One-Pot Synthesis of Substituted Phthalazine-5,10-dione Derivatives in the Presence of Triflate Catalyst

Abstract

In this study, substituted 1H-pyrazolo[1,2-b]phthalazine-5,10-diones which are considered that may possess biological activity have been obtained via one-pot multi-component cyclocondensation reaction of phthalhydrazide, aromatic aldehydes and malononitrile catalyzed in the presence of Cu(OTf)₂ in very good yields and short times. The structures of all these synthesized compounds (4a-f) have been determined and characterized by infrared, nuclear magnetic resonance, mass spectral data, and elemental analysis.

Keywords

• Phthalazinedione,triflate,one-pot,multicomponent,green chemistry

References

1. Abdesheikhi M, Karimi-Jaberi Z, 2015. Four-component synthesis of 3-amino-1-aryl-5,10-dioxo-1H-pyrazolo[1,2-b] phthalazine-2-carbonitrile derivatives promoted by potassium carbonate. Chemical Research, 39: 482–483.
2. Arora P, Rajput JK, 2017. Amelioration of H4[W12SiO40] by nanomagnetic heterogenization: For the synthesis of 1H–pyrazolo[1,2‐b]phthalazinedione derivatives. Apllied Organometallic Chemistry, 32: 1-18.
3. Bashti A, Kiasat AR, Mokhtari B, 2015. Synthesis and characterization of dicationic 4,4’-bipyridinium dichloride ordered mesoporous silica nanocomposite and its application in the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Royal Society of Chemistry Advances, 5: 25816-25823.
4. Dabholkar V, Badhe K, Kurade S, 2017. One-pot four component synthesis of 1H-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives using calcined Mg-Fe hydrotalcite catalyst. Internationl Journal of Current Advanced Research, 6:8416-8420.
5. Dabholkar V, Kurade S, Badhe K, 2018. Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using NiFe2O4 nanoparticle as a heterogeneous catalyst. Der Pharma Chemica, 10: 135-141.
6. Eswararao S, Venkataramireddy V, Sreenivasareddy M, Kumar P, 2017. Water mediated one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-triones, Heterocyclic Letters, 7(3): 895-903.
7. Ghahremanzadeh R, Shakibaei GI, Bazgir A, 2008. An efficient one-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Synlett, 8:1129-1132.
8. Ghomi JS, Alavi HS, Ziarati A, Teymuri R, Saberi MR, 2014. A highly flexible green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives with CuI nanoparticles as catalyst under solvent-free conditions. Chinese Chemical Letters, 25:401-405.

