Efficient one-pot synthesis of benzopyranobenzopyrans and naphthopyranobenzopyrans by domino aldol-type reaction/hetero Diels-Alder reaction of resorcinols and naphthols

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 101-108

  Lee, Yong Rok ^a   Kim, Yun Mi ^a   Kim, Sung Hong ^b  

^a Yeungnam University   (South Korea)

^b Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

Aldol type reaction; Benzopyranobenzopyrans; Hetero Diels Alder reaction; Naphthols; Naphthopyranobenzopyrans; Resorcinols

Indexed keywords

ACETOACETIC ACID; BENZALDEHYDE DERIVATIVE; BENZOPYRANOBENZOPYRAN DERIVATIVE; CARBON; ETHER DERIVATIVE; ETHYLENEDIAMINE; NAPHTHOL DERIVATIVE; NAPHTHOPYRANOBENOPYRAN DERIVATIVE; PYRAN DERIVATIVE; RESORCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALNUS;

EID: 56949085268     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.101     Document Type: Article

References (73)

1. Deligny M., Carreaux F., Toupet L., and Carboni B. Adv. Synth. Catal. 345 (2003) 1215
2. Yadav J.S., Reddy B.V.S., Sadashiv K., and Padmavani B. Adv. Synth. Catal. 346 (2004) 607
3. Bolm C., Verrucci M., Simic O., and Hackenberger C.P.R. Adv. Synth. Catal. 347 (2005) 1696
4. Berkessel A., Ertürk E., and Laporte C. Adv. Synth. Catal. 348 (2006) 223
5. Aznar F., García A.-B., and Cabal M.-P. Adv. Synth. Catal. 348 (2006) 2443
6. Howard J.A.K., Ilyashenko G., Sparkes H.A., Whiting A., and Wright A.R. Adv. Synth. Catal. 350 (2008) 869
7. Povarov L.S. Russ. Chem. Rev. 36 (1967) 656
8. Larock R.C., Yang H., Pace P., Cacchi S., and Fabrizi G. Tetrahedron Lett. 39 (1998) 1885
9. Padwa A., Brodney M.A., Liu B., Satake K., and Wu T. J. Org. Chem. 64 (1999) 3595
10. Bunce R.A., Herron D.M., Johnson L.B., and Kotturi S.V. J. Org. Chem. 66 (2001) 2822
11. Zhang W., Jia X., Yang L., Zhao G., and Liu Z.-L. Tetrahedron Lett. 43 (2002) 9433
12. Baudelle R., Melnyk P., Deprez B., and Tartar A. Tetrahedron 54 (1998) 4125
13. Yamanaka M., Nishida A., and Nakagana M. Org. Lett. 2 (2000) 159
14. Bortolotti B., Leardini R., Nanni D., and Zanardi G. Tetrahedron 49 (1993) 10157
15. Grieco P.A., and Bahsas A. Tetrahedron Lett. 29 (1988) 5855
16. Ishitani H., and Kobayashi S. Tetrahedron Lett. 37 (1996) 7357
17. Sabitha G., Fatima N., Reddy E.V., and Yadav J.S. Adv. Synth. Catal. 347 (2005) 1353
18. Kim I., Kim S.G., Choi J., and Lee G.H. Tetrahedron 64 (2008) 664
19. Jimenez-Alonso S., Estevez-Braun A., Ravelo A.G., Zarate R., and Lopez M. Tetrahedron 63 (2007) 3066
20. Jayashankaran J., Manian R.D.R.S., and Raghunathan R. Tetrahedron Lett. 47 (2006) 2265
21. Yadav J.S., Reddy B.V.S., Naveenkumar V., Rao R.S., and Nagaiah K. Synthesis (2004) 1783
22. Yadav J.S., Reddy B.V.S., Narsimhaswamy D., Lakshmi P.N., Narsimulu K., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 45 (2004) 3493
23. Manikandan S., Shanmugasundaram M., and Raghunathan R. Tetrahedron 58 (2002) 8957
24. Tietze L.F. Chem. Rev. 96 (1996) 115
25. Tietze L.F., Ott C., Gerke K., and Buback M. Angew. Chem., Int. Ed. Engl. 32 (1993) 1485
26. Tietze L.F., and Steinmetz A. Angew. Chem., Int. Ed. 35 (1996) 651
27. Tietze L.F., Beifuss U., Lo{combining double acute accent}ko{combining double acute accent}s M., Rischer M., Go{combining double acute accent}hrt A., Scheldrick G.M., and Goehrt A. Angew. Chem., Int. Ed. Engl. 29 (1990) 527
28. Tietze L.F., Kettschau G., Gewert J.A., and Schuffenhauer A. Curr. Org. Chem. 2 (1998) 19
29. Tietze L.F., and Zhou Y. Angew. Chem., Int. Ed. 38 (1999) 2045
30. Davis M., and Pettett M. Aust. J. Chem. 32 (1979) 369
