MODIFICATION OF NOVEL ISOXAZOLINES OF FULVENE DERIVATIVES WITH 1,3-DIPOLAR CYCLOADDITION REACTION

Yıl 2018, Cilt: 5 Sayı: 3, 1351 - 1360, 01.09.2018

Omer Gunkara

https://doi.org/10.18596/jotcsa.484885

Öz

In this work, 1,3-Dipolar cycloaddition
reactions were studied to synthesize fulvene derivatives containing isoxazoline groups in good yields.  1,3-Dipolar cycloaddition reactions are among the
most useful strategies for the preparation of organic compounds. All newly synthesized fulvene compounds were
structurally characterized by FTIR, ¹H, ¹³C NMR and GC/MS
analyses.

Anahtar Kelimeler

Cycloaddition, Fulvenes, Heterocycles, Isoxazoles

Kaynakça

• 1. Gothelf KV, Jorgensen KA. Asymmetric 1,3-Dipolar Cycloaddition Reactions. Chem Rev. 1998;98(2):863-910.
• 2. Pandey G, Banerjee P, Gadre SR. Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides. Chem Rev. 2006;106(11):4484-517.
• 3. Stanley LM, Sibi MP. Enantioselective copper-catalyzed 1,3-dipolar cycloadditions. Chem Rev. 2008;108(8):2887-902.
• 4. Adrio J, Carretero JC. Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides. Chem Commun (Camb). 2011;47(24):6784-94.
• 5. Huisgen R, Mloston G, Polborn K. 1,3-Dipolar Activity in Cycloadditions of an Aliphatic Sulfine(,)(1). J Org Chem. 1996;61(19):6570-4.
• 6. Woodward RB. Recent advances in the chemistry of natural products. Science. 1966;153(3735):487-93.
• 7. Hoffmann R, Woodward RB. Orbital symmetry control of chemical reactions. Science. 1970;167(3919):825-31.
• 8. Furukawa M, Sugita M, Kojima Y. Reaction of epoxides. V. 1,3-Dipolar cycloaddition reactions of epoxides with carbon-nitrogen double bond compounds. Chem Pharm Bull (Tokyo). 1974;22(7):1468-76.
• 9. Kano T, Hashimoto T, Maruoka K. Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral Lewis acid. J Am Chem Soc. 2005;127(34):11926-7.
• 10. Siadati SA, Mahboobifar A, Nasiri R. A theoretical study on the reaction pathways and the mechanism of 1,3- dipolar cycloaddition of vinyl acetylene and methyl azide. Comb Chem High Throughput Screen. 2014;17(8):703-8.
• 11. Beckhaus R, Lutzen A, Haase D, Saak W, Stroot J, Becke S, et al. A Novel Route to Fulvene Complexes of Titanium-Diastereoselective Complexation of Pentafulvenes to Cyclopentadienyltitanium Fragments. Angew Chem Int Ed Engl. 2001;40(11):2056-8.
• 12. Bryan CS, Lautens M. A tandem catalytic approach to methyleneindenes: mechanistic insights into gem-dibromoolefin reactivity. Org Lett. 2010;12(12):2754-7.
• 13. Ye S, Yang X, Wu J. Rapid access to 1-methyleneindenes via palladium-catalyzed tandem reactions of 1-(2,2-dibromovinyl)-2-alkynylbenzenes with arylboronic acids. Chem Commun (Camb). 2010;46(17):2950-2.
• 14. Ye S, Gao K, Zhou H, Yang X, Wu J. Synthesis of 1-methyleneindenes via palladium-catalyzed tandem reactions. Chem Commun (Camb). 2009(36):5406-8.
• 15. Abdur Rahman SM, Sonoda M, Ono M, Miki K, Tobe Y. Novel synthesis of bridged phenylthienylethenes and dithienylethenes via Pd-catalyzed double-cyclization reactions of diarylhexadienynes. Org Lett. 2006;8(6):1197-200.
• 16. Schmittel M, Vavilala C. Kinetic isotope effects in the thermal C2-C6 cyclization of enyne-allenes: experimental evidence supports a stepwise mechanism. J Org Chem. 2005;70(12):4865-8.
