journal article·2014-05

Nanocrystalline magnesium oxide: an efficient promoter and heterogeneous nano catalyst for the one-pot synthesis of pyrazolotriazoles in green medium

Hossein Naeimi, Zahra Rashid, Amir-Hassan Zarnani, Ramin Ghahremanzadeh

Journal of Nanoparticle Research· Volume 16· Issue 5
Publisher page

Abstract

A simple, efficient, and relatively clean method for the synthesis of pyrazolo[1,2-a][1,2,4]triazole derivatives via a one-pot three-component reaction of aromatic aldehydes, 4-phenyl-1,2,4-triazolidine-3,5-dione, and malononitrile or alkyl cyanoacetates in the presence of a catalytic amount of nanocrystalline (NC) magnesium oxide has been developed. This method has several advantages such as, high to excellent product yields, reusability of catalyst, and simple work-up procedure in the nontoxic medium.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Multicomponent Synthesis of Heterocycles · Microwave-Assisted Synthesis and Applications · Synthesis and biological activity

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References (60)

Show source-provided references
1. Abdel-Aziz M, Abuo-Rahma GA, Hassan AA (2009) Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Med Chem 44:3480–348710.1016/j.ejmech.2009.01.032 ↗
2. Abonia R, Castillo J, Insuasty B, Quiroga J, Nogueras M, Cobo J (2013) Efficient catalyst-free four-component synthesis of novel γ-aminoethers mediated by a Mannich type reaction. ACS Comb Sci 15:2–910.1021/co300105t ↗
3. Alonso F, Moglie Y, Radivoy G, Yus M (2011) Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon. Org Biomol Chem 9:6385–639510.1039/c1ob05735a ↗
4. Balbi A, Anzaldi M, Maccio C, Aiello C, Mazzei M, Gangemi R, Castagnola P, Miele M, Rosano C, Viale M (2011) Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity. Eur J Med Chem 46:5293–530910.1016/j.ejmech.2011.08.014 ↗
5. Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P (2010) Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,40-pyrazolo[3,4-b] pyridine]-2,60(10H)-diones in water. Ultrason Sonochem 17:447–45210.1016/j.ultsonch.2009.09.009 ↗
6. Bazgir A, Hosseini G, Ghahremanzadeh R (2013) Copper ferrite nanoparticles: an efficient and reusable nanocatalyst for a green one-pot, three-component synthesis of spirooxindoles in water. ACS Comb Sci 15:530–53410.1021/co400057h ↗
7. Berłożecki S, Szymanski W, Ostaszewski R (2008) α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield and stereoselectivity. Tetrahedron 64:9780–978310.1016/j.tet.2008.07.064 ↗
8. Bose AK, Pednekar S, Ganguly SN, Chakraborty G, Manhas MS (2004) A simplified green chemistry approach to the Biginelli reaction using ‘Grindstone Chemistry’. Tetrahedron Lett 45:8351–835310.1016/j.tetlet.2004.09.064 ↗
9. Bretherick L (1994) Hazards in the chemical laboratory, 6th edn. Royal Society of Chemistry, Cambridge
10. Chaim R, Shen ZJ, Nygren M (2004) Transparent nanocrystalline MgO by rapid and low-temperature spark plasma sintering. J Mater Res 19:2527–253110.1557/JMR.2004.0334 ↗
11. Chen D, Jordan EH, Gell M (2008) Pressureless sintering of translucent MgO ceramics. Scr Mater 59:757–75910.1016/j.scriptamat.2008.06.007 ↗
12. Cheng Ch, Jiang B, Tu Sh, Li G (2011) [4+2+1] Domino cyclization in water for chemo- and regioselective synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine derivatives. Green Chem 13:2107–211510.1039/c1gc15183e ↗
