A facile route to phenyl, phenylsulfanyl and phenylselanyl substituted pyrano[3,2-c]chromenes

Tetrahedron

Volumn 66, Issue 6, 2010, Pages 1410-1419

  Lácová, Margita ^a   Gašparová, Renata ^b   Koiš, Pavol ^a   Boháč, Andrej ^a   El Shaaer, Hafez M ^c  

^a Faculty of Natural Sciences   (Slovakia)

^b UNIVERSITY OF SS CYRIL AND METHODIUS   (Slovakia)

^c Ain Shams University   (Egypt)

Author keywords

Acetic acids; Antineoplastic activity; Chromenes; Condensation; Microwave; Rearrangement

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL; ALDEHYDE DERIVATIVE; AMIDE; CHROMENE DERIVATIVE; WATER;

ARTICLE; CHEMICAL REACTION; HEATING; MICROWAVE IRRADIATION; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; WATER TREATMENT;

EID: 73649134691     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.057     Document Type: Article

References (49)

1. Nohara A., Ishiguro T., and Sanno Y. Tetrahedron 13 (1974) 1183-1186
2. Sabitha G. Aldrichimica Acta 29 (1996) 15-25
3. Ghosh C.K., Bandyopadhyay C., and Morin C. J. Chem. Soc., Perkin Trans. 1 (1983) 1989-1994
4. Ghosh C.K. Heterocycles 63 (2004) 2875-2898
5. Gašparová R., and Lácová M. Molecules 10 (2005) 937-960
6. Eicher T., and Hauptmann S. The Chemistry of Heterocycles (1995), Georg Thieme, Stuttgart, New York, NY
7. Edwards A.M., and Howell J.B.L. Clin. Experim. Allergy 30 (2000) 756-774
8. Ishar M.P.S., Singh G., Singh S., Sreenivasan K.K., and Singh G. Bioorg. Med. Chem. Lett. 16 (2006) 1366-1370
9. Liu J., Wu J., Zhao Y.X., Deng Y.Y., Mei W.L., and Dai H.F. Chin. Chem. Lett. 19 (2008) 934-936
10. Nawrot-Modranka J., Nawrot E., and Graczyk J. Eur. J. Med. Chem. 41 (2006) 1301-1309
11. El-Shaaer H.M., Foltínova P., Lácová M., Chovancová J., and Stankovičová H. Farmaco 53 (1998) 224-232
12. Gašparová R., Lácová M., El-Shaaer H.M., and Odlerová Z. Il Farmaco 52 (1997) 251-253
13. Mao P.C.M., Mouscadet J.F., Leh H., Auclair C., and Hsu L.Y. Chem. Pharm. Bull. 50 (2002) 1634-1637
14. Kirkiacharian S., Thuy D.T., Sicsic S., Bakhchinian R., Kurkijan R., and Tonnaire T. Il Farmaco 57 (2002) 703-708
15. Sakai T., Katayama T., and Takeda A. J. Org. Chem. 46 (1981) 2924-2931
16. Fields E.K., Behrend S.J., Meyerson S., Winzenburg M.L., Ortega B.R., and Hall H.K. J. Org. Chem. 55 (1990) 5165-5170
17. Su H., Shirai K., and Kumamoto T. Bull. Chem. Soc. Jpn. 65 (1992) 2794-2799
18. Babin D., Demassey J., Demoute J.P., Dutheil P., Terrie I., and Tessier J. J. Org. Chem. 57 (1992) 584-589
19. Gaultier A., Roche D., Metin J., Carpy A., and Madesclaire M. J. Mol. Struct. 355 (1995) 177-184
20. Jovanovic B.Z., Misic-Vukovic M., Drmanic S.Z., and Canadi J.J. J. Mol. Struct. 410 (1997) 39-42
21. Wirth T. Angew. Chem. Int. Ed. 39 (2000) 3740-3749
22. Wirth T. Liebigs Ann. (1997) 2189-2196
23. Wirth T. Tetrahedron 55 (1999) 1-28
24. Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis (1986), Pergamon, Oxford
25. Burger K., Gold M., Neuhauser H., Rudolph M., and Hoess E. Synthesis (1992) 1145-1150
26. Burling F.T., and Goldenstein B.M. J. Am. Chem. Soc. 114 (1992) 2313-2320
27. In: Burk R.F. (Ed). Selenium in Biology and Human Health (1994), Springer, New York, NY
28. Nefedova T.V., Kubatiev A.A., Martynov A.V., Guseva S.A., Kazimirovskya V.B., Mirskova A.N., Novikova N.V., Lobanova E.G., Nepsha V.D., Moskvitina L.T., and Voronkov M.G. Khim. Pharm. Zh. 21 (1987) 1081-1084
29. Lácová M., Gašparová R., Loos D., Liptay T., and Pronayová N. Molecules 5 (2000) 167-178
30. Gašparová R., Lácová M., and Krutošíková A. Collect. Czech. Chem. Commun. 70 (2005) 2101-2111
31. Stankovičová H., Gašparová R., Lácová M., and Chovancová J. Collect. Czech. Chem. Commun. 62 (1997) 781-790
32. Stankovičová H., Gáplovský A., Lácová M., Chovancová J., and Puchala A.J. Heterocycl. Chem. 43 (2006) 843-848
33. Stankovičová H., Lácová M., Gáplovský A., Chovancová J., and Pronayová N. Tetrahedron 57 (2001) 3455-3464
34. Gáplovský A., Donovalová J., Lacová M., Mračnová R., and El-Shaaer H.M. J. Photochem. Photobiol., A 136 (2000) 61-65
35. El-Shaaer H.M., Perjessy A., Zahradník P., Lácová M., and Šusteková Z. Monatsh. Chem. 124 (1993) 539-548
36. Stankovičová H., Fabian W.M.F., and Lácová M. Molecules 1 (1997) 223-235
37. Morgan G.T., and Porritt W.H. J. Chem. Soc. Trans. 127 (1925) 1755-1759
38. Martynov A.V., Mirskova A.N., Kalikhman I.D., and Voronkov M.G. Zh. Org. Khim. 24 (1988) 509-518
39. Robinson C.N., Shaffer A.A., Slater C.D., and Gelbaum L.T. J. Org. Chem. 58 (1993) 3563-3567
40. Lucchetti J., and Krief A. Tetrahedron Lett. (1978) 2693-2696
41. Lácová M., Stankovičová H., Boháč A., and Kotzianová B. Tetrahedron 64 (2008) 9646-9653
42. Silva V.L.M., Silva A.M.S., Pinto D.C.G.A., Cavaleiro J.A.S., and Patonay T. Synlett (2004) 2717-2720
43. Chen Y.S., Khan M., Rao S.N., Krishnaiah M., and Raju K.V.N. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 52 (1996) 1847-1849
44. Krishnaiah M., Raju K.V.N., Lu I.L., Chen Y.S., and Rao S.N. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 51 (1995) 2429-2430
45. http://www.cancer.gov
46. patent aplication: Lácová,M.; Boháč, A. New type of antineoplastic compounds with pyrano[3,2-c]chromen-2(5H)-one skeleton and the process of their synthesis. PP5006-2006, 2010.
47. Zhong P., and Guo M.P. Synth. Commun. 31 (2001) 1507-1510
48. Clarembeau M., Cravador A., Dumont W., Hevesi L., Krief A., Lucchetti J., and Van Ende D. Tetrahedron 41 (1985) 4793-4812
49. Grant D.W., Wardell J.L., and James L. J. Organomet. Chem. 276 (1984) 161-166