PEG-400 as green reaction medium for Lewis acid-promoted cycloaddition reactions with isoeugenol and anethole

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3097-3100

  Kouznetsov, Vladimir V ^a   Merchan Arenas, Diego R ^a   Romero Bohórquez, Arnold R ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

2,3 Dihydrobenzofuran