13. Choudary BM, Mahendar K, Ranganath KVS (2005a) Wadsworth–Emmons reactions catalyzed by nanocrystalline MgO. J Mol Catal A 234:25–2710.1016/j.molcata.2005.02.019 ↗
14. Choudary B, Ranganath KVS, Pal U, Kantam ML, Sreedhar B (2005b) Nanocrystalline MgO for asymmetric Henry and Michael reactions. J Am Chem Soc 127:13167–1317110.1021/ja0440248 ↗
15. Choudary BM, Ranganath KVS, Yadav J, Lakshmi Kantam M (2005c) Synthesis of flavanones using nanocrystalline MgO. Tetrahedron Lett 46:1369–137110.1016/j.tetlet.2004.12.078 ↗
16. Choudary BM, Chakrapani LT, Kumar KVR, Kantum ML (2006) Direct asymmetric aldol reaction catalyzed by nanocrystalline magnesium oxide. Tetrahedron 62:9571–957610.1016/j.tet.2006.07.091 ↗
17. Dick FD (2006) Solvent neurotoxicity. Occup Environ Med 63:221–22610.1136/oem.2005.022400 ↗
18. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168–321010.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U ↗
19. El-Moghazy SM, Barsoum FF, Abdel-Rahman HM, Marzouk AA (2012) Synthesis and anti-inflammatory activity of some pyrazole derivatives. Med Chem Res 21:1722–173310.1007/s00044-011-9691-4 ↗
20. Faghihi-Sani MA, Yamaguchi A (2002) Oxidation kinetics of MgO–C refractory bricks. Ceram Int 28:835–83910.1016/S0272-8842(02)00049-4 ↗
21. Fu L, Shi Q, Shi Y, Jiang B, Tu Sh (2013) Three-component domino reactions for regioselective formation of bis-indole derivatives. ACS Comb Sci 15:135–14010.1021/co3001428 ↗
22. Ganguly A, Trinh P, Ramanujachary KV, Ahmad T, Ganguli AMA (2011) Reverse micellar based synthesis of ultrafine MgO nanoparticles (8–10 nm): characterization and catalytic properties. J Colloid Interface Sci 353:137–14210.1016/j.jcis.2010.09.041 ↗
23. Ghahremanzadeh R, Ahadi S, Sayyafi M, Bazgir A (2008) Reaction of phthalhydrazide and acetylenedicarboxylates in the presence of N-heterocycles: an efficient synthesis of phthalazine derivatives. Tetrahedron Lett 49:4479–448210.1016/j.tetlet.2008.05.063 ↗
24. Ghahremanzadeh R, Amanpour T, Sayyafi M, Bazgir A (2010) One-pot three-component synthesis of spironaphthopyrano[2,3-d]pyrimidine-5,3’-indolines in water. J Heterocyclic Chem 47:421–42410.1002/jhet.331 ↗
25. Guo Q, Cong-Gui Zhao J, Arman H (2012) Base-catalyzed three-component direct Mannich reaction of enolizable ketones with high syn-selectivities. Tetrahedron Lett 53:4866–486910.1016/j.tetlet.2012.06.140 ↗
26. Haddad N, Salvango A, Busacca C (2004) Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles. Tetrahedron Lett 45:5935–593710.1016/j.tetlet.2004.05.038 ↗
27. Hailes HC (2007) Reaction solvent selection: the potential of water as a solvent for organic transformations. Org Process Res Dev 11:114–12010.1021/op060157x ↗
28. Hasaninejad A, Zare A, Shekouhy M (2011) Highly efficient synthesis of triazolo[1,2-a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent-free conditions. Tetrahedron 67:390–40010.1016/j.tet.2010.11.029 ↗
29. Hasaninejed A, Rasekhi Kazerooni M, Zare A (2012) Solvent-free, one-pot, four-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones using sulfuric acid-modified PEG-6000 as a green recyclable and biodegradable polymeric catalyst. Catal Today 196:148–15310.1016/j.cattod.2012.05.026 ↗
