Synthesis of the novel conjugated ω,ω′-diaryl/heteroaryl hexatriene system with the central double bond in a heteroaromatic ring: photochemical transformations of 2,3-divinylfuran derivatives

Tetrahedron

Volumn 62, Issue 31, 2006, Pages 7396-7407

  Škorić, Irena ^a   Flegar, Ivana ^a   Marinić, Željko ^b   Šindler Kulyk, Marija ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Oxygen heterocycles; Pericyclic reaction; Photochemistry; Rearrangement; Synthesis

Indexed keywords

FURAN DERIVATIVE; PHENANTHRENE DERIVATIVE; POLYCYCLIC HYDROCARBON; STILBENE;

ARTICLE; CHEMICAL BOND; CONJUGATION; CYCLOADDITION; IRRADIATION; ISOMERIZATION; MOLECULE; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33745187584     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.034     Document Type: Article

References (57)

1. Šindler-Kulyk M., Špoljarić L., and Marinić Z. Heterocycles 29 (1989) 679-682
2. Šindler-Kulyk M., Kragol G., Piantanida I., Tomšić S., Vujković Cvijin I., Marinić Z., and Metelko B. Croat. Chem. Acta 69 (1996) 1593-1602
3. Vujković Cvijin I., Marinić Z., and Šindler-Kulyk M. Spectrosc. Lett. 31 (1998) 989-1000
4. Šindler-Kulyk M., Škorić I., Tomšić S., Marinić Z., and Mrvoš-Sermek D. Heterocycles 51 (1999) 1355-1369
5. Škorić I., Marinić Z., and Šindler-Kulyk M. Heterocycles 53 (2000) 55-68
6. Škorić I., Basarić N., Marinić Z., and Šindler-Kulyk M. Heterocycles 55 (2001) 1889-1896
7. Škorić I., Hutinec A., Marinić Z., and Šindler-Kulyk M. ARKIVOC (2003) 87-97
8. Škorić I., Marinić Z., and Šindler-Kulyk M. Croat. Chem. Acta 77 (2004) 161-166
9. Škorić I., Basarić N., Marinić Z., Višnjevac A., Kojić-Prodić B., and Šindler-Kulyk M. Chem.-Eur. J. 11 (2005) 543-551
10. Šindler-Kulyk M., Tomšić S., Marinić Z., and Metelko B. Recl. Trav. Chim. Pays-Bas 114 (1995) 476-479
11. Basarić N., Tomšić S., Marinić Z., and Šindler-Kulyk M. Tetrahedron 56 (2000) 1587-1593
12. Basarić N., Marinić Z., and Šindler-Kulyk M. Tetrahedron Lett. 42 (2001) 3641-3643
13. Basarić N., Marinić Z., Višnjevac A., Kojić-Prodić B., Griesbeck A.G., and Šindler-Kulyk M. Photochem. Photobiol. Sci. 1 (2002) 1017-1023
14. Rademacher P., Basarić N., Kowski K., and Šindler-Kulyk M. Eur. J. Org. Chem. (2002) 551-556
15. Basarić N., Marinić Z., and Šindler-Kulyk M. J. Org. Chem. 68 (2003) 7524-7527
16. Basarić N., Marinić Z., and Šindler-Kulyk M. Tetrahedron Lett. 44 (2003) 7337-7340
17. Butković K., Basarić N., Lovreković K., Marinić Z., Višnjevac A., Kojić-Prodić B., and Šindler-Kulyk M. Tetrahedron Lett. 45 (2004) 9057-9060
18. Butković K., Marinić Z., and Šindler-Kulyk M. Magn. Reson. Chem. 42 (2004) 1053-1055
19. Šindler-Kulyk M., and Laarhoven W.H. J. Am. Chem. Soc. 98 (1976) 1052-1053
20. Šindler-Kulyk M., and Laarhoven W.H. J. Am. Chem. Soc. 100 (1978) 3819-3830
21. Šindler-Kulyk M., and Laarhoven W.H. Recl. Trav. Chim. Pays-Bas 98 (1979) 187-191
22. Šindler-Kulyk M., and Laarhoven W.H. Recl. Trav. Chim. Pays-Bas 98 (1979) 452-459
