Abstract
Condensation of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selected heteroarylamines in acetonitrile containing a catalytic amount of triethylamine, followed by intramolecular cyclization, gave the new coumarin derivatives with yields ranging from 43 % to 78 %. The novel compounds were subjected to acid hydrolysis giving the corresponding oxo derivatives in 66–70 % yield. The structural assignments of the synthesized compounds were based on elemental, IR, 1H and 13C NMR analyses.
[1] Coumarins: Biology, Applications and Mode of Action (O’Kennedy, R. and Thornes, R. D., Editors). Wiley, Chichester, 1997. Search in Google Scholar
[2] Soine, T. O., J. Pharm. Sci. 53, 231 (1964). http://dx.doi.org/10.1002/jps.260053030210.1002/jps.2600530302Search in Google Scholar PubMed
[3] Marcu, M. G., Schulte, T. W., and Neckers, L., J. Natl. Cancer Inst. 92, 242 (2000). http://dx.doi.org/10.1093/jnci/92.3.24210.1093/jnci/92.3.242Search in Google Scholar PubMed
[4] Oliver, G. F. and Winkelmann, R. K., Drugs 45, 56 (1993). 10.2165/00003495-199345010-00006Search in Google Scholar PubMed
[5] Radulovic, N., Stojanovic, G., Vukicevic, R., Dekic, V., Dekic, B., and Palic, R., Monatsh. Chem. 137, 1477 (2006). http://dx.doi.org/10.1007/s00706-006-0537-610.1007/s00706-006-0537-6Search in Google Scholar
[6] Anschutz, R., Ber. Dtsch. Chem. Ges. 36, 463 (1903). Search in Google Scholar
[7] Chechi, S., Pecori Vettori, L., and Mambagiotti, M., Gazz. Chim. Ital. 98, 1448 (1968). Search in Google Scholar
[8] Kaljaj, V., Trkovnik, M., and Stefanovic-Kaljaj, L., J. Serb. Chem. Soc. 52, 183 (1987). Search in Google Scholar
[9] Kaljaj, L., Kaljaj, V., Dekic, S., Sokolic, Lj., and Palic, R., J. Serb. Chem. Soc. 61, 419 (1996). Search in Google Scholar
[10] Govori, S., Kaljaj, V., Rapic, V., Kaljaj, L., and Dakovic, S., Heterocycl. Commun. 8, 129 (2002). Search in Google Scholar
[11] Stefanovic-Kaljaj, L., Kaljaj, V., and Trkovnik, M., J. Serb. Chem. Soc. 54, 169 (1989). Search in Google Scholar
© 2007 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- A review of methods for synthesis of nanostructured metals with emphasis on iron compounds
- Effect of selenium oxidation state on cadmium translocation in chamomile plants
- Optimization of ammonium nitrate concentration in single-stage continuous cultures of Aspergillus niger with biomass retention
- Behaviour of inorganic constituents of municipal sewage sludge during fluidized-bed combustion
- Profile distribution of As(III) and As(V) species in soil and groundwater in Bozanta area
- Structure of cyano-bridged Eu(III)—Co(III) bimetallic assembly and its application to photophysical verification of photomagnetic phenomenon
- Synthesis and characterization of oligo-4-[(pyridin-3-ylimino)methyl]phenol
- Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
- Improved DPPH determination for antioxidant activity spectrophotometric assay
- Notes on notation of sodium oxofluoroaluminate anions
- Determination of the enthalpy of fusion of Na3FeF6
- Controlled solvothermal synthesis of PbS quasi-nanorods by calix[4]arene
- Palladium-catalyzed heck and suzuki coupling in glycerol
- Synthesis of new condensed and cyclized coumarin derivatives
- M. Hartman, O. Trnka, and M. Pohořelý: Fluidization behavior of oil-contaminated sand
Articles in the same Issue
- A review of methods for synthesis of nanostructured metals with emphasis on iron compounds
- Effect of selenium oxidation state on cadmium translocation in chamomile plants
- Optimization of ammonium nitrate concentration in single-stage continuous cultures of Aspergillus niger with biomass retention
- Behaviour of inorganic constituents of municipal sewage sludge during fluidized-bed combustion
- Profile distribution of As(III) and As(V) species in soil and groundwater in Bozanta area
- Structure of cyano-bridged Eu(III)—Co(III) bimetallic assembly and its application to photophysical verification of photomagnetic phenomenon
- Synthesis and characterization of oligo-4-[(pyridin-3-ylimino)methyl]phenol
- Relationship between physicochemical properties, lipophilicity parameters, and local anesthetic activity of dibasic esters of phenylcarbamic acid
- Improved DPPH determination for antioxidant activity spectrophotometric assay
- Notes on notation of sodium oxofluoroaluminate anions
- Determination of the enthalpy of fusion of Na3FeF6
- Controlled solvothermal synthesis of PbS quasi-nanorods by calix[4]arene
- Palladium-catalyzed heck and suzuki coupling in glycerol
- Synthesis of new condensed and cyclized coumarin derivatives
- M. Hartman, O. Trnka, and M. Pohořelý: Fluidization behavior of oil-contaminated sand