9. Ghorbani-Vaghei R, Noori S, Toghraei-Semiromi Z, Salimi Z, 2014. One-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solventfree conditions. Royal Chemical Society Advances 4: 47925–47928.
10. Ghorbani-Vaghei R, Mahmoodi J, Maghbooli Y, 2016. Preparation and characterization of nanomagnetic piperidinium benzene‐1,3‐disulfonate ionic liquid as a novel, green and heterogeneous catalyst and its use in the synthesis of 1H–pyrazolo[1,2‐b]phthalazine‐5,10‐diones and 1H–pyrazolo[1,2‐a]pyridazine‐5,8‐diones under solvent‐free conditions, Apllied Organometallic Chemistry, 31: 1-10.
11. Hosseininasab N, Davoodnia A, Rostami-Charati F, Khojastehnezhad A, 2017. Preparation, characterization, and first catalytic application of a novel phosphotungstic acid-containing ionic liquid immobilized on CuFe2O4@SiO2 magnetic nanoparticles in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Russian Journal of General Chemistry, 87(10): 2436–2443.
12. Kefayati H, Amlashi SH, Kazemi-Rad R, Delafrooz A. 2014. Electrocatalytic multicomponent assembling of phthalhydrazide, aldehydes and malononitrile: An efficient approach to 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Comptes Rendus Chimie. 17: 894-898.
13. Kefayati H, Delafrooz A, Homayoon S, 2016. 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. Russian Journal of General Chemistry, 86(7): 1735–1740.
14. Kiasat AR and Davarpanah J, 2013. Fe3O4@silica sulfuric acid nanoparticles: An efficient reusable nanomagnetic catalyst as potent solid acid for one-pot solvent-free synthesis of indazolo[2,1-b] phthalazine-triones and pyrazolo[1,2-b]phthalazine-diones. Journal of Molecular Catalysis A: Chemical, 373: 46-54.
15. Kobayashi S, Sugiura M, Kitagawa H, Lam WWL, 2002. Rare-earth metal triflates in organic synthesis, Chemical Reviews, 102(6): 2227-2302.
16. Lamera E, Bouacida S, Merazig H, Chibani A, Le Borgne M, Bouaziz Z, Bouraiou A, 2017. DMAP as a new efficient catalyst for the one-pot synthesis of condensed phthalazines. Zeitschrift für Naturforschung B, 72:361-368.
17. Lv PC, Sun J, Luo Y, Yang Y, Zhu HL, 2010. Design, synthesis, and structure–activity relationships of pyrazole derivatives as potential FabH inhibitors. Bioorganic & Medicinal Chemistry, 20: 4657-4660.
18. Mohamadpour F, Maghsoodlou MT, Heydari R, 2016. Mojtaba Lashkari2Saccharin: a green, economical and efficient catalyst for the one‑pot, multi‑component synthesis of 3,4‑dihydropyrimidin‑2‑(1H)‑one derivatives and 1H‑pyrazolo[1,2‑b]phthalazine‑5,10‑dione derivatives and substituted dihydro‑2‑oxypyrrole. Journal of the Iranian Chemical Society, 13:1549-1560.
19. Mohamadpour F, Lashkari M, Heydari R, Hazeri N, 2018. Four-component clean process for the eco-friendly synthesis of 1H-pyrazolo [1,2-b]phthalazine-5,10-dione derivatives using Zn(OAc)2.2H2O as an efficient catalyst under solvent-free conditions. Indian Journal of Chemistry, 57B:843-851.
20. Nabid MR, Rezaei SJT, Ghahremanzadeh R, Bazgir A, 2010. Ultrasound-assisted one-pot, three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Ultrasonics Sonochemistry, 17: 159-161.
21. Piltan M, 2017. Preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones using ZrO2 nanoparticles as a catalyst under solvent-free conditions. Heterocyclic Communications, 23:401-403.
22. Raghuvanshi DS and Singh KN, 2011. A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies. Tetrahedron Letters, 52: 5702-5705.
23. Reddy MV and , Jeong YT, 2013. InCl3-catalyzed green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones under solvent-free conditions. Tetrahedron Letters, 2013, 54(27): 3546-3549.
24. Reddy MV, Kumar PCR, Reddy GCS, Reddy CS, 2014. Silica gel-supported tungstic acid (STA): A new, highly efficient and recyclable catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione carbonitriles and carboxylates under neat conditions. Comptes Rendus Chimie, 17:1250-1256.
25. Roy HN, Rana M, Al Munsur AZ, Lee K, Sarker AK, 2016. An efficient and convenient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives mediated by L-proline. Synthethic Communications, 46:1370-1376.
26. Sabour FH, Nasr‑Esfahani M, Mohammadpoor‑Baltork I, Tangestaninejad S, Moghadam M, Mirkhani V, 2018. 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. Journal of the Iranian Chemical Society, 15:671–683.
27. Sangani CB, Makwana JA, Duan YT, Thumar NJ, Zhao MY, Patel YS, Zhu HL, 2016. Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: Assessment of their antimicrobial, antituberculosis and antioxidant activity. Research on Chemical Intermediates, 42:2101-2117.
28. Shah NM, Patel MP, Patel RG, 2012. An efficient and facile synthesis of 1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐dione derivatives of biological interest. Heterocyclic Chemistry, 49:1310-1316.
29. Shaikh MA, Farooqui M, Abed S, 2018. [Bu3NH][HSO4] catalyzed: an eco-efficient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 2H-indazolo[2,1-b]phthalazine-triones under solvent-free conditions. Research on Chemical Intermediates, 44: 5483–5500.
30. Shaterian HR, Mohammadnia M, 2012. Mild basic ionic liquids catalyzed new four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones, Journal of Molecular Liquids, 173:55-61.
31. Song SH, Zhong J, He YH, Guan Z, 2012. One-pot four-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Tetrahedron Letters, 53:7075-7077.
32. Tayade YA, Dalal DS, 2017. β-Cyclodextrin as a supramolecular catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives in water. Catalysis Letters, 147:1411-1421.
33. Teimouri MB, 2006. One-pot three-component reaction of isocyanides, dialkyl acetylenedicarboxylates and phthalhydrazide: synthesis of highly functionalized 1H-pyrazolo[1,2-b]phthalazine-5,10-diones. Tetrahedron, 62:10849-10853.
34. Torkiana L, Dabiri M, Salehi P, Bararjaniana M, 2011. An efficient one-pot, four-component synthesis of {[(1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Helvetica Chimica Acta, 94: 1416-1425.
35. Vafaee A, Davoodnia A, Pordel M, Bozorgmehr MR, 2015. 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. Oriental Journal of Chemistry, 31:2153-2158.
36. Vaghei RG, Noori S, Semiromi ZT, Salimi Z, 2014. One-pot synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under solvent-free conditions. Royal Society of Chemistry Advances, 4:47925-47928.
37. Vera-DiVaio MAF, Freitas ACC, Castro HC, de Albuquerque S, Cabral LM, Rodrigues CR, Albuquerque MG, Martins RCA, Henriques MGMO, Dias LRS, 2009. Synthesis, antichagasic in vitro evaluation, cytotoxicity assays, molecular modeling and SAR/QSAR studies of a 2-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)-acrylic acid benzylidene-carbohydrazide series. Bioorganic & Medicinal Chemistry, 17: 295–302.
38. Wang W, Cong-Hao L, Yi Y, Xiao-Jun L, Hong-Yun G, 2016. An improved procedure for the three-component synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives using basic ionic liquid. Journal of Chemical Research, 40: 354-357.
39. Wei F, Zhao BX, Huang B, Zhang L, Sun CH, Dong WL, Shin DS, Miao JY, 2006. Design, synthesis, and preliminary biological evaluation of novel ethyl 1-(2'-hydroxy-3'-aroxypropyl)-3-aryl-1H-pyrazole-5-carboxylate. Bioorganic & Medicinal Chemistry Letters, 16: 6342-6347.
40. Wender PA, Handy ST, Wright DL, 1997. Towards the ideal synthesis. Chemistry and Industry. 19: 765-768.
41. Xia Y, Dong ZW, Zhao BX, Ge X, Meng N, Shin DS, Miao JY, 2007. Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide derivatives as potential agents against A549 lung cancer cells. Bioorganic & Medicinal Chemistry, 15: 6893–6899.
42. Zhang S, Zhao Y, Liu Y, Chen D, Lan W, Zhao Q, 2010. Synthesis and antitumor activities of novel 1,4-disubstituted phthalazine derivatives. European Journal of Medicinal Chemistry, 45(8): 3504-3510.