Sonochemical hot-spot assisted one-pot synthesis of 4-arylmethylidene-2- phenyl-4H-oxazol-5-ones using nano-mgo as an efficient catalyst

Letters in Organic Chemistry

Volumn 10, Issue 4, 2013, Pages 283-290

  Saleh Azzam, Sadeq Hamood ^a   Chandrappa, G T ^a   Pasha, Mohamed Afzal ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

4 Arylmethylidene 2 phenyl 4H oxazol 5 ones; Acetic anhydride; Aromatic aldehydes; Hippuric acid; Nano MgO; Ultrasonic irradiation

Indexed keywords

EID: 84879778956     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178611310040010     Document Type: Article

References (50)

1. Ashraf, A. A. New cycloaddition reaction between 4-arylidene-2-phenyl- 5(4H)-1, 3-oxazolones and benzyne; facile synthesis of 1, 4(H)-benzoxazepine-2- ones and their N-phenyl derivatives, Tetrahedron, 2003, 59, 6067.
2. Tandel, C. R.; Manmen, D. Synthesis and study of some com-pounds containing oxazolone ring, sowing biological activity. Ind. J. Chem., 2008, 47B, 932.
3. Moxley, R. T,.; Ashwal, S.; McDonald, C.; Pandya, S.; Connolly, A.; Wade, C. Practice Parameter: Corticosteroid Treatment of Duchenne Dystrophy. Neurology, 2005, 64, 13.
4. Lesieur, A. H. Eur Pat, 1990, 390, 673
5. Chem. Abstr., (1991) 114:143.
6. Benedlt, D.; Daniel, V. Synthesis of 2-methyl-(Z)-4-(phenylimino) naphth[2, 3-d]oxazol-9-one, a monoimine quinone with selective cytotoxicity toward cancer cells. J. Med. Chem., 1994, 37, 710.
7. Pereira, E. R.; Sancelma, M.; Voldoire, A.; Prudhomme, M. Synthesis and antimicrobial activities of 3-N-substituted-4, 5-bis(3-indolyl)oxazol-2-ones. Bio. Org. Med. Chem. Lett., 1997, 7, 2503.
8. Viti, G.; Namnicine, R.; Ricci, R.; Pestelline, V.; Abeli, L.; Funo, M. New antagonists of platelet-activating factor containing 2-oxazolidinone or 2-morpholinone. Eur. J. Med. Chem., 1994, 29, 401.
9. Mihaela, M. V. S.; Lenuta, P.; Marcel, P.; Jacques, D.; Cristian, P. Synthesis and biological activity of some new 1, 3, 4-thiadiazole and 1, 2, 4-triazole compounds containing a phenylalanine moiety. Molecules, 2009, 14, 2621.
10. Faroumadi, A.; Mirzaei, M. Shafiee A. Antituberculosis agents, I: Synthesis and antituberculosis activity of 2-aryl-1, 3, 4-thiadiazole derivatives. Pharmazie, 2001, 56, 610.
11. Mamolo M G, Falagiani V,; Zanpier, D.; Vio, L.; Banfi, F. Synthe-sis and antimycobacterial activity of [5-(pyridin-2-yl)-1, 3, 4-thiadiazol-2-ylthio] acetic acid arylidene-hydrazide derivatives. Farmaco, 2001, 56, 587.
12. Zamani, K.; Faghifi, K.; Tefighi, I.; Sharlatzadeh, R. Synthesis and Antimicrobial Activity of Some Pyridyl and Naphthyl Substituted 1, 2, 4-Triazole and 1, 3, 4-Thiadiazole Derivatives. Turk. J. Chem., 2004, 28, 95.
13. Clerici, F.; Pocar, D.; Guido, M.; Loche, A.; Perlini, V.; Brufoni, M. Synthesis of 2-amino-5-sulfanyl-1, 3, 4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity. J. Med. Chem., 2001, 44, 931.
14. Hamidian, H.; Tikari, A. M. Novel synthesis of unsaturated 5(4H)-oxazolone derivatives with using palladium(II) acetate as a catalyst and microwave irradiation in solvent-free condition. Heterocycl. Commun., 2006, 12, 29.
15. Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Calcium acetate cataly-zed synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under sol-vent-free conditions. Tetrahedron Lett., 2004, 45, 425.
16. Khodaei, M. M.; Khosropour, A. R.; Jomor, S. J. H. Efficient and chemoselective conversion of aryl aldehydes to their azalactones catalysed by Bi(III) salts under solvent free conditions. J. Chem. Res., 2003, 10 (4), 638.
17. Rao, P. S.; Venkataraman, R. V. Anhydrous Zinc chloride cata-lysed synthesis of 2-phenyl-4-arylidene-5(4H)-oxazolones, Indian J. Chem., 1994, 33B: 984.
18. Karade, N. N.; Shirodkar, S. G.; Dhoot, B. M.; Waghmare, P. B. Montmorillonite K-10 mediated Erlenmeyer synthesis of 4-arylmethylene-2-phenyl- 5(4H)-oxazolones. J. Chem. Res., 2005, 1(2), 46.
19. Bautista, F. M.; Campelo, J. M.; Luna, D.; Marinas, J. M.; Romero, A. A. Study on dry-media microwave azalactone synthesis on dif-ferent supported KF catalysts: influence of textural and acid-base properties of supports. J. Chem. Soc. Perkin Trans., 2002, 2, 227.
20. Cativiela, C.; Diaz-de-villegas, M. D.; Galvez, J. A. Synthesis and chemical resolution of unique α, β-didehydroamino acids with a chiral axis. Tetrahedron Lett., 1999, 40, 1027.
21. Heravi, M. R. P. Erlenmeyer synthesis of azlactones by sonoche-mical reaction in ionic liquids. J. Univ. Chem. Tech. and Met., 2009, 44, 86.
22. Pasha, M. A.; Jayashankara, V. P.; Venugopala, K. N.; Gopal, K. R. Zinc oxide. (ZnO): An efficient catalyst for the synthesis of 4-arylidine-2-phenyl 5(4H)-oxazolones having antimicrobial acti-vity. J. Pharm.Toxi., 2007, 2, 264.
23. Madhusudana Reddy, M. B.; Pasha, M. A. Molecular Iodine-catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (Azalac-tones) Under Solvent-Free Conditions. Synth Comm., 2010, 40, 1895.
24. Suslick, K. S.; The Year book of Science & the Future Encyclopedia, Britannica, Chicago, 1994; p: 138.
25. Richards, W. T.; Loomis, A. L. The chemical effects of high fre-quency sound waves i. A preliminary survey. J. Am. Chem. Soc., 1927, 49, 3068.
26. Martos, M.; Morales, J.; Sanchez, L.; Ayouchi, R.; Leinen, D.; Martin, F.; Ramos Barrado, J. R. Electrochemical properties of lead oxide films obtained by spray pyrolysis as negative electrodes for lithium secondary batteries. Electrochim. Acta., 2001, 46, 2939.
27. Suryakant, B. S.; Kiran, F. S.; Bapurao, B. S.; Murlidhar, S. S. Nickel nanoparticle-catalyzed facile and efficient one-pot synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions. Tetrahedron Lett., 2009, 50, 1754-1756.
28. 2 particles. Appl. Catal. B., 2002, 36, 161.
29. Hosseini-Sarvari, M.; Sharghi, H.; Etemad, S. Nanocrystalline ZnO for Knoevenagel Condensation and Reduction of the Car-bon, Carbon Double Bond in Conjugated Alkenes. Helv. Chim. Acta., 2008, 91, 715.
30. Suslick, K. S.; Doktycz, S. J. The sonochemistry of zinc powder. J. Am. Chem. Soc., 1989, 111, 2342.