30. Herrera M, Knepper I, Souza N, Villinger A, Sosnovskikh V, Iaroshenko V (2012) One-pot, three-component synthesis of 7-azaindole derivatives from N-substituted 2-amino-4-cyanopyrroles, various aldehydes, and active methylene compounds. ACS Comb Sci 14:434–44110.1021/co300042v ↗
31. Hutchinson TH, Shillabeer N, Winter MJ, Pickford DB (2006) Acute and chronic effects of carrier solvents in aquatic organisms: a critical review. Aquat Toxicol 76:69–9210.1016/j.aquatox.2005.09.008 ↗
32. Jain D, Rani A (2011) VII—proceedings, March 6th, 1879 additions to the library of the American Chemical Society, from Jan. 1, to March 1, 1879 list of exchanges received during January and February, 1879. J Am Chem Sci 1:37–4310.9734/ACSJ/2011/335 ↗
33. Jeevanandam P, Klabunde KJ (2002) A study on adsorption of surfactant molecules on magnesium oxide nanocrystals prepared by an aerogel route. Langmuir 18:5309–531310.1021/la0200921 ↗
34. Kantam ML, Ranganath KVS, Mahendar K, Chakrapani L, Choudary BM (2007a) Asymmetric Michael addition of malonates to enones catalyzed by nanocrystalline MgO. Tetrahedron Lett 48:7646–764910.1016/j.tetlet.2007.08.108 ↗
35. Kantam ML, Pal U, Sreedhar B, Choudary BM (2007b) An efficient synthesis of organic carbonates using nanocrystalline magnesium oxide. Adv Synth Catal 349:1671–167510.1002/adsc.200600525 ↗
36. Karmakar B, Banerji J (2011) A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction. Tetrahedron Lett 52:4957–496010.1016/j.tetlet.2011.07.075 ↗
37. Lin R, Connolly PJ, Lu Y, Chiu G, Li S, Yu Y, Huang S, Li X, Emanuel SL, Middleton SA, Gruninger RH, Adams M, Fuentes-Pesquera AR, Greenberger LM (2007) Synthesis and evaluation of pyrazolo[3,4-b]pyridine CDK1 inhibitors as anti-tumor agents. Bioorg Med Chem Lett 17:4297–430210.1016/j.bmcl.2007.05.029 ↗
38. Marcaccini S, Menchi G, Trabocchi A (2011) Synthesis of diverse phenylglycine derivatives via transformation of Ugi four-component condensation primary adducts. Tetrahedron Lett 52:2673–267510.1016/j.tetlet.2011.03.074 ↗
39. Meshkani F, Rezaei M (2009) Facile synthesis of nanocrystalline magnesium oxide with high surface area. Powder Technol 196:85–8810.1016/j.powtec.2009.07.010 ↗
40. Moshtaghi Zonouz A, Eskandari I, Khavasi HR (2012) 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. Tetrahedron Lett 53:5519–552210.1016/j.tetlet.2012.08.010 ↗
41. Naeimi H, Rashid R, Zarnani AH, Ghahremanzadeh R (2014) Efficient synthesis of novel spiro-furo-pyridopyrimidine-indolines by manganese ferrite nanoparticles as a highly active magnetically reusable nanocatalyst in water. New J Chem 38:348–35710.1039/C3NJ00940H ↗
42. Parameswaran PS, Naik CG, Hegde VR (1997) Secondary metabolites from the sponge Tedania anhelans: isolation and characterization of two novel pyrazole acids and other metabolites. J Nat Prod 60:802–80310.1021/np970134z ↗
43. Pipitone DA (2004) Safe storage of laboratory chemicals, 2nd edn. Wiley-Interscience, New York
44. Prakash O, Kumar R, Parkash V (2008) Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromones. Eur J Med Chem 43:435–44010.1016/j.ejmech.2007.04.004 ↗
45. Reddy M, Ashoka S, Chandrappa G, Pasha M (2010) Nano-MgO: an efficient catalyst for the synthesis of formamides from amines and formic acid under MWI. Catal Lett 138:82–8710.1007/s10562-010-0372-6 ↗
46. Richards R, Li W, Decker S, Davidson C, Koper O, Zaikovski V, Volodin A, Rieker T, Klabunde KJ (2000) Consolidation of metal oxide nanocrystals. Reactive pellets with controllable pore structure that represent a new family of porous, inorganic materials. J Am Chem Soc 122:4921–492510.1021/ja994383g ↗
