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2000
Volume 29, Issue 10
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

This study aimed to synthesize a total of seven halogenated amidostilbenes - using the Heck cross-coupling method. The synthesized stilbenes underwent further reactions with Lewis acids, such as FeCl and SnCl, resulting in imines and indolines , respectively. The structure of all synthesized compounds was elucidated using FTIR, 1D- and 2D-NMR, XRD, and HRMS analysis. Furthermore, the mechanistic details underlying the formation of both imines and indolines were also discussed.

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2025-01-15
2025-06-21
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References

  1. XiaoK. ZhangH. XuanL. ZhangJ. XuY. BaiD. Stilbenoids: Chemistry and bioactivities. In: Studies in Natural Products Chemistry; Atta-ur- Rahman, Ed.; Elsevier: London, 200834453646
    [Google Scholar]
  2. CoggonP. JanesN.F. KingF.E. KingT.J. MolyneuxR.J. MorganJ.W.W. SellarsK. Hopeaphenol, an extractive of the heartwood of Hopea odorata and Balanocarpus heimii.J. Chem. Soc.196540640910.1039/jr9650000406
    [Google Scholar]
  3. CoggonP. McPhailA.T. WallworkS.C. Structure of hopeaphenol: X-ray analysis of the benzene solvate of dibromodeca-O-methylhopeaphenol.J. Chem. Soc. B1970188489710.1039/j29700000884
    [Google Scholar]
  4. PryceR.J. LangcakeP. α-Viniferin: An antifungal resveratrol trimer from grapevines.Phytochemistry19771691452145410.1016/S0031‑9422(00)88809‑3
    [Google Scholar]
  5. SakoM. HosokawaH. ItoT. IinumaM. Regioselective oxidative coupling of 4-hydroxystilbenes: Synthesis of resveratrol and ε-viniferin (E)-dehydrodimers.J. Org. Chem.20046972598260010.1021/jo035791c 15049668
    [Google Scholar]
  6. ThomasN.F. LeeK.C. ParaidathathuT. WeberJ.F.F. AwangK. Manganese triacetate oxidative lactonisation of electron-rich stilbenes possessing catechol and resorcinol substitution (resveratrol analogues).Tetrahedron Lett.200243173151315510.1016/S0040‑4039(02)00484‑7
    [Google Scholar]
  7. ThomasN.F. LeeK.C. ParaidathathuT. WeberJ.F.F. AwangK. RondeauD. RichommeP. Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C.Tetrahedron200258367201720610.1016/S0040‑4020(02)00798‑6
    [Google Scholar]
  8. ThomasN.F. VeluS.S. WeberJ.F.F. LeeK.C. HadiA.H.A. RichommeP. RondeauD. NoorbatchaI. AwangK. A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: Synthetic utility of radical cations in heterocyclic construction.Tetrahedron20046051117331174210.1016/j.tet.2004.10.002
    [Google Scholar]
  9. TakayaY. TerashimaK. ItoJ. HeY.H. TateokaM. YamaguchiN. NiwaM. Biomimic transformation of resveratrol.Tetrahedron20056143102851029010.1016/j.tet.2005.08.023
    [Google Scholar]
  10. AhmadK. ThomasN.F. MukhtarM.R. NoorbatchaI. WeberF.J-F. NafiahM.A. VeluS.S. TakeyaK. MoritaH. LimC.G. HadiA.H.A. AwangK.A. FeCl3-promoted highly atropodiastereoselective cascade reaction: Synthetic utility of radical cations in indolostilbene construction.Tetrahedron20096571504151610.1016/j.tet.2008.11.100
    [Google Scholar]
  11. AzmiM. DinM. KeeC. SuhaimiM. PingA. AhmadK. NafiahM. ThomasN. MohamadK. HoongL. AwangK. Design, synthesis and cytotoxic evaluation of o-carboxamido stilbene analogues.Int. J. Mol. Sci.20131412233692338910.3390/ijms141223369 24287912
