Skip to main content
SpringerLink
Log in

Synthesis of conjugated (E,E)-1,3-diene-containing troponoid-based compounds

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Through exploration of the electrophilic substitution reaction of 3-((2E,4E)-5-phenylpenta-2,4-dienoyl)-2-hydroxy-2,4,6-cycloheptatrien-1-one (3-((2E,4E)-5-phenylpenta-2,4-dienoyl)tropolone) with halogen and diazonium salts as well as the nucleophilic cyclisation reaction with hydroxylamine hydrochloride and substituted phenylhydrazine hydrochlorides by employing our reliable methods, we have synthesised a series of new (E,E)-1,3-diene-bearing troponoid-based compounds. All the newly synthesised molecules represent an issue of great interest, since the presence of conjugated 1,3-diene moiety can be developed further via other reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Adlington, R. M., Baldwin, J. E., Mayweg, A. V. W., & Pritchard, G. J. (2002). Biomimetic cycloaddition approach to tropolone natural products via a tropolone orthoquinone methide. Organic Letters, 4, 3009–3011. DOI: 10.1021/ol026467r.

    Article  CAS  Google Scholar 

  • Albrecht, U., Van Nguyen, T. H., & Langer, P. (2004). Synthesis of 4,5-benzotropones by cyclization of 1,3-bis-silyl enol ethers with 1,2-dialdehydes. Journal of Organic Chemistry, 69, 3417–3424. DOI: 10.1021/jo049736v.

    Article  CAS  Google Scholar 

  • Angawi, R. F., Swenson, D. C., Gloer, J. B., & Wicklow, D. T. (2003). Malettinin A: a new antifungal tropolone from an unidentified fungal colonist of Hypoxylon stromata (NRRL 29110). Tetrahedron Letters, 44, 7593–7596. DOI: 10.1016/j.tetlet.2003.08.057.

    Article  CAS  Google Scholar 

  • Azizian, J., Ramazani, A., & Haji, M. (2011). Synthesis of dialkyl 2-(alkylamino)-4,9-dihydro-9-oxocyclohepta[b]pyran-3,4-dicarboxylates. Helvetica Chimica Acta, 94, 371–375. DOI: 10.1002/hlca.201000222.

    Article  CAS  Google Scholar 

  • Barceló, M., Raviña, E., Masaguer, C. F., Domínguez, E., Areias, F. M., Brea, J., & Loza, M. I. (2007). Synthesis and binding affinity of new pyrazole and isoxazole derivatives as potential atypical antipsychotics. Bioorganic & Medicinal Chemistry Letters, 17, 4873–4877. DOI: 10.1016/j.bmcl.2007.06.045.

    Article  Google Scholar 

  • Bazin, M. A., Kihel, L. E., Jouanne, M., Lancelot, J. C., & Rault, S. (2008). Synthesis of new avenalumic carboxamide derivatives in the ferulic series. Synthetic Communications, 38, 3947–3959. DOI: 10.1080/00397910802238817.

    Article  CAS  Google Scholar 

  • Bentley, R. (2008). A fresh look at natural tropolonoids. Natural Product Reports, 25, 118–138. DOI: 10.1039/b711474e.

    Article  CAS  Google Scholar 

  • Bhargava, G., Mohan, C., & Mahajan, M. P. (2008). Lewis acid promoted imino Diels-Alder reactions of 5-dienyl pyrimidinones with N-aryl/naphthyl imines: synthesis of novel quinoline/benzoquinoline derivatives. Tetrahedron, 64, 3017–3024. DOI: 10.1016/j.tet.2008.01.041.

    Article  CAS  Google Scholar 

  • Boguszewska-Chachulska, A. M., Krawczyk, M., Najda, A., Kopańska, K., Stankiewicz-Drogoń, A., Zagórski-Ostoja, W., & Bretner, M. (2006). Searching for a new anti-HCV therapy: Synthesis and properties of tropolone derivatives. Biochemical and Biophysical Research Communications, 341, 641–647. DOI: 10.1016/j.bbrc.2006.01.015.

    Article  CAS  Google Scholar 

  • Cai, M. Z., Wang, D., & Wang, P. P. (2006). Novel stereoselective synthesis of 1-substituted 1,3-dien-2-yl sulfides via Stille coupling reactions of (E)-α-stannylvinyl sulfides with alkenyl iodides. Journal of Organometallic Chemistry, 691, 737–740. DOI: 10.1016/j.jorganchem.2005.10.012.

    Article  CAS  Google Scholar 

  • Chang, M., Li, Y., & Gao, W. (2011). A facile synthesis of new troponoid-bearing flavonoid-like compounds. Heterocycles, 83, 1631–1640. DOI: 10.3987/com-11-12223.

    CAS  Google Scholar 

  • Conti, C., & Desideri, N. (2010). New 4H-chromen-4-one and 2H-chromene derivatives as anti-picornavirus capsid-binders. Bioorganic & Medicinal Chemistry, 18, 6480–6488. DOI: 10.1016/j.bmc.2010.06.103.