47. Rondot R, Zhu J (2005) Synthesis of chiral vicinal diamines by highly diastereoselective three-component phenolic Mannich reaction: temperature-dependent stereodivergency. Org Lett 7:1641–164410.1021/ol050334z ↗
48. Ross GF, Herdtweck E, Ugi I (2002) Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-d-xylopyranose—an effective and selectively removable chiral auxiliary. Tetrahedron 58:6127–613310.1016/S0040-4020(02)00484-2 ↗
49. Saha B, Frett B, Wang Y, Li H (2013) A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines. Tetrahedron Lett 54:2340–234310.1016/j.tetlet.2013.02.055 ↗
50. Simon M, Li C (2012) Green chemistry oriented organic synthesis in water. Chem Soc Rev 41:1415–142710.1039/C1CS15222J ↗
51. Sridhar R, Paramasivam TP, Sundaresan E, Guruswamy S, Mondikalipudur NP, Vaiyapuri RP, Mathivanan N (2004) Design, synthesis and anti-microbial activity of 1H-pyrazole carboxylates. Bioorg Med Chem Lett 14:603510.1016/j.bmcl.2004.09.066 ↗
52. Steiner B, Langer V, Bella M, Koos M (2013) Cyanohydrins from methyl 6-deoxy-2,3-O-isopropylidene-α-l-lyxo-hexofuranosid-4-ulose via Bucherer-Bergs and Strecker reactions. Carbohydr Res 369:31–3710.1016/j.carres.2012.09.008 ↗
53. Tucker TJ, Sisko JT, Tynebor RM, Williams TM, Felock PJ, Flynn AJ, Lai MT, Liang Y, McGaughey G, Liu M, Miller M, Moyer G, Munshi V, Perlow-Poehnelt R, Prasad S, Reid JC, Sanchez R, Torrent M, Vacca JP, Wan BL, Yan Y (2008) Discovery of 3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridine-3-yl)methoxy]-2-chlorophenoxy}-5 chlorobenzonitrile (MK-4965): a potent, orally bioavailable HIV-1 non-nucleoside reverse transcriptase inhibitor with improved potency against key mutant viruses. J Med Chem 51:6503–651110.1021/jm800856c ↗
54. Ugi I, Werner B, Dömling A (2003) The chemistry of isocyanides, their multicomponent reactions and their libraries. Molecules 8:53–6610.3390/80100053 ↗
55. Upadhyay K, Bavishi A, Thakrar S, Radadiya A, Vala H, Parekh S, Bhavsar D, Savant M, Parmar M, Adlakha P, Shah A (2011) Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity. Bioorg Med Chem Lett 21:2547–254910.1016/j.bmcl.2011.02.016 ↗
56. Utamapanya S, Klabunde KJ, Schlup JR (1991) Nanoscale metal oxide particles/clusters as chemical reagents. Synthesis and properties of ultrahigh surface area magnesium hydroxide and magnesium oxide. Chem Mater 3:175–18110.1021/cm00013a036 ↗
57. Valavanidis A (1996) Research staff in chemical, biomedical laboratories. Risk assessment of various occupational diseases and occupational cancer. Arch Greek Med 13(6):488–503
58. Wang H, Shi D (2013) Efficient synthesis of functionalized dihydro-1H-indol-4(5H)-ones via one-pot three-component reaction under catalyst-free conditions. ACS Comb Sci 15:261–26610.1021/co4000198 ↗
59. Wang Sh, Cheng Ch, Wu F, Jiang B, Shi F, Tu S, Rajale T, Li G (2011) Microwave-assisted multi-component reaction in water leading to highly regioselective formation of benzo[f] azulen-1-ones. Tetrahedron 67:4485–449310.1016/j.tet.2011.05.002 ↗
60. Xiao Zh, Lei M, Hu L (2011) An unexpected multi-component reaction to synthesis of 3-(5-amino-3-methyl-1H-pyrazol-4-yl)-3-arylpropanoic acids in ionic liquid. Tetrahedron Lett 52:7099–710210.1016/j.tetlet.2011.10.099 ↗