CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity

Yıl: 2017 Cilt: 4 Sayı: 2 Sayfa Aralığı: 631 - 647 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022

CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity

Öz:
New fused pyrazolo[4,3-e]pyridines were obtained by three-component reaction of 1,3-dimethyl-1H-pyrazol-5-amine or 3-phenyl-1H-pyrazol-5-amine, aromatic aldehydes and indan-1,3-dione in the presence of camphor-10-sulfonic acid (CSA) as an effective catalyst under ultrasound promoted conditions. The antioxidant activity of the pyrazolopyridine compounds 4b, 5c, 5e, 7a, 7b and 7c were determined
Anahtar Kelime:

Konular: Mühendislik, Kimya
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • 1. Dömling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Reviews. 2006; 106: 17-89. DOI: 10.1021/cr0505728.
  • 2. Zhu J, Bienayme H. Eds. Multicomponent Reactions, Wiley-VCH: Weinheim, 2005, 484 p. ISBN: 978-3-527-30806-4.
  • 3. Sunderhaus J.D, Martin S.F. Application of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chemistry-A European Journal. 2009; 15: 1300-08. DOI: 10.1002/chem.200802140.
  • 4. Dömling A, Ugi I. Multicomponent reactions with isocyanides. Angewandte Chemie International Edition. 2000; 39: 3168-3210. DOI: 10.1002./1521- 3773(20000915)39:18<3168AID-ANIE3168>3.0CO;2-U.
  • 5. Zhu J, Wang Q, Wang M. X, Eds.; Multicomponent Reactions in Organic Synthesis, WileyVCH: Weinheim, 2015, 521 p. ISBN: 978-3-527-33237-3.
  • 6. Crenshaw R. R, Luke G. M, Smirnoff P. Interferon inducing activities of derivatives of 1,3- dimethyl-4-(3-dimethylaminopropylamino)-1H-pyrazolo[3,4-b]quinoline and related compounds. J. Med. Chem. 1976; 19: 262-275. DOI: 10.1021/jm00224a013
  • 7. Crenshaw R, Luke G. M, Smirnoff P. Canadian Patent 10, 32, 538; Chem. Abstr. 89 (1978) 179995r.
  • 8. Huang S, Lin R, Yu Y, Lu Y, Connolly P.J, Chiu G, Li S, Emanuel S.L, Middleton S.A. Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor. Bioorg. Med. Chem. Lett. 2007; 17: 1243-45. DOI: 10.1016/j.bmcl.2006.12.031.
  • 9. Saggar S.A, Sisko J.T, Tucker T.J, Tynebor R.M, Su D.S, Antony N.J. US 2007021442, 2007.
  • 10. Zhang P, Pennell A.M.K, Wright J.J.K, Chen W, Leleti M. R, Li Y, Li L, Xu Y. WO 2007002293, 2007 [Chem. Abstr. 2007, 146, 121980].
  • 11. Chiu G, Li S, Connolly P.J, Middleton S.A, Emanuel S.L, Huang R, Lu Y. WO 2006130673, 2006 [Chem. Abstr. 2006, 146, 45513].
  • 12. Feurer A, Luithle J, Wirtz S, Koenig G, Stasch J, Stahl E, Schreiber R, Wunder F, Lang D. WO 2004009589, 2004 [Chem. Abstr. 2004, 140, 146157].
  • 13. Bristol-Meyers Co., French Demande 2, 149, 275; Chem. Abstr. 79 (1973) 78784n.
  • 14. Stein R.G, Biel J.H, Singh T. Antimalarials. 4-Substituted 1H-pyrazolo[3,4-b]quinolines. J. Med. Chem. 1970; 13: 153-55. DOI: 10.1021/jm00295a049.
  • 15. Kendre D.B, Toche R.B, Jachak M.N. Synthesis of novel dipyrazolo[3,4-b:3,4-d]pyridines and study of their fluorescence behavior. Tetrahedron. 2007; 63: 11000-04. DOI: 10.1016/j.tet.2007.08.052.
  • 16. Diaz-Ortiz A, Dela Hoz A, Langa F. Microwave irradiation in solvent-free conditions: a ecofriendly methodology to prepare indazoles, pyrazolopyridines and bipyrazoles by cycloaddition reactions. Green Chem. 2000; 2: 165-72. DOI: 10.1039/B003752O.