31. Ahluwalia V K, Aggarwal R. Organic Synthesis, Special Tech-niques, 2006.
32. Agawane, S. M.; Nagarkar, J. M. Nano ceria catalyzed synthesis of α-aminophosphonates under ultrasonication. Tetrahedron Lett., 2011, 52, 3499.
33. Seyed, J. A.; Sodeh, S.; Morteza, H. A green protocol for Erlen-meyer-Plöchl reaction by using iron oxide nanoparticles under ul-tra sonic irradiation. Ultrasonics Sonochem., 2013, 20, 408-412 (available online).
34. Madhusudana Reddy M B, Ashoka S, Chandrappa G T, Pasha M A. Nano-MgO: An efficient catalyst for the synthesis of forma-mides from amines and formic acid under MWI. Catal. Lett., 2010, 138, 82.
35. Nagappa, B.; Chandrappa, G. T. Mesoporous nanocrystalline mag-nesium oxide for environmental remediation. Microporous Mesoporous Mater., 2007, 106, 212.
36. Pasha, M. A.; Madhusudana Reddy, M. B. Efficient Method of Synthesis of N, N'-Disubstituted Ureas/Thioureas by a Zinc Chlo-ride Catalyzed Thermal Reaction. Synth. Commun., 2009, 39, 2928.
37. Pasha, M. A.; Jayashankara, V. P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a, j]xanthenes under solvent-free condition. Bioorg. Med. Chem. Lett., 2007, 17, 621.
38. Pasha, M. A.; Jayashankara, V. P.; Swamy, N. R. Simple and Effi-cient Procedure for the One-Pot Synthesis of β-Acetamido-β-aryl- propiophenones by Molecular Iodine-Catalyzed Tandem Reaction. Synth. Commun., 2007, 37, 1551.
39. Madhusudana Reddy, M. B.; Pasha, M. A. Environment friendly protocol for the synthesis of nitriles from aldehydes. Chinese Chem. Lett., 2010, 21, 1025.
40. Pasha, M. A.; Nizam, A. Iodine-Catalyzed, Rapid and Efficient, One-Pot Synthesis of 1, 2-Dihydro-1-arylna-phtho[1, 2e][1, 3]oxazine-3-ones Under Solvent-Free Conditions. Synth. Commun., 2010, 40, 2864.
41. Nizam, A.; Pasha, M. A. p-TSA catalysed efficient synthesis of 1, 2, 4, 5-tetraaryl-imidazoles. J. Saudi Chem. Soc., 2011, 15, 55.
42. Pasha, M. A.; Myint, Yi. Yi. Ultrasound assisted synthesis of δ-chloroesters from tetrahydrofuran and acyl chlorides in the presen-ce of catalytic zinc dus. Ultrasonics Sonochem., 2006, 13, 175.
43. Pasha, M. A.; Jayashankara, V. P. Reduction of arylnitro com-pounds to azoarenes and/or arylamines by Al/NaOH in methanol under ultrasonic conditions. Ultrasonics Sonochem., 2005, 12, 433.
44. 4X (X = Cl, Br, I) in methanol under ultra-sonic conditions. Ultrasonics Sonochem., 2006, 13, 42.
45. 2-alcohol. Ultrasonics Sono-chem., 2005, 12, 437.
46. Rama, K.; Pasha, M. A. Effect of solvent and ultrasound on esteri-fication of phenols. Indian J. Chem., 2002, 41B, 2604.
47. Datta, B.; Pasha, M. A. Cavitational chemistry: A mild and effi-cient multi-component synthesis of amidoalkyl-2-naphthols using reusable silica chloride as catalyst under sonic conditions. Ultraso-nics Sonochem., 2011, 18, 624.
48. Luche, J. L, Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.
49. Timothy, J. M. Ultrasound in synthetic organic chemistry. Chem. Soc. Rev., 1997, 26, 443.
50. 3 in acetone. Ultrasonics Sonochem., 2011, 18, 1124.