Citation: CHEN Chen, RUAN Hongli, LÜ Le, SONG Zhixi, LÜ Chengwei, AN Yue. Synthesis of Pyridazine Derivatives by Base-Catalyzed Three-Component Reaction of Aldehyde, Malononitrile and Phthalhydrazide[J]. Chinese Journal of Applied Chemistry, ;2020, 37(5): 502-511. doi: 10.11944/j.issn.1000-0518.2020.05.190311 shu

Synthesis of Pyridazine Derivatives by Base-Catalyzed Three-Component Reaction of Aldehyde, Malononitrile and Phthalhydrazide

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

Corresponding author: LÜ Chengwei, chengweilv@126.com
Received Date: 19 November 2019
Revised Date: 6 January 2020
Accepted Date: 20 February 2020

Fund Project: the Department of Science and Technology of Liaoning Province 2019-ZD-0470the Department of Science and Technology of Liaoning Province 2019-MS-215Supported by the Department of Science and Technology of Liaoning Province(No.2019-MS-215, No.2019-ZD-0470)

Figures(3)

Catalytic amount of organic base triethylamine (Et₃N) or inorganic base dipotassium hydrogen phosphate (K₂HPO₄·3H₂O) is proved to effectively promote the three components reaction of aromatic aldehyde, malononitrile and phthalhydrazide under conventional heating conditions. As expected, introduction of water is favorable to the reaction. A series of 1H-pyrazole [1, 2-b]pyridazine-5, 10-diones derivatives was synthesized in the yield of 39%~97%. Both catalysts are soluble in water, and introduction of water also facilitate the separation of the catalyst after reaction. This approach also has advantages of mild reaction conditions, green environmental protection, simple operation and convenient post-treatment.
- trimethylamine,
- dipotassium hydrogen phosphate trihydrate,
- base catalytic,
- multi-component reactions,
- phthalazines derivatives
1. [1]
  Soheilizad M, Adib M, Sajjadifar S. One-Pot and Solvent-Free Synthesis of Aliphatic and Aromatic 1H-Indazolo[2, 1-b]phthalazinetriones Catalyzed by Boron Sulfonic Acid[J]. Monatsh Chem, 2014,145(8):1353-1356. doi: 10.1007/s00706-014-1194-9
2. [2]
  Sinkkonen J, Ovcharenko V, Zelenin K N. ¹H and ¹³C NMR Study of 1-Hydrazino-2, 3-Dihydro-1H-Pyrazolo[1, 2-a]pyridazine-5, 8-Diones and -1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Diones and Their Ring-Chain Tautomerism[J]. Eur J Org Chem, 2002,2002(13):2046-2053. doi: 10.1002/1099-0690(200207)2002:13<2046::AID-EJOC2046>3.0.CO;2-C
3. [3]
  Grasso S, De Sarro G, De Sarro A. Synthesis and Anticonvulsant Activity of Novel and Potent 6, 7-Methylenedioxyphthalazin-1(2H)-Ones[J]. J Med Chem, 2000,43(15):2851-2859. doi: 10.1021/jm001002x
4. [4]
  EL-Sakka S, Soliman A H, Imam A. Synthesis, Antimicrobial Activity and Electron Impactof Mass Spectra of Phthalazine-1, 4-Dione Derivatives[J]. Afinidad, 2009,66(540):167-172.
5. [5]
  Ryu C K, Park R E, Ma M Y. Synthesis and Antifungal Activity of 6-Arylamino-Phthalazine-5, 8-Diones and 6, 7-Bis(Arylthio)-Phthalazine-5, 8-Diones[J]. Bioorg Med Chem Lett, 2007,17(9):2577-2580. doi: 10.1016/j.bmcl.2007.02.003
6. [6]
  Li J, Zhao Y F, Yuan X Y. Synthesis and Anticancer Activities of Novel 1, 4-Disubstituted Phthalazines[J]. Molecules, 2006,11(7):574-582. doi: 10.3390/11070574
7. [7]
  Franklin E C. Heterocyclic Nitrogen Compounds.I.Pentacyclic Compounds[J]. Chem Rev, 1935,16(3):305-361. doi: 10.1021/cr60055a001
8. [8]
  Bergstrom F W. Heterocyclic Nitrogen Compounds.Part IIA.Hexacyclic Compounds:Pyridine, Quinoline, and Isoquinoline[J]. Chem Rev, 1944,35(2):77-277. doi: 10.1021/cr60111a001
9. [9]
  Lichtenthaler F W. Unsaturated O- and N-heterocycles from Carbohydrate Feedstocks[J]. Acc Chem Res, 2002,35(9):728-737. doi: 10.1021/ar010071i
10. [10]
  Litvinov V P. Multicomponent Cascade Heterocyclisation as a Promising Route to Targeted Synthesis of Polyfunctional Pyridines[J]. Russ Chem Rev, 2003,72(1):69-85. doi: 10.1070/RC2003v072n01ABEH000764
11. [11]
