Synthesis of Pyridazine Derivatives by Base-Catalyzed Three-Component Reaction of Aldehyde, Malononitrile and Phthalhydrazide
- Corresponding author: LÜ Chengwei, chengweilv@126.com
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
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
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
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
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.
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
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
Franklin E C. Heterocyclic Nitrogen Compounds.I.Pentacyclic Compounds[J]. Chem Rev, 1935,16(3):305-361. doi: 10.1021/cr60055a001
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
Lichtenthaler F W. Unsaturated O- and N-heterocycles from Carbohydrate Feedstocks[J]. Acc Chem Res, 2002,35(9):728-737. doi: 10.1021/ar010071i
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
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.
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
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
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
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
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.
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
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
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.
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
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
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
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.
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
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
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
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.
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.
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
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.
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
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
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
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.
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
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
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
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
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