23. Op den Brouw P.M., and Laarhoven W.H. J. Org. Chem. 47 (1982) 1546-1555
24. Op den Brouw P.M., and Laarhoven W.H. Recl. Trav. Chim. Pays-Bas 101 (1982) 58-67
25. Op den Brouw P.M., and Laarhoven W.H. J. Chem. Soc., Perkin Trans. 2 (1982) 795-799
26. Op den Brouw P.M., and Laarhoven W.H. J. Chem. Soc., Perkin Trans. 2 (1983) 1015-1020
27. Op den Brouw P.M., de Zeeuw P., and Laarhoven W.H. J. Photochem. 27 (1984) 327-341
28. Laarhoven W.H. Recl. Trav. Chim. Pays-Bas 102 (1983) 241-254
29. Laarhoven W.H. Pure Appl. Chem. 56 (1984) 1225-1240
30. Laarhoven W.H., and Cuppen Th.J.H.M. J. Photochem. 32 (1986) 105-118
31. Tol A.J.W., and Laarhoven W.H. J. Org. Chem. 51 (1986) 1663-1668
32. Song Z.Z., and Wong H.N.C. J. Chin. Chem. Soc. 42 (1995) 673-679
33. Song Z.Z., Wong H.N.C., and Yang Y. Pure Appl. Chem. 68 (1996) 723-726
34. Karminski-Zamola G., Dogan J., Bajić M., Blažević J., and Malešević M. Heterocycles 38 (1994) 759-767
35. Pennanen S.I. J. Heterocycl. Chem. 14 (1977) 745-748
36. Yokoyama Y., Takashima M., Higaki Ch., Shidori K., Moriguchi Sh., Ando Ch., and Murakami Y. Heterocycles 36 (1993) 1739-1742
37. Jones R.R., Brown J.M., and Sondheimer F. Tetrahedron Lett. 47 (1975) 4183-4186
38. Shibuya H., Yamamoto Y., Miura I., and Kitagawa I. Heterocycles 17 (1982) 215-218
39. Vuligonda V., Garst M.E., and Chandraratna A.S. Bioorg. Med. Chem. Lett. 9 (1999) 589-594
40. Hiroyasu, T.; Harumasa, Y.; Masayuki, M.; Tadashi, S. Patent No. JP 03,135,570, 1991, 10 pages, Patent written in Japanese.
41. Buckle, D.R. Eur. Pat. Appl. Patent No. EP 194,093, 1986, 58 pages.
42. Shiro, I.; Takamasa, I.; Mutsumi, K.; Hidemi, I. Patent No. JP 09,059,207, 1997, 19 pages, Patent written in Japanese.
43. For a review of hexatriene photochemistry see:. Fonken G.J. In: Chapman O.L. (Ed). Organic Photochemistry Vol. 1 (1967), Marcel Dekker, New York, NY 222
44. Dauben W.G., Kellog M.S., Seeman J.I., Vietmeyer N.D., and Wendschuh P.H. Pure Appl. Chem. 33 (1973) 197
45. No attempt was made to synthesize the other constitutional isomers.
46. Padwa A. In: de Mayo P. (Ed). Rearrangement in Ground and Excited States Vol. 3 (1980), Academic, New York, NY
47. D'Auria M. Heterocycles 50 (1999) 1115-1136
48. D'Auria M. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry: Photochemical Isomerization of Pentaatomic Heterocycles (2001), Academic, San Diego, CA 41-88
49. Mallory F.B., Wood C.S., and Gordon J.T. J. Am. Chem. Soc. 86 (1964) 3094-3100
50. Zanetti J.E. J. Am. Chem. Soc. 49 (1927) 1065-1067
51. Cook M.J., and Forbes E.J. Tetrahedron 24 (1968) 4501-4508
52. Pelter A., and Siugaram B. J. Chem. Soc., Perkin Trans. 1 (1983) 1383-1386
53. Burness D.M. In: Rabjohn N. (Ed). Org. Syntheses Coll. Vol. 4 (1963) pp 628-630 and 649-652
54. Gronovitz S., and Michael V. Ark. Kemi 32 (1970) 283-294
55. 56,57
56. Seus E.J. J. Heterocycl. Chem. 2 (1965) 318-320
57. Van Der Looy J.F.A., Thys G.J.H., Dieltiens P.E.M., Schrijver D.D., Alsenoy Ch.V., and Geise H.J. Tetrahedron 53 (1997) 15069-15084