  Wu H, Chen X M, Wan Y. Synthesis and Luminescence of 7-Amino-2H-Indazolo[2, 1-b]phthalazine-1, 6, 11(13H)-Triones Catalyzed by Silica Sulfuric Acid[J]. Lett Org Chem, 2009,6(3):219-223.
12. [12]
  Tayebee R, Abdizadeh M F, Maleki B. Heteropolyacid-Based Ionic Liquid[Simp]₃PW₁₂O₄₀ Nanoparticle as a Productive Catalyst for the One-Pot Synthesis of 2H-Indazolo[2, 1-b]phthalazine-Triones under Solvent-Free Conditions[J]. J Mol Liq, 2017,241:447-455. doi: 10.1016/j.molliq.2017.06.033
13. [13]
  Mirhosseini-Eshkevari B, Ghasemzadeh M A, Safaei-Ghomi J. An Efficient and Green One-Pot Synthesis of Indazolo[1, 2-b]phthalazinetriones via Three-Component Reaction of Aldehydes, Dimedone, and Phthalhydrazide Using Fe₃O₄@SiO₂ Core-Shell Nanoparticles[J]. Res Chem Intermed, 2015,41(10):7703-7714. doi: 10.1007/s11164-014-1854-8
14. [14]
  Saha M, Phukan S, Jamatia R. Solvent Free, Ni-Nanoparticle Catalyzed Greener Synthesis and Photophysical Studies of Novel 2H-Indazolo[2, 1-b]phthalazine-Trione Derivatives[J]. RSC Adv, 2013,3(6):1714-1721. doi: 10.1039/C2RA22396A
15. [15]
  Shaterian H R, Ghashang M, Feyzi M. Silica Sulfuric Acid as an Efficient Catalyst for the Preparation of 2H-Indazolo[2, 1-b]phthalazine-Triones[[J]. Appl Catal A-Gen, 2008,345(2):128-133. doi: 10.1016/j.apcata.2008.04.032
16. [16]
  Ghahremanzadeh R, Shakibaei G I, Bazgir A. An Efficient One-Pot Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Dione Derivatives[J]. Synlett, 2008(8):1129-1132.
17. [17]
  Raghuvanshi D S, Singh K N. A Highly Efficient Green Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Dione Derivatives and Their Photophysical Studies[J]. Tetrahedron Lett, 2011,52(43):5702-5705. doi: 10.1016/j.tetlet.2011.08.111
18. [18]
  Sabour F H, Nasr-Esfahani M, Mohammadpoor-Baltork I. A Convenient Approach for the Synthesis of Various Derivatives of Pyrazolo[1, 2-b]phthalazinediones in the Presence of an Efficient Supported Basic Ionic Liquid at Ambient Temperature and Solvent-Free Media[J]. J Iran Chem Soc, 2018,15(3):671-683. doi: 10.1007/s13738-017-1267-x
19. [19]
  Piltan M. Preparation of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Diones Using ZrO₂ Nanoparticles as a Catalyst under Solvent-Free Conditions[J]. Heterocycl Commun, 2017,23(5):401-403.
20. [20]
  Tayebee R, Maleki B. A New Simple Method for the Preparation of PbO Nanoparticles and Implementation of an Efficient and Reusable Catalytic System for the Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Diones[J]. J Iran Chem Soc, 2017,14(6):1179-1188. doi: 10.1007/s13738-017-1068-2
21. [21]
  Sangani C B, Makwana J A, Duan Y T. Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Dione Derivatives:Assessment of Their Antimicrobial, Antituberculosis and Antioxidant Activity[J]. Res Chem Intermed, 2016,42(3):2101-2117. doi: 10.1007/s11164-015-2138-7
22. [22]
  Vafaee A, Davoodnia A, Pordel M. An Efficient and High-Yielding One-Pot Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Diones Catalyzed by Sodium Hydrogen Carbonate under Solvent-Free Conditions[J]. Orient J Chem, 2015,31(4):2153-2158. doi: 10.13005/ojc/310437
23. [23]
  Nabid M R, Rezaei S J T, Ghahremanzadeh R. Ultrasound-Assisted One-Pot, Three-Component Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine- 5, 10-Diones[J]. Ultrason Sonochem, 2010,17(1):159-161.
24. [24]
  Saiprathima P, Srinivas K, Rao M M. "On water" Catalysis:An expeditious Approach for the Synthesis of Quaternary Centered 3-Hydroxy-3-(nitromethyl)indolin-2-one Derivatives[J]. Green Chem, 2015,17:2339-2343. doi: 10.1039/C4GC02203C
25. [25]
  Liu X, Zhang S B, Zhu H. Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water[J]. J Org Chem, 2018,83(19):11703-11711. doi: 10.1021/acs.joc.8b01644
26. [26]
  Lv C W, Wang J J, Li F. Efficient Synthesis of 2-Amino-3-Cyano-4H-Pyran Derivatives via a Non-catalytic One-Pot Three-Component Reaction[J]. Res Chem Intermed, 2018,44(2):1035-1043. doi: 10.1007/s11164-017-3151-9