• 17. Kovalenko SV, Peabody S, Manoharan M, Clark RJ, Alabugin IV. 5-Exo-dig radical cyclization of enediynes: the first synthesis of tin-substituted benzofulvenes. Org Lett. 2004;6(14):2457-60.
• 18. Bekele T, Christian CF, Lipton MA, Singleton DA. "Concerted" transition state, stepwise mechanism. Dynamics effects in C2-C6 enyne allene cyclizations. J Am Chem Soc. 2005;127(25):9216-23.
• 19. Clegg NJ, Paruthiyil S, Leitman DC, Scanlan TS. Differential response of estrogen receptor subtypes to 1,3-diarylindene and 2,3-diarylindene ligands. J Med Chem. 2005;48(19):5989-6003.
• 20. Krief A, Laval AM. Coupling of Organic Halides with Carbonyl Compounds Promoted by SmI(2), the Kagan Reagent. Chem Rev. 1999;99(3):745-78.
• 21. Hong BC, Shr YJ, Wu JL, Gupta AK, Lin KJ. Novel [6 + 2] cycloaddition of fulvenes with alkenes: a facile synthesis of the anislactone and hirsutane framework. Org Lett. 2002;4(13):2249-52.
• 22. Barluenga J, Martinez S, Suarez-Sobrino AL, Tomas M. New reaction pathways for Fischer carbene complexes: [6 + 3] cycloaddition of chromium alkenyl carbene complexes with fulvenes. J Am Chem Soc. 2001;123(44):11113-4.
• 23. Coskun N, Ma J, Azimi S, Gartner C, Erden I. 1,2-Dihydropentalenes from fulvenes by [6 + 2] cycloadditions with 1-isopropenylpyrrolidine. Org Lett. 2011;13(22):5952-5.
• 24. Cassady JM, Baird WM, Chang CJ. Natural-Products as a Source of Potential Cancer Chemotherapeutic and Chemopreventive Agents. J Nat Prod. 1990;53(1):23-41.
• 25. Vijesh AM, Isloor AM, Shetty P, Sundershan S, Fun HK. New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents. Eur J Med Chem. 2013;62:410-5.
• 26. Soares MIL, Brito AF, Laranjo M, Paixao JA, Botelho MF, Melo TMVDPE. Chiral 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles with anti-breast cancer properties. Eur J Med Chem. 2013;60:254-62.
• 27. Kamal A, Bharathi EV, Reddy JS, Ramaiah MJ, Dastagiri D, Reddy MK, et al. Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents. Eur J Med Chem. 2011;46(2):691-703.
• 28. Shi L, Hu R, Wei Y, Liang Y, Yang Z, Ke S. Anthranilic acid-based diamides derivatives incorporating aryl-isoxazoline pharmacophore as potential anticancer agents: design, synthesis and biological evaluation. Eur J Med Chem. 2012;54:549-56.
• 29. Shaala LA, Youssef DT, Sulaiman M, Behery FA, Foudah AI, Sayed KA. Subereamolline A as a potent breast cancer migration, invasion and proliferation inhibitor and bioactive dibrominated alkaloids from the Red Sea sponge Pseudoceratina arabica. Mar Drugs. 2012;10(11):2492-508.
• 30. Sadashiva MP, Basappa, NanjundaSwamy S, Li F, Manu KA, Sengottuvelan M, et al. Anti-cancer activity of novel dibenzo[b,f]azepine tethered isoxazoline derivatives. BMC Chem Biol. 2012;12:5.
• 31. Miller SA, Bercaw JE. Mechanism of isotactic polypropylene formation with C-1-symmetric metallocene catalysts. Organometallics. 2006;25(15):3576-92.
• 32. Ocal N, Bagdatli E, Arslan M. Diels-Alder reactions of new methoxysubstituted-6-arylfulvenes. Turk J Chem. 2005;29(1):7-16.
• 33. Puerto Galvis CE, Kouznetsov VV. An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model. Org Biomol Chem. 2013;11(3):407-11.
• 34. Alam MI, Alam MA, Alam O, Nargotra A, Taneja SC, Koul S. Molecular modeling and snake venom phospholipase A(2) inhibition by phenolic compounds: Structure-activity relationship. Eur J Med Chem. 2016;114:209-19.