupling Reaction of Pyrimidin-2-yl Sulfonates with Nucleophiles in Polyethylene Glycol 400[J]. Synlett, 2010,41(46):1657-1660.
52. [52]
  Reddy M V, Kim J S, Lim K T. Polyethylene Glycol (PEG-400):An Efficient Green Reaction Medium for the Synthesis of Benzo[4, 5] imidazo[1, 2-a]-pyrimido[4, 5-d]pyrimidin-4(1H)-ones under Catalyst-free Conditions[J]. Tetrahedron Lett, 2014,55(47):6459-6462. doi: 10.1016/j.tetlet.2014.09.135
53. [53]
  Khan M N, Karamthulla S, Choudhury L H. Ultrasound Assisted Multicomponent Reactions:A Green Method for the Synthesis of Highly Functionalized Selenopyridines Using Reusable Polyethylene Glycol as Reaction Medium[J]. RSC Adv, 2015,5(28):22168-22172. doi: 10.1039/C5RA02403J
54. [54]
  Kumar M A, Babu M F S, Srinivasulu K. Polyethylene Glycol in Water:A Simple and Environment Friendly Media for Strecker Reaction[J]. J Mol Catal A:Chem, 2007,265(1-2):268-271. doi: 10.1016/j.molcata.2006.10.030
55. [55]
  Engel-Andreasen J, Shimpukade B, Ulven T. Selective Copper Catalysed Aromatic N-Arylation in Water[J]. Green Chem, 2013,15(2):336-340. doi: 10.1039/C2GC36589H
56. [56]
  Nagaraju A, Ramulu B J, Shukla G. Catalyst-free One-pot Four-component Domino Reactions in Water-PEG-400:Highly Efficient and Convergent Approach to Thiazoloquinoline Scaffolds[J]. Green Chem, 2015,17(2):950-958. doi: 10.1039/C4GC01431F
57. [57]
  Zhang J, Yao J, Liu J. Four-component Reaction Between Naphthols, Substituted β-Nitrostyrenes, Substituted Benzaldehydes and Ammonium Acetate in Water-PEG-400:An Approach to Construct Polysubstituted Naphthofuranamines[J]. RSC Adv, 2015,5(60):48580-48585. doi: 10.1039/C5RA07642K
58. [58]
  Santaniello E, Ferraboschi P, Sozzani P. Efficient and Selective Oxidation of Alcohols by Potassium Dichromate Solutions[J]. Synthesis, 1980,1980(8):646-647. doi: 10.1055/s-1980-29154
59. [59]
  Wang L, Huang M, Zhu X. Polyethylene Glycol(PEG-200)-Promoted Sustainable One-Pot Three-Component Synthesis of 3-Indole Derivatives in Water[J]. Appl Catal A:General, 2013,454:160-163. doi: 10.1016/j.apcata.2012.12.008
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沈阳化工大学材料科学与工程学院沈阳 110142