    Article  CAS  Google Scholar 

  • Ganjeie, B., Ramazani, A., & Kazemizadeh, A. R. (2007). Synthesis of electron-poor pyrazole derivatives from in-situ generated stabilized phosphorus ylides. Phosphorus, Sulfur, and Silicon and the Related Elements, 182, 1703–1708. DOI: 10.1080/10426500701290771.

    Article  CAS  Google Scholar 

  • Gao, W. T., Jin, Z. T., Yin, B. Z., & Imafuku, K. (1989). Synthesis and reactions of halo-, nitro-, and arylazo-substituted 3- cinnamoyltropolones. Formation of styryl-substituted heterocycle-fused troponoid compounds. Journal of Heterocyclic Chemistry, 26, 371–375. DOI: 10.1002/jhet.5570260219.

    Article  CAS  Google Scholar 

  • Gao, W., Li, Y., Zhang, H., Chang, M., & Imafuku, K. (2009a). Oxidative cyclization of 3-cinnamoyltropolones with I2/DMSO/H2SO4 system. Journal of Heterocyclic Chemistry, 46, 1107–1112. DOI: 10.1002/jhet.150.

    Article  CAS  Google Scholar 

  • Gao, W. T., Sun, M. C., & Li, Y. (2010a). Synthesis and reactions of halo-, arylazo-substituted 3-(3-(1-naphthyl)acryloyl) tropolones. Formation of (naphthalen-1-yl)vinyl)substituted heterocycle-fused troponoid compounds. Chinese Journal of Chemistry, 28, 1409–1416. DOI: 10.1002/cjoc.201090241.

    Article  CAS  Google Scholar 

  • Gao, W., Sun, M., Li, Y., Li, W., & Imafuku, K. (2009b). Synthesis and reactions of halo- and arylazo-substituted 3-(3-(2-naphthyl)acryloyl)tropolones: Formation of (naphthalen-2-yl)vinyl) substituted heterocycle-fused troponoid compounds. Journal of Heterocyclic Chemistry, 46, 1302–1308. DOI: 10.1002/jhet.243.

    Article  CAS  Google Scholar 

  • Gao, W., Zhang, X., Li, Y., Liu, H., & Imafuku, K. (2010b). First synthesis of 2-tropolonylquinoline-4-carboxylic acid derivatives via Pfitzinger reaction in water. Heterocycles, 81, 1689–1696. DOI: 10.3987/com-10-11960.

    Article  CAS  Google Scholar 

  • Gao, W. T., & Zheng, Z. (2000). Study on synthesis of heterocycle-fused troponoid compounds. Chinese Chemical Letters, 11, 503–504.

    CAS  Google Scholar 

  • Hong, S. H., Kim, H., Seo, Y., Lee, S. H., Cha, J. K., & Kim, Y. G. (2010). Total synthesis of pareitropone via radical anion coupling. Organic Letters, 12, 3954–3956. DOI: 10.1021/ol1017849.

    Article  CAS  Google Scholar 

  • Ignatowska, J., & Dmowski, W. (2006). Sodium dithionite initiated addition of 1-bromo-1-chloro-2,2,2-trifluoroethane to allylaromatics: Facile synthesis of conjugated dienes substituted with terminal CF3 group. Journal of Fluorine Chemistry, 127, 720–729. DOI: 10.1016/j.jfluchem.2006.01.007.

    Article  CAS  Google Scholar 

  • Li, Y., & Gao, W. (2010). Synthesis of 5,7-dibromotropono[c] pyrazole derivatives. Heterocycles, 81, 2617–2623. DOI: 10.3987/com-10-12045.

    Article  CAS  Google Scholar 

  • Liu, H. L., Jiang, H. F., Xu, L., & Zhan, H. Y. (2007). Solventfree heterogeneous organocatalysis: stereoselective isomerization of α,β-ynones to (E,E)-α,β-γ,δ-dienones catalyzed by polymer-supported tertiaryphosphines. Tetrahedron Letters, 48, 8371–8375. DOI: 10.1016/j.tetlet.2007.09.093.

    Article  CAS  Google Scholar 

  • Mazzeo, M., Lamberti, M., Tuzi, A., Centore, R., & Pellecchia, C. (2005). New anilinotropone-based titanium complexes: synthesis, characterization and application as catalysts for olefin polymerization. Dalton Transactions, 2005, 3025–3031. DOI: 10.1039/b506079f.

    Article  Google Scholar 

  • Mori, A., Kubo, K., Takemoto, M., & Ujiie, S. (2005). Nonsymmetric calamitic liquid crystal dimers containing troponoid and benzenoid units. Liquid Crystals, 32, 1021–1029. DOI: 10.1080/02678290500183599.

