Skip to main content
SpringerLink
Log in

Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

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

Abstract

Reaction of equimolar amounts of 2,4(1H,3H)-quinolinediones and diethyl acetylenedicarboxylate in absolute ethanol, containing catalytic triethylamine, gave ethyl 5,6-dihydro-2,5-dioxo-6,9-disubstituted-2H-pyrano[3,2-c]quinoline-4-carboxylates in good yields. In a different manner, reaction of two equivalents of dialkyl acetylenedicarboxylates with one equivalent of 2,4(1H,3H)-quinolinediones afforded dialkyl 2(4-oxo-1,4-dihydroquinolin-3-yl)fumarates in good yields. The structures of the products were elucidated by 1H NMR, 13C NMR, two-dimensional NMR, IR, mass spectra and elemental analyses.

Graphical Abstract

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

Scheme 1
Fig. 1
Scheme 2
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Aly AA, El-Shaieb KM (2007) Reaction of N-imidoylthioureas with dimethyl acetylenedicarboxylate: synthesis of new 1,3,5-thiadiazepines. J Chem Res 2007:563–565. doi:10.3184/030823407X255579

  • Aly AA, Hopf H, Ernst L, Dix I, Jones PG (2006) New cycloadditions of (E)-N,α-dimethyl-α-(4-[2.2]para-cylophanyl)-nitrone. Eur J Org Chem 2006:3001–3006. doi:10.1002/ejoc.200500745

  • Aly AA, Ahmed EK, El-Mokadam KM (2007) Reactions of aroylthioureas with acetylenic esters and dibenzoyl ethylene. Selectivity towards the formation of new 1,3-thiazines. J Heterocycl Chem 44:1431–1438

    Article  CAS  Google Scholar 

  • Aly AA, Brown AB, Hasaan AA, El-Shaieb KM, Bedair TMI (2009) Carbamothioates in the synthesis of diaroyl sulfides; selectivity of diaroyl sulfides and their addition to acetylenic and ethylenic deficient compounds. Arkivoc viii:66–77

    Google Scholar 

  • Aly AA, Brown AB, Radwan MF, Gamal-Eldeen AM, Abdel-Aziz M, Abuo-Rahma GA, Ramadan M (2010) Thieno[2,3-d]pyrimidines in the synthesis of antitumor and antioxidant agents. Arch Pharm 343:301–309

    CAS  Google Scholar 

  • Aly AA, Brown AB, Hassan AA (2014) Heterocycles from the reaction of thione groups with acetylenic bonds. Adv Heterocycl Chem 113:245–304

    Article  CAS  Google Scholar 

  • Anary-Abbasinejad M, Anaraki-Ardakani H, Ezadi A, Hassanabadi A (2007) Three-component reaction between triphenylphosphine, acetylenic esters and 4-hydroxycoumarin, 4-(phenylamino)coumarin, 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-1-methylquinolin-2(1H)-one. J Chem Res 2007:605–608. doi:10.3184/030823407X256154

  • Asghari S, Ramezani S (2014) An efficient three-component synthesis of pyranoquinoline derivatives. J Heterocycl Chem 51:233–236

    Article  CAS  Google Scholar 

  • Ayafor JF, Sondengam BL, Ngadjui BT (1982) Veprisinium salt, a novel antibacterial quaternary alkaloid from Vepris louisii. Planta Med 44:139–142

    Article  CAS  Google Scholar 

  • Bandaru S, Majji RK, Bassa S, Chilla PN, Yellapragada R, Vasamsetty S, Jeldi RK, Korupolu RB, Sanasi PD (2016) Magnetic Nano cobalt ferrite catalyzed synthesis of 4H-pyrano[3,2-h]quinoline derivatives under microwave irradiation. Green Sust Chem 6:101–109

    Article  Google Scholar 

  • Barriga S, Fuertes P, Marcos CF, Torroba T (2004) Synthesis of highly branched sulfur–nitrogen heterocycles by cascade cycloadditions of [1,2]dithiolo[1,4]thiazines and [1,2]dithiolopyrroles. J Org Chem 69:3672

    Article  CAS  Google Scholar 

  • Buckle DR, Cantello BCC, Smith H, Spicer BA (1975) 4-Hydroxy-3-nitro-2-quinolones and related compounds as inhibitors of allergic reactions. J Med Chem 18:726–732