27. [27]
  Yu 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, 2016,43(5):3121-3130.
28. [28]
  RUAN Hongli, ZHANG Jingyuan, SUN Sai. N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids[J]. Chinese J Org Chem, 2017,37(8):2139-2144.
29. [29]
  XIAO Di, ZHENG Wang, WEI Xiaoyu. Choline Chioride Promoted Synthesis of Coumarin-3-carboxylic Acids[J]. Chinese J Appl Chem, 2017,34(11):1295-1300. doi: 10.11944/j.issn.1000-0518.2017.11.170005
30. [30]
  Zhang X, Li K, Li H. Dipotassium Hydrogen Phosphate as Reducing Agent for the Efficient Reduction of Graphene Oxide Nanosheets[J]. J Colloid Interfaace Sci, 2013,409(11):1-7.
31. [31]
  Lv C W, Gao S, Xiao D. 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
32. [32]
  Kidwai M, Chauhan R. A Rapid and an Efficient Route to the One-Pot, Multicomponent Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine-5, 10-Dione Ring Systems[J]. J Heterocycl Chem, 2014,51(6):1689-1696. doi: 10.1002/jhet.1809
33. [33]
  Azarifar A, Nejat-Yami R, Azarifar D. Nano-ZnO:An Efficient and Reusable Catalyst for One-Pot Synthesis of 1H-pyrazolo[1, 2-b]phthalazine-5, 10-diones and Pyrazolo[1, 2-a] [1, 2, 4]triazole-1, 3-diones[J]. J Iran Chem Soc, 2013,10:297-306. doi: 10.1007/s13738-012-0159-3
34. [34]
  Nabid M R, Rezaei S J T, Ghahremanzadeh R. Ultrasound-Assisted One-Pot, Three-Component Synthesis of 1H-Pyrazolo[1, 2-b]phthalazine- 5, 10-Diones[J]. Ultrason Sonochem, 2010,17(1):159-161.
35. [35]
  Kefayati H, Delafrooz A, Homayoon S. Ultrasound-Assisted Synthesis of Pyrazolo[1, 2-b]phthalazines and Dihydrospiro[Indoline-3, 1'-Pyrazolo[1, 2-b]phthalazines] Using TBAF as an Efficient Phase-Transfer Catalyst[J]. Russ J Gen Chem, 2016,86(7):1735-1740. doi: 10.1134/S107036321607032X
36. [36]
  Lamera E, Bouacida S, Merazig H. DMAP as a New Efficient Catalyst for the One-Pot Synthesis of Condensed Phthalazines[J]. Z Naturforsch B, 2017,72(5):361-368. doi: 10.1515/znb-2016-0262
37. [37]
  Koyel P, Sanjay P, Asish R D. Synthesis of a Diversified Combinatorial Library of 1H-pyrazolo[1, 2-b]phthalazine-5, 10-dione Derivatives Applying Sustainable Carbon-based Solid Acid Catalyst Involving a Domino Four-component Reaction[J]. Monatsh Chem, 2014,145(8):1343-1352. doi: 10.1007/s00706-014-1195-8
38. [38]
  Franca B, Silvia C, Leonetto F. Clean Synthesis in Water.Part 2:Uncatalysed Condensation Reaction of Meldrum's Acid and Aldehydes[J]. Tetrahedron Lett, 2001,42(31):5203-5205. doi: 10.1016/S0040-4039(01)00978-9
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. [2]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
3. [3]
  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
4. [4]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
5. [5]
  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
6. [6]
  Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu₂O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-. doi: 10.3866/PKU.WHXB202407020
7. [7]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
8. [8]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
9. [9]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
10. [10]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
11. [11]
  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
12. [12]
  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
13. [13]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
14. [14]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
15. [15]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
16. [16]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
17. [17]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
18. [18]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
19. [19]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
20. [20]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(737)
HTML views(74)

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