Skip to content
2000
Volume 22, Issue 1
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

An organocatalytic, one-pot four-center two-component coupling reaction has been developed for the synthesis of tetrahydro-1,7-chromeno[3,4-]chromen-1-one derivatives. The reaction proceeds smoothly in the presence of 5 mol% DL-Proline in methanol under reflux conditions. This method involves the Knoevenagel condensation of -alkynyl tethered 2-hydroxybenzaldehydes with cyclic 1,3-diketones followed by an intramolecular hetero-Diels-Alder reaction. Novel classes of oxygen containing polycyclic frameworks are prepared in good yields by using this approach.

© 2025 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/loc/10.2174/0115701786312736240604093915
2024-06-13
2025-07-15

  • From This Site

    /content/journals/loc/10.2174/0115701786312736240604093915
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. ShivaputraA.P. RenukadeviP. LawrenceM.P. DuaneD.M. Future Med. Chem.201351647166010.4155/fmc.13.12624047270
     [Google Scholar]
  2. VinitR. JintaeL. Front Chem.2020862310.3389/fchem.2020.0062332850645
     [Google Scholar]
  3. XiaoS.H. XiongY. ZhangX-X. CaoS. MingH.Y. JianG.L. WenY.Y. LingY.K. Tetrahedron201470294405441110.1016/j.tet.2014.04.052
     [Google Scholar]
  4. LutfunN. AnupamD.T. DeepaN. SushmitaN. AmanM. FyazM.D.I. SatyajitD.S. Molecules202025498310.3390/molecules2521498333126458
     [Google Scholar]
  5. AhmedM.M.E.S. MahboubaB.N. BahlulK.R. NabilA.S. KhaledM.K. ARKIVOC20072007168391
     [Google Scholar]
  6. AngelesM.G. JoséL. Bioorg. Med. Chem. Lett.1997731653170
     [Google Scholar]
  7. StephenJ.M. MichaelA.C. FrederickS.F. JamesW.P. Cancer Res.197535375037541192431
     [Google Scholar]
  8. RamendraP. VishnuJ.R. Chem. Rev.2014114104761052610.1021/cr500075s25303539
     [Google Scholar]
  9. ShilpaA.W. TanayK. TuanliY. RichardC.L. J. Org. Chem.2007721347135310.1021/jo062234s17288382
     [Google Scholar]
  10. ZhiZ. MengyaoB. LixinZ. HuiG. JunjunH. XiawenL. XiyongY. XingweiL. WeiY. Org. Lett.2018203892389610.1021/acs.orglett.8b0147729897772
     [Google Scholar]
  11. WangQ. FinnM.G. Org. Lett.2000240634065
     [Google Scholar]
  12. RahulM. GhanashyamB. J. Org. Chem.2020854627463610.1021/acs.joc.9b0336632151132
     [Google Scholar]
  13. ShuiX.L. ChunM.J. BoY.Y. XiangL.C. Synthesis201648407412
     [Google Scholar]
  14. MajidM.H. TaherehA. MahdiehG. BaharehH. HodaH. RSC Advances2015510199910207510.1039/C5RA17488K
     [Google Scholar]
  15. AmitA.K. DavidO.M. LouiseN.D. GrahamJ.B. Org. Biomol. Chem.201197196720610.1039/c1ob05867c21858320
     [Google Scholar]
  16. SubburethinamR. RajagopalN. Tetrahedron Lett.2011524857486010.1016/j.tetlet.2011.07.033
     [Google Scholar]
  17. HeatherT. RobertA.B. Org. Lett.200464913500610.1021/ol047984815606098
     [Google Scholar]
  18. ShanmugasundaramM. ManikandanS. RaghunathanR. Tetrahedron20025859971003
     [Google Scholar]
  19. LutzF.T. Chem. Rev.19969611513610.1021/cr950027e11848746
     [Google Scholar]
  20. LutzH.D. Yifa.Z. Angew. Chem. Int. Ed.19993824363910.1002/(SICI)1521‑3773(19991216)38:24<3639::AID‑ANIE3639>3.0.CO;2‑2
