Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5515-5519

  Clarke, David S ^a   Gabbutt, Christopher D ^a   Hepworth, John D ^b   Heron, B Mark ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b James Robinson Ltd   (United Kingdom)

Author keywords

Chroman 4 ones; Chromones; Conjugate reduction; Flavones; Rearrangement

Indexed keywords

4 CHROMANONE DERIVATIVE; ACID ANHYDRIDE; BENZENE DERIVATIVE; CHROMONE DERIVATIVE; FLAVONE DERIVATIVE; METHANE; PYRAN DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 22144433401     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.058     Document Type: Article

References (34)

1. G.P. Ellis G.P. Ellis Chromenes, Chromanones and Chromones 1977 Wiley-Interscience New York 581 631
2. H.-J. Kabbe, and A. Widdig Angew. Chem., Int. Ed. Engl. 21 1982 247 256
3. C.D. Gabbutt, and J.D. Hepworth Tetrahedron Lett. 26 1985 1879 1882
4. C.D. Gabbutt, J.D. Hepworth, M.W.J. Urquhart, and L.M. Vazquez de Miguel J. Chem. Soc., Perkin Trans. 1 1998 1547 1553
5. C.D. Gabbutt, J.D. Hepworth, and B.M. Heron J. Chem. Soc., Perkin Trans. 1 2000 2930 2938
6. W.M. Abdou, M.D. Khidre, and M.R. Mahran Phosphorus, Sulfur 61 1991 83 90
7. A. Sandulache, A.M.S. Silva, D.C.G.A. Pinto, L.M.P.M. Almeida, and J.A.S. Cavaleiro New J. Chem. 27 2003 1592 1598
8. 3-(2-Phenylstyryl)chromone is more efficiently obtained from hydrolysis of the cycloadduct of 3-formylchromone and diphenylketene, F. Eiden, and I. Breugst Chem. Ber. 112 1979 1791 1807
9. P. Langer, and E. Holtz Synlett 2003 402 404
10. C.K. Ghosh, N. Tewari, and A. Bhattacharyya Synthesis 1984 614 615
11. A. Nohara, H. Kuriki, T. Saijo, K. Ukawa, T. Murata, M. Kanno, and Y. Sanno J. Med. Chem. 18 1975 34 37
12. condensations of 3-formylchromone with acetylacetone and ethyl acetoacetate have also been described, W.D. Jones, and W.L. Albrecht J. Org. Chem. 41 1976 706 707
13. A. Nohara, H. Kuriki, T. Saijo, H. Sugihara, M. Kanno, and Y. Sanno J. Med. Chem. 20 1977 141 145
14. S.G. Davies, B.E. Mobbs, and C.J. Goodwin J. Chem. Soc., Perkin Trans. 1 1987 2597 2604
15. V.L.M. Silva, A.M.S. Silva, D.C.G.A. Pinto, J.A.S. Cavaleiro, and T. Patonay Synlett 2004 2717 2720
16. V. Lokshin, A. Heynderickx, A. Samat, G. Pepé, and R. Guglielmetti Tetrahedron Lett. 40 1999 6761 6764
17. T.S. Wheeler Org. Syn., Coll. Vol. 4 1963 479
18. K.R. Huffman, M. Burger, J.A. Henderson Jr., M. Loy, and E.F. Ullman J. Org. Chem. 34 1969 2407 2414
19. Huffman, K. R.; Ullman, E. F. US Patent 1969, 3 444 212; Chem. Abstr. 1969, 71, 38807.
20. W. Baker, J.B. Harborne, and W.D. Ollis J. Chem. Soc. 1952 1294 1302
21. We have previously noted the efficacy with which conjugate reductions of activated chromones proceed under these conditions: C.D. Gabbutt, J.D. Hepworth, M.W.J. Urquhart, and L.M. Vazquez de Miguel J. Chem. Soc., Perkin Trans. 1 1997 1819 1824
22. 2CuLi to 3-acylchromones; S.T. Saengchantara, and T.W. Wallace Tetrahedron 46 1994 3029 3036
23. 4) Other 3-alkenylchromones were prepared similarly. Yields (%) 6a (70), 6c (87) 6d (95), 6e (62) 6h (30), 6i (40), 6j (66), 6k (60);
24. + requires 277.1221.
25. 2b and 3
26. 3 as catalyst), compounds 7c (57%) and 7d (63%) could only be obtained satisfactorily by the DBU procedure;
27. G.A. Kraus, B.S. Fulton, and S.H. Woo J. Org. Chem. 49 1984 3212 3214
28. 3), 2.40-2.65 (2H, m, H-5), 4.57-4.72 (1H, m, H-6), 7.10-7.61 (4H, m, Ar-H)
29. The only reported example of direct formation of a pyranone ring from 1,3-diketones 8 concerns the cycloaddition of pyrrolidinocycloalkenes to (E)-1-(2-hydroxyphenyl)-5-phenylpent-4-ene-1,3-dione 8a, which provides cycloalkeno[a]- and cycloalkeno[d]xanthones, R.M. Letcher, T.-Y. Yue, K.-F. Chiu, A.S. Kelkar, and K.-K. Cheung J. Chem. Soc., Perkin Trans. 1 1998 3267 3276
30. The cycloaddition chemistry of chromones has been reviewed, C.K. Ghosh, and C. Ghosh Indian J. Chem., Sect. B 36 1997 968 980
31. 3b and C.D. Gabbutt, J.D. Hepworth, B.M. Heron, and S.L. Pugh J. Chem. Soc., Perkin Trans. 1 2002 2799 2808
32. D.C.G.A. Pinto, A.M.S. Silva, L.M.P.M. Almeida, J.R. Carrillo, A. Díaz-Ortiz, A. de la Hoz, and J.A.S. Cavaleiro Synlett 2003 1415 1418
33. 3, 250 MHz) 3.99 (3H, s, OMe), 7.24-7.47 (3H, m, Ar-H), 7.62-7.77 (3H, m, Ar-H), 8.26 (1H, d, J = 8.7 Hz, H-5), 8.37 (1H, dd, J = 7.8, 1.5 Hz, H-8), 8.59 (1H, d, J = 8.7 Hz, H-6)
34. 3, 250 MHz) 1.63 (3H, d, J = 7.4 Hz, 10-Me), 3.91 (3H, s, OMe), 4.03 (1H, d, J = 7.4 Hz, H-10), 7.01 (1H, dd, J = 8.4, 2.2 Hz, H-7), 7.12 (1H, d, J = 2.2 Hz, H-9), 7.65 (1H, td, J = 8.4, 2.2 Hz, H-4), 7.73-7.74 (2H, m, H-2, H-3), 7.75 (1H, d, J = 8.4 Hz, H-6), 8.34 (1H, dd, J = 8.4, 2.2 Hz, H-1).