    [Google Scholar]
  12. VeluS.S. BuniyaminI. LeeK.C. FerozF. NoorbatchaI. LimC.G. AwangK. WahabI. WeberJ.F.F. Regio‐ and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution.Chemistry20081436113761138410.1002/chem.200801575 19003831
    [Google Scholar]
  13. WangX.F. ZhangY. LinM.B. HouQ. YaoC.S. ShiJ.G. Biomimetic synthesis of active isorhapontigenin dimers.J. Asian Nat. Prod. Res.201416551152110.1080/10286020.2014.913030 24786449
    [Google Scholar]
  14. YadavM.K. MailarK. MasagalliN.J. ChaeS.W. SongJ.J. ChoiW.J. Ruthenium chloride-induced oxidative cyclization of trans-resveratrol to (±)-ε-viniferin and antimicrobial and antibiofilm activity against Streptococcus pneumoniae.Front. Pharmacol.20191089010.3389/fphar.2019.00890 31474855
    [Google Scholar]
  15. TamboliV.F. ReN. ColettiC. DefantA. ManciniI. TosiP. A joint experimental and theoretical investigation on the oxidative coupling of resveratrol induced by copper and iron ions.Int. J. Mass Spectrom.2012319-320556310.1016/j.ijms.2012.05.010
    [Google Scholar]
  16. EnglerT.A. GfesserG.A. DraneyB.W. Lewis acid-promoted reactions of unsymmetrically substituted stilbenes with 2-methoxy-1,4-benzoquinones: Stereoselective synthesis of trans-2,3-diaryl-2,3-dihydrobenzofurans.J. Org. Chem.199560123700370610.1021/jo00117a021
    [Google Scholar]
  17. WeberJ.F.F. WahabI.A. MarzukiA. ThomasN.F. KadirA.A. HadiA.H.A. AwangK. LatiffA.A. RichommeP. DelaunayJ. Heimiol A, a new dimeric stilbenoid from Neobalanocarpus heimii.Tetrahedron Lett.200142294895489710.1016/S0040‑4039(01)00772‑9
    [Google Scholar]
  18. KeeC.H. AriffinA. AwangK. NoorbatchaI. TakeyaK. MoritaH. LimC.G. ThomasN.F. Cyclization vs. cyclization/dimerization in o-amidostilbene radical cation cascade reactions: The amide question.Molecules20111697267728710.3390/molecules16097267 21869754
    [Google Scholar]
  19. SilvaT.S. RodriguesM.T.Jr SantosH. ZeolyL.A. AlmeidaW.P. BarcelosR.C. GomesR.C. FernandesF.S. CoelhoF. Recent advances in indoline synthesis.Tetrahedron201975142063209710.1016/j.tet.2019.02.006
    [Google Scholar]
  20. BoalB.W. SchammelA.W. GargN.K. An interrupted fischer indolization approach toward fused indoline-containing natural products.Org. Lett.200911153458346110.1021/ol901383j 19601608
    [Google Scholar]
  21. IvanovD.S. ZaitsevaE.R. SmirnovA.Y. RustamovaD.A. MikhaylovA.A. SychevaM.A. GluschenkoD.A. BaleevaN.S. BaranovM.S. Chemodivergent spirocyclization of 2-sec-aminobenzilidene imidazolones: Lewis versus Brønsted acids catalysis.Adv. Synth. Catal.202236491587159510.1002/adsc.202200109
    [Google Scholar]
  22. AnuarN. TaibM.M.N.A. HanafiahM.K. ShammaryA.A.A.K. ShalanN.S.N. HumaidiC.S.N.I. AwangK. Synthesis of 1ʹ-acetoxychavicol acetate (ACA) analogues and their inhibitory activities against methicillin-resistant Staphylococcus aureus.J. Physiol. Sci.202031310111110.21315/jps2020.31.3.8
    [Google Scholar]
  23. O’DonnellM.J. PoltR.L. A mild and efficient route to Schiff base derivatives of amino acids.J. Org. Chem.198247132663266610.1021/jo00134a030
    [Google Scholar]
  24. TogoH. Advanced free radical reactions for organic synthesis.TokyoElsevier2004
    [Google Scholar]
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