     [Google Scholar]
  21. TietzeL.F. KettschauG. GewertJ.A. Curr. Org. Chem.199821962
     [Google Scholar]
  22. LutzF.T. ChristianO. FrankH. Can. J. Chem.20017915111514
     [Google Scholar]
  23. AleksandraP. Top. Curr. Chem.20163742410.1007/s41061‑016‑0026‑2
     [Google Scholar]
  24. ManickamB. GovindanS. DamodharanK. Org. Lett.2009114466446910.1021/ol901228j19775188
     [Google Scholar]
  25. BaddulaD. ManishaS. Bioorg. Med. Chem. Lett.20122219951999
     [Google Scholar]
  26. MingchangW. JunhangY. FangL. CunguiC. Gangguo.Z. Org. Biomol. Chem.2019175684568710.1039/C9OB00836E31134253
     [Google Scholar]
  27. BhagyashriD.P. TusharR.S. GaurangkumarC.B. NarsidasJ.P. RajniK. VivekK.G. J. Org. Chem.2016814955496410.1021/acs.joc.6b0010727171909
     [Google Scholar]
  28. GowravaramS. NarjisF. Adv. Synth. Catal.200534713531355
     [Google Scholar]
  29. ParmarN.J. TeraiyaS.B. BaradH.A. SharmaD. Synth. Commun.20134315771586
     [Google Scholar]
  30. PanditR.P. LeeY.R. Mol. Divers.2014183950
     [Google Scholar]
  31. MukundJ.H. GuyS. ChouT.Y. Tetrahedron Lett.20115243374341
     [Google Scholar]
  32. MaliheJ.K. SaeedB. HamidR.B. FrankR. JürgenH.G. Tetrahedron Lett.2008496965696810.1016/j.tetlet.2008.09.079
     [Google Scholar]
  33. MostafaK. FirouzM.M. Tetrahedron Lett.2009506723672710.1016/j.tetlet.2009.09.106
     [Google Scholar]
  34. PedroM.A. GabrielaF. AlejandroT. AnaE.B. J. Org. Chem.2016819738975610.1021/acs.joc.6b0181827680299
     [Google Scholar]
  35. MaliheJ.K. MohammadR.H. SaeedB. MohammadR.B. HamidR.B. Helv. Chim. Acta201295526010.1002/hlca.201100237
     [Google Scholar]
  36. ManickamB. GovindanS. Tetrahedron Lett.2014551765177010.1016/j.tetlet.2014.01.126
     [Google Scholar]
  37. HaiboT. HongxinL. XinzhengC. HuiyuC. ShengxiangQ. Org. Biomol. Chem.2015139977998310.1039/C5OB01636C26287502
     [Google Scholar]
  38. TanH. ChenX. ChenH. QiuS. Eur. J. Org. Chem.20152249564963
     [Google Scholar]
  39. RamacharyD.B. ChowdariN.S. BarbasC.F.III Angew. Chem.2003115354365436910.1002/ange.200351916
     [Google Scholar]
  40. YadavJ.S. Subba ReddyB.V. Hara GopalA.V. XieZ. Nageshwar RaoR. Tetrahedron Lett.20105123052308
     [Google Scholar]
  41. CCDC 2286103for 5e contains the supplementary crystallographic data for this paper
     [Google Scholar]
/content/journals/loc/10.2174/0115701786312736240604093915
Loading
Organocatalytic Domino Knoevenagel Hetero-Diels-Alder Reaction for the Synthesis of Chromenopyran Derivatives
Lett. Org. Chem. 22, 78 (2025); https://doi.org/10.2174/0115701786312736240604093915
/content/journals/loc/10.2174/0115701786312736240604093915
/content/journals/loc/10.2174/0115701786312736240604093915
Loading

Data & Media loading...

Supplements

Supplementary material is available on the publisher's website along with the published article.

file format download Download

  • Article Type:     Research Article
Keyword(s): 1,3-diketones; cyclohexane-1,3-dione; DL-Proline; fused chromenes; hetero-Diels-Alder reaction; O-Alkynyl salicylaldehydes; organocatalyst; propargyl bromide

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test