    Article  CAS  Google Scholar 

  • Morsali, A., & Ramazani, A. (2005). Syntheses and characterization of Zn(II), Cd(II) and Hg(II) complexes with 5-methyl-1-(2′-pyridyl)pyrazole-3-carboxamide (MPy Pz CA) ligand. Journal of Coordination Chemistry, 58, 751–758. DOI: 10.1080/00958970500070384.

    Article  CAS  Google Scholar 

  • Morsali, A., Ramazani, A., Babaee, M., Jamali, F., Gouranlou, F., Arjmandfar, H., & Yanovsky, A. (2003). Mixed-anion Cu(II) complexes with 3-(pyridin-2-yl)pyrazole (L), syntheses and X-ray crystal structure of [Cu(L)2Br]ClO4 (L = 3-(pyridin-2-yl)pyrazole). Journal of Coordination Chemistry, 56, 455–461. DOI: 10.1080/00958970305496.

    Article  CAS  Google Scholar 

  • Nishimura, T., Yasuhara, Y., Sawano, T., & Hayashi, T. (2010). Iridium/chiral diene-catalyzed asymmetric 1,6-addition of arylboroxines to α,β,γ,δ-unsaturated carbonyl compounds. Journal of the American Chemical Society, 132, 7872–7873. DOI: 10.1021/ja1034842.

    Article  CAS  Google Scholar 

  • Noshiranzadeh, N., & Ramazani, A. (2008a). The reaction of phenylhydrazine with sterically congested stabilized phosphorus ylides in the presence of silica gel powder in solvent-free conditions: A novel synthesis of fully substituted pyrazole derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 1109–1115. DOI: 10.1080/10426500701569448.

    Article  CAS  Google Scholar 

  • Noshiranzadeh, N., & Ramazani, A. (2008b). Triphenylphosphine catalyzed stereoselective addition of 3,5-diphenyl-1H-pyrazole to acetylenic esters. Phosphorus, Sulfur, and Silicon and the Related Elements, 183, 144–149. DOI: 10.1080/10426500701557336.

    Article  CAS  Google Scholar 

  • Ramazani, A., Amini, I., & Massoudi, A. (2006). Dipotassium hydrogen phosphate powder-catalyzed stereoselective synthesis of N-vinyl pyrazoles in solvent-free conditions. Phosphorus, Sulfur, and Silicon and the Related Elements, 181, 2225–2229. DOI: 10.1080/10426500600614683.

    Article  CAS  Google Scholar 

  • Ramazani, A., & Bodaghi, A. (2004). Synthesis of highly electron-poor alkenes from in situ generated stabilized phosphorus ylides and ninhydrin via intermolecular Wittig reaction. Phosphorus, Sulfur, and Silicon and the Related Elements, 179, 1615–1620, DOI: 10.1080/10426500490466166.

    Article  CAS  Google Scholar 

  • Seephonkai, P., Isaka, M., Kittakoop, P., Trakulnaleamsai, S., Rattanajak, R., Tanticharoen, M., & Thebtaranonth, Y. (2001). A new tropolone from the insect pathogenic fungus Cordyceps sp. BCC 1681. Journal of Antibiotics, 54, 751–752.

    Article  CAS  Google Scholar 

  • Wakabayashi, H., Yokoyama, K., Hashiba, K., Hashimoto, K., Kikuchi, H., Nishikawa, H., Kurihara, T., Satoh, K., Shioda, S., Muto, S., Terakubo, S., Nakashima, H., Motohashi, N., & Sakagami, H. (2003). Cytotoxic acticvity of tropolones against human oral tumor cell lines. Anticancer Research, 23, 4757–4763.

    CAS  Google Scholar 

  • Xiao, W. J., Vasapollo, G., & Alper, H. (2000). Highly regioselective thiocarbonylation of conjugated dienes via palladiumcatalyzed three-component coupling reactions. Journal of Organic Chemistry, 65, 4138–4144. DOI: 10.1021/jo000231o.

    Article  CAS  Google Scholar 

  • Yamato, M., Hashigaki, K., Kokubu, N., Tsuruo, T., & Tashiro, T. (1984). Synthesis and antitumor activity of tropolone derivatives. 1. Journal of Medicinal Chemistry, 27, 1749–1753. DOI: 10.1021/jm00378a041.

    Article  CAS  Google Scholar 

  • Zhang, B., Gao, W., & Piao, M. (1995). Condensation reaction of 3-acetyltropolone with aromatic aldehydes (TMB). Chemistry and Adhesion, 3, 134–135.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Superfine Chemicals, Bohai University, 121000, Jinzhou, China

    Wen-Tao Gao, Yan Yan & Yang Li

Authors
  1. Wen-Tao Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yan Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Wen-Tao Gao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gao, WT., Yan, Y. & Li, Y. Synthesis of conjugated (E,E)-1,3-diene-containing troponoid-based compounds. Chem. Pap. 66, 691–698 (2012). https://doi.org/10.2478/s11696-012-0155-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-012-0155-1

Keywords

Search

Navigation