Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)
Full text:
download
(downloads: 134)
Language: 
Russian
Heading: 
Chemistry
Article type: 
Article
UDC: 
547.828.2+547.853.3
DOI: 
10.18500/1816-9775-2019-19-3-284-288

2-amino-3-formilchromen-4-one as “Connection-platform” in the Synthesis of Hybrid Systems under the Action of N-Nucleophiles

Autors: 
Ivanova Aleksandra L., Saratov State University
Kanevskaya Irina V., Saratov State University
Ibragimova Diana K., Saratov State University
Fedotova О. V., Saratov State University
Abstract: 

Показано, что 4H-хроменоны, функционализированные альдегидной группой в положении С3, способны образовывать гибридные системы, имеющие в своей структуре помимо хроменонового пиридиновый, пиримидиновый циклы. Кислая среда способствует раскрытию ?-лактонного фрагмента. Показана возможность дезактивации альдегидной группы с последующим деформилированием. 

Key words: 
4H-chromenones
hybrid systems
?-lactones
2-amino4-oxo-4H-chromen-3-carbaldehyde
N-nucleophiles
Reference: 
  1. Miao H., Yang Z. Regiospecific carbonylative annula- tion of iodophenol acetates and acetylenes to construct the flavones by a new catalyst of palladium?thiourea? dppp complex // Organic Letters. 2000. Vol.  2, № 12.   P. 1765–1768.DOI: https://doi.org/10.1021/ol000087t
  2. Lyckander I. M. Lipophilic flavonoids from Orthosiphon spicatus as in-hibitors of 15-lipoxygenase // Acta Pharma- ceutica Nordica. 1992. Vol. 4, № 3. P. 159–166.
  3. Malterud K. E. Inhibitors of 15-lipoxygenase from orange peel // Journal of Agricultural and Food Chemistry. 2000. Vol. 48, № 11. P. 5576–5580.DOI: https://doi.org/10.1021/jf000613v
  4. Denis L., Morton M. S., Griffiths K. Diet and its preven- tive role in prostatic disease // European Urology. 1999. Vol. 35, № 5–6. P. 377–387.
  5. Gabor M. Anti-inflammatory and anti-allergic properties of flavonoids // Progress in Clinical and Biological Research. 1986. Vol. 213. P. 471.
  6. Desideri N., Mastromarino P., Conti C. Synthesis and evaluation of antirhinovirus activity of 3-hydroxy and 3-methoxy 2-styrylchromones // Antiviral Chemistry and Chemotherapy. 2003. Vol. 14, № 4. P. 195–203.
  7. Marder M. Detection of benzodiazepine receptor ligands in small libraries of flavone derivatives synthesized by solution phase combinatorial chemistry // Biochemi- cal and Biophysical Research Communications. 1998. Vol. 249, № 2. P. 481–485.DOI: https://doi.org/10.1006/bbrc.1998.9146
  8. Gomes A. Synthesis and antioxidant properties of new chromone derivatives // Bioorganic & Medicinal Chem- istry. 2009. Vol. 17, № 20. P. 7218–7226.DOI: https://doi.org/10.1016/j. bmc.2009.08.056 
  9. Saloutin V. I. Novel fluorinated chromones // Journal of Fluorine Chemistry. 1993. Vol. 65, № 1–2. P. 37–41.DOI: https://doi.org/10.1016/S0022-1139(00)80470-4
  10. Ibrahim M. A., El-Mahdy K. M. Synthesis and antimi- crobial activity of some new heterocyclic Schiff bases derived from 2-amino-3-formylchromone // Phosphorus,Sulfur, and Silicon. 2009. Vol. 184, № 11. P. 2945–2958.DOI: https://doi.org/10.1080/10426500802625594
  11. Fitton A. O. Conversion of 3-formylchromones into pyrrole and thiophene derivatives // Synthesis. 1977. Vol. 1977, № 2. P. 133–135.
  12. Achaiah G., Jayamma Y., Reddy V. M. Synthesis and biological evaluation of 2-[3-aryl-4 (3H)-quinazolinon- 2yl] pyrrolino [5, 4-b] 2, 3-dihydro-4H-[1]-benzopy- ran-4-ones // Ind. J.  Heterocycl.  Chem.  1991. Vol.  1. P. 39–42.