    Article  CAS  Google Scholar 

  • Cappelli A, Mohr GP, Gallelli A, Rizzo M, Anzini M, Vomero S, Mennuni L, Ferrari F, Makovec F, Menziani MC, De Benedetti PG, Giorgi G (2004) Design, synthesis, structural studies, biological evaluation, and computational simulations of novel potent AT1 angiotensin II receptor antagonists based on the 4-phenylquinoline structure. J Med Chem 47:2574–2586

    Article  CAS  Google Scholar 

  • Chen Y-L, Chung C-H, Chen I-L, Chen P-H, Jeng H-Y (2002) Synthesis and cytotoxic activity evaluation of indolo-, pyrrolo-, and benzofuro-quinolin-2(1H)-ones and 6-anilinoindoloquinoline derivatives. Bioorg Med Chem 10:2705–2712

    Article  CAS  Google Scholar 

  • Ellis D, Kuhen KL, Anaclerio B, Wu B, Wolff K, Yin H, Bursulaya B, Caldwell J, Karanewsky D, He Y (2006) Design, synthesis, and biological evaluations of novel quinolones as HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett 16:4246–4251

    Article  CAS  Google Scholar 

  • Faber K, Stueckler H, Kappe T (1984) Non-steroidal antiinflammatory agents. 1. Synthesis of 4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl alkanoic acids by the wittig reaction of quinisatines. J Heterocycl Chem 21:1177–1181

    Article  CAS  Google Scholar 

  • Freeman GA, Andrews CW, Hopkins AL, Lowell GS, Schaller LT, Cowan JR, Gonzales SS, Koszalka GW, Hazen RJ, Boone LR, Ferris RG, Creech KL, Roberts GB, Short SA, Weaver K, Reynolds DJ, Milton J, Ren J, Stuart DI, Stammers DK, Chan JH (2004) Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 2. J Med 47:5923–5936

    CAS  Google Scholar 

  • Grundon MF (1998) Alkaloids, vol 32. Academic Press, London, pp 341–439

    Google Scholar 

  • Hassanin HM, Ibrahim MA, Gabr YA, Alnamer YA (2012) Synthesis and chemical reactivity of pyrano[3,2-c]quinolones. J Heterocycl Chem 49:1269–1289

    Article  CAS  Google Scholar 

  • Hopkins AL, Ren J, Milton J, Hazen RJ, Chan JH, Stuart DI, Stammers DK (2004) Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. J Med Chem 47:5912–5922

    Article  CAS  Google Scholar 

  • Kalita PK, Baruah B, Bhuyan PJ (2006) Synthesis of novel pyrano[2,3-b]quinolines from simple acetanilides via intramolecular 1,3-dipolar cycloaddition. Tetrahedron Lett 47:7779–7782

    Article  CAS  Google Scholar 

  • McCormick JL, McKee TC, Cardinella JH, Boyd MR (1996) HIV inhibitory natural products. 26. Quinoline alkaloids from Euodia roxburghiana. J Nat Prod 59:469–471

    Article  CAS  Google Scholar 

  • Mederski WWKR, Osswald M, Dorsch D, Christadler M, Schmitges C-J, Wilm C (1997) 1,4-Diaryl 2-oxo-1,2-dihydro-quinoline-3-carboxylic acids as endothelin receptor antagonists. Bioorg Med Chem Lett 7:1883–1886

    Article  CAS  Google Scholar 

  • Michael JP (1998) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 15:595–606

    Article  CAS  Google Scholar 

  • Mohtat B, Nahavandian S, Azar ZN, Djahaniani HZ (2011) Triphenylphosphine-promoted C-vinylation of 4-hydroxyquinolines. Naturforsch 66B:700–704

    Article  Google Scholar 

  • Moshapo PT, Sokamisa M, Mmutlane EM, Mampa RM, Kinfe HH (2016) A convenient domino Ferrier rearrangement-intramolecular cyclization for the synthesis of novel benzopyran-fused pyranoquinolines. Org Biomol Chem 14:5627–5638

    Article  CAS  Google Scholar 

  • Müller TJJ (2014) In Multicomponent reactions 2. Reaction involving an β-unsaturated carbonyl compound as electrophilic component, cycloadditions, and Born-, Silicon-, Free radical-, and Metal-Reactions. Georg-Thieme, Verlag