31. Rustaiyan A., Nazarians L., and Bohlmann F. Phytochemistry 19 (1980) 1254
32. Kamperdick C., Van N.H., Sung T.V., and Adam G. Phytochemistry 45 (1997) 1049
33. Cambie R.C., Pan Y.J., and Bowden B.F. Biochem. Syst. Ecol. 24 (1996) 461
34. Muyard F., Bissoue A.N., Bevalot F., Tillequin F., Cabalion P., and Vaquette J. Phytochemistry 42 (1996) 1175
35. Costa S.M.O., Lemos T.L.G., Pessoa O.D.L., Pessoa C., Montenegro R., and Braz-Filho R. J. Nat. Prod. 64 (2001) 792
36. Singh R., Geetanjali, and Chauhan S.M.S. Chem. Biodivers. 1 (2004) 1241
37. McKee T., Fuller R.W., Covington C.D., Cardellina II J.H., Gulakowski R.J., Krepps B.L., McMahon J.B., and Boyd M.R. J. Nat. Prod. 59 (1996) 754
38. Galinis D.L., Fuller R.W., McKee T.C., Cardellina II J.H., Gulakowski R.J., McMahon J.B., and Boyd M.R. J. Med. Chem. 39 (1996) 4507
39. Cardellina J.H., Bokesch H.R., McKee T.C., and Boyd M.R. Bioorg. Med. Chem. Lett. 5 (1995) 1011
40. Chanh P.H., Koffi Y., and Chanh A.P. Planta Med. 4 (1988) 294
41. Nakamura T., Okayama E., Yamazaki M., Satake M., Nishibe S., and Deyama T. Chem. Pharm. Bull. 45 (1997) 499
42. Crano J.C., kwak W.S., and Welch C.N. In: Ardle C.B. (Ed). Applied Photochromic Polymer Systems (1994), Chapman and Hall, New York, NY
43. Crano J.C., Flood T., Knowles D., Kumar A., and Van Germert B. Pure Appl. Chem. 68 (1996) 1395
44. Maltman, W. R., Threlfall, I. M. U.S. Patent 4,851,471, 1989;
45. Delaire J.A., and Nakatami K. Chem. Rev. 100 (2000) 1871
46. Irié M. Chem. Rev. 100 (2000) 1685
47. Berkovic G., Krongauz V., and Weiss V. Chem. Rev. 100 (2000) 1741
48. Kawata S., and Kawata Y. Chem. Rev. 100 (2000) 1777
49. Wilner I., and Rubin S. Angew. Chem., Int. Ed. 35 (1996) 367
50. Pieroni O., Fissi A., and Popova G. Prog. Polym. Sci. 23 (1998) 81
51. Bolm C., Rantanen T., Schiffers I., and Zani L. Angew. Chem., Int. Ed. 44 (2005) 1758
52. Berrisford D.J., Bolm C., and Sharpless K.B. Angew. Chem., Int. Ed. Engl. 34 (1995) 1059
53. Saito S., Nakadai M., and Yamamoto H. Synlett (2001) 1245
54. Saito S., and Yamamoto H. Acc. Chem. Res. 37 (2004) 570
55. Lee Y.R., Choi J.H., and Yoon S.H. Tetrahedron Lett. 46 (2005) 7539
56. Lee Y.R., Lee W.K., Noh S.K., and Lyoo W.S. Synthesis (2006) 853
57. Lee Y.R., and Kim D.H. Synthesis (2006) 603
58. Lee Y.R., and Kim J.H. Synlett (2007) 2232
59. Wang X., and Lee Y.R. Tetrahedron Lett. 48 (2007) 6275
60. Wang X., and Lee Y.R. Synthesis (2007) 3044
61. Lee Y.R., and Xia L. Synthesis (2007) 3240
62. Lee Y.R., Li X., and Kim J.H. J. Org. Chem. 73 (2008) 4313
63. Lee Y.R., and Xia L. Tetrahedron Lett. 49 (2008) 3283
64. Xia L., and Lee Y.R. Synlett (2008) 1643
65. Lee Y.R., and Hung T.V. Tetrahedron 64 (2008) 7338
66. Shanmugasundaram M., Manikandan S., and Raghunathan R. Tetrahedron 58 (2002) 997
67. Tietze L.F., Geissler H., Fennen J., Brumby T., Brand S., and Schulz G. J. Org. Chem. 59 (1994) 182
68. Saimoto H., Yoshida K., Murakami T., Morimoto M., Sashiwa H., and Shigemasa Y. J. Org. Chem. 61 (1996) 6768
69. Lumb J.-P., and Trauner D. Org. Lett. 26 (2005) 5865
70. Hoffmann R.W. Chem. Rev. 89 (1989) 1841
71. Tietze L.F., Beifuss U., Ruther M., Ru{combining double acute accent}hlmann A., Antel J., and Sheldrick G.M. Angew. Chem., Int. Ed. Engl. 27 (1988) 1186
72. Tietze L.F., Brumby T., Pretor M., and Remberg G. J. Org. Chem. 53 (1988) 810
73. Reaction of 4-hydroxy-1-methyl-2-quinolone (35) with 3 in the presence of EDDA/TEA gave product 36 (59%) as a sole compound.{A figure is presented}{A figure is presented}