  • 17. Krygowski T.M, Anulewicz R, Cyranski M.K, Puchala A, Rasala D. Seperation of the energetic and geometric contribution to the aromaticity. Part IX. Aromaticity of pyrazoles in dependence on the kind of substitution. Tetrahedron. 1998; 54: 12295-300. DOI: 10.1016/S0040-4020(98)00749-2.
  • 18. Nikpassand M, Mamaghani M, Shirini F, Tabatabaeian K. A convenient ultrasound-promoted regioselective synthesis of fused polycyclic 4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4- b]pyridines. Ultrasonics Sonochemistry. 2010; 17: 301-5. DOI:10.1016/j.ultsonch.2009.08.001.
  • 19. Nikpassand M, Zare L, Shafaati T, Shariati S. Regioselective synthesis of fused azo-linked pyrazolo[4,3-e]pyridines using nano-Fe3O4. Chin. J. Chem. 2012; 30: 604-8. DOI: 10.1002/cjoc.201100181.
  • 20. Kundu K, Nayak S.K. (±)-Camphor-10-sulfonic acid catalyzed direct one-pot threecomponent Mannich type reaction of alkyl (hetero)aryl ketones under solvent-free conditions: application to the synthesis of aminochromans. RSC Advances. 2012; 2012: 480-6. DOI: 10.1039/C1RA00652E.
  • 21. Srivastava A, Singh S, Samanta S. (±)-CSA catalyzed Friedel–Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3- indolylisoindolin-1-ones bearing a quaternary a-amino acid moiety. Tetrahedron Letters. 2013; 54: 1444-8. DOI: 10.1016/j.tetlet.2013.01.010
  • 22. Jiang X, Song Z, Xu C, Yao Q, Zhang A. (D,L)-10-Camphorsulfonic-acid-catalysed synthesis of diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes from 2-hydroxychalcones and naphthol derivatives. European Journal of Organic Chemistry. 2014; 418-25. DOI: 10.1002/ejoc.201301295.
  • 23. Srivastava A, Mobin S.M, Samanta S. (±)-CSA catalyzed one-pot synthesis of 6,7- dihydrospiro[indole-3,10-isoindoline]-2,30,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids. Tetrahedron Letters. 2014; 55: 1863-7. DOI: 10.1016/j.tetlet.2014.01.154.
  • 24. Dai W.M, Wu J, Fong K.C, Lee M.Y.H, Lau C.W. Regioselective synthesis of acyclic cisenediynes via an acid-catalyzed rearrangement of 1,2-dialkynylallyl alcohols. Syntheses, computational calculations, and mechanism. Journal of Organic Chemistry. 1999; 64: 5062-82. DOI: 10.1021/jo982476v.
  • 25. Kellogg R.M, Nieuwenhuijzen J.W, Pouwer K, Vries T.R, Broxterman Q.B, Grimbergen R.F.P, Kaptein B, La Crois R.M, De Wever E, Zwaagstra K, Van Der Laan A.C. Dutch resolution: Separation of enantiomers with families of resolving agents. A status report. Synthesis. 2003; 1626-38. DOI: 10.1055/s-2003-40508.
  • 26. Vinatoru M, Bartha E, Badea F, Luche J.L. Sonochemical and thermal redox reactions of triphenylmethane and triphenylmethyl carbinol in nitrobenzene. Ultrasonics Sonochemistry. 1998; 5: 27-31. DOI: 10.1016/S1350-4177(98)00004-2.
  • 27. Pelit E, Turgut Z. Three-component aza-Diels–Alder reactions using Yb(OTf)3 catalyst under conventional/ultrasonic techniques. Ultrasonics Sonohemistry. 2014; 21: 1600-7. DOI: 10.1016/j.ultsonch.2014.01.009.
  • 28. Dong C, Sanjay K, Ackmez M. Eds. Handbook on Applications of Ultrasound Sonochemistry for Sustainability. Boca Raton: CRC Press, Taylor & Francis Group; 2012, 793 p. ISBN: 9781439842065-CAT#K11960.