  • Nair V, Vinod AU, Ramesh R, Menon RS, Varma L, Mathew S, Chiaroni A (2002) An efficient multicomponent reaction involving the interception of the zwitterionic intermediate between DMAD and isocyanides with some active methylene compounds. Heterocycles 58:147–151

    Article  CAS  Google Scholar 

  • Nair V, Devipriya S, Suresh E (2008) A novel three-component reaction involving quinolone, dimethyl acetylenedicarboxylate, and C-H acids leading to the formation of pyrroloquinoline derivatives. Synthesis 2008:1065–1068. doi:10.1055/s-2008-1032128

  • Nicolaides DN, Litinas KE, Psaroulis I, Makri A, Adamopoulos S (2011) Reactions between 4-hydroxycoumarins or 4-hydroxy-1-methylquinoline and DMAD in the presence of phosphites. Synthesis of (chromen-3-yl)- and (quinolin-3-yl)-(dialkoxyphosphoryl)succinates. Phosp Sulfur Silicon Relat Elem 186:2104–2111

    Article  CAS  Google Scholar 

  • Rad-Moghadam K, Valadi AK, Alipour A (2014) LiBF4 integrated into [BMIm]BF4: an ionic-liquid metal composite and homogeneous catalyst for efficient synthesis of pyran-annulated heterocycles. Appl Organomet Chem 28:146–150

    Article  CAS  Google Scholar 

  • Ramesh M, Mohan PS, Shanmugam P (1984) A convenient synthesis of flindersine, atanine and their analogues. Tetrahedron 40:4041–4049

    Article  CAS  Google Scholar 

  • Rao VS, Darbarwar M (1988) One pot synthesis of 7-[1, 2-dihydro-4-hydroxy-1-methyl/phenyl-2-OXO-3-Quinolinyl]-5, 7-dihydro-5-methyl/phenyl-6H-[1]-benzo pyrano [3, 2-c] quinolin-6-ones. Synth Commun 18:2267–2272

    Article  CAS  Google Scholar 

  • Rechac VL, Cirujano FG, Corma A, Llabrés XFX (2016) Diastereoselective synthesis of pyranoquinolines on zirconium-containing UiO-66 metal–organic frameworks. Eur J Inorg Chem 2016:4512–4516. doi:10.1002/ejic.201600372

  • Sekar M, Rajendra PKJ (1988) Quinoline alkaloids: synthesis of pyrano[2,3-b]quinolines, haplofoline, lunacrine, and demethoxylunacrine. J Nat Prod 61:294–296

    Article  Google Scholar 

  • Steiner MK, Perston IR (2008) Optimizing endothelin receptor antagonist use in the management of pulmonary arterial hypertension. Vasc Health Risk Manag 4(5):943–952

    CAS  Google Scholar 

  • Tzeng CC, Lee KH, Wang TC, Han CH, Chen YL (2000) Pharm Res 17:715–719

    Article  CAS  Google Scholar 

  • Yadav JS, Reddy BVS, Rao RS, Kumar SK, Kunwar AC (2002) InCl3-Catalyzed hetero-Diels–Alder reaction: an expeditious synthesis of pyranoquinolines. Tetrahedron 58:7891–7896

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The NMR spectrometer at Florida Institute of Technology was purchased with assistance from the National Science Foundation (CHE 03-42251), USA.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Minia University, 61519, El-Minia, Egypt

    Essmat M. El-Sheref, Ashraf A. Aly, Aboul-Fetouh E. Mourad & Momtaz E. M. Bakheet

  2. Chemistry Department, Florida Institute of Technology, 150 W University Blvd., Melbourne, FL, 32901, USA

    Alan B. Brown

  3. Institute of Organic Chemistry, Karlsruhe Institute of Technology, 76131, Karlsruhe, Germany

    Stefan Bräse

Authors
  1. Essmat M. El-Sheref
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ashraf A. Aly
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aboul-Fetouh E. Mourad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alan B. Brown
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Stefan Bräse
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Momtaz E. M. Bakheet
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ashraf A. Aly.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

El-Sheref, E.M., Aly, A.A., Mourad, AF.E. et al. Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates. Chem. Pap. 72, 181–190 (2018). https://doi.org/10.1007/s11696-017-0269-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-017-0269-6

Keywords

Search

Navigation