  • 29. Mason T.J, Peters D. Eds. Practical Sonochemistry, second ed., Power ultrasound uses and applications. Woodhead Publishing, 2002, 166p. ISBN: 9781898563839.
  • 30. Mason T.J. Sonochemistry and the environment – Providing a ‘‘green’’ link between chemistry, physics and engineering. Ultrasonics Sonochemistry. 2007; 14: 476-83. DOI: 10.1016/j.ultsonch.2006.10.008.
  • 31. Luche J.L. Ed. Synthetic Organic Sonochemistry, Plenium Press, New York, 1998, 431 p. ISBN: 978-1-4899-1912-0.
  • 32. Li J.T, Wang S.X, Chen G.F, Li T.S. Some applications of ultrasound irradiation in organic synthesis. Current Organic Synthesis. 2005; 2: 415-36. DOI: 10.2174/1570179054368509.
  • 33. Sies H. Oxidative stres: oxidants and antioxidants. Experimental Physiology 1997; 82: 291- 5. DOI: 10.1113/expphysiol.1997.sp004024.
  • 34. Nakabeppu Y, Sakumi K, Sakamoto K, Tsuchimoto D, Tsuzuki T, Nakatsu Y. Mutagenesis and carsinogenesis caused by the oxidation of nucleic acdis. Biological Chemistry. 2006; 387: 373-9. DOI: 10.1515/BC.2006.050.
  • 35. Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT—Food Science and Technology. 1995; 28: 25–30. DOI: 10.1016/S0023-6438(95)80008-5.
  • 36. Oyaizu M. Studies on product of browning reaction prepared from glucose amine. Japanese Journal of Nutrition. 1986; 44: 307–15. DOI: 10.5264/eiyogakuzashi.44.307.
  • 37. Decker EA, Welch B. Role of ferritin as a lipid oxidation catalyst in muscle food. Journal of Agricultural and Food Chemistry. 1990; 38: 674–7. DOI: 10.1021/jf00093a019.
  • 38. Liu F, Ooi VEC, Chang ST. Free radical scavenging activity of mushroom polysaccharide extracts. Life Science. 1997; 60: 763-71. DOI: 10.1016/S0024-3205(97)00004-0.
  • 39. Mitsuda H, Yuasumoto K, Iwama K. Antioxidative action of indole compounds during the autooxidation of linoleic acid. J.Japan Soc. Nutr. Food Sci. 1996; 19: 210-14. DOI: 10.4327/jsnfs1949.19.210.
  • 40. Huang D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J. Agric. Food Chem. 2005; 53: 1841-56. DOI: 10.1021/jf030723c.
APA PELİT E (2017). CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. , 631 - 647.
Chicago PELİT Emel CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. (2017): 631 - 647.
MLA PELİT Emel CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. , 2017, ss.631 - 647.
AMA PELİT E CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. . 2017; 631 - 647.
Vancouver PELİT E CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. . 2017; 631 - 647.
IEEE PELİT E "CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity." , ss.631 - 647, 2017.
ISNAD PELİT, Emel. "CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity". (2017), 631-647.
APA PELİT E (2017). CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. Journal of the Turkish Chemical Society, Section A: Chemistry, 4(2), 631 - 647.
Chicago PELİT Emel CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. Journal of the Turkish Chemical Society, Section A: Chemistry 4, no.2 (2017): 631 - 647.
MLA PELİT Emel CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. Journal of the Turkish Chemical Society, Section A: Chemistry, vol.4, no.2, 2017, ss.631 - 647.
AMA PELİT E CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. Journal of the Turkish Chemical Society, Section A: Chemistry. 2017; 4(2): 631 - 647.
Vancouver PELİT E CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity. Journal of the Turkish Chemical Society, Section A: Chemistry. 2017; 4(2): 631 - 647.
IEEE PELİT E "CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity." Journal of the Turkish Chemical Society, Section A: Chemistry, 4, ss.631 - 647, 2017.
ISNAD PELİT, Emel. "CSA-Catalyzed Three-component Synthesis of Fused Polycyclic Pyrazolo[4,3-e]pyridines Under Ultrasonic Irradiation and Their Antioxidant Activity". Journal of the Turkish Chemical Society, Section A: Chemistry 4/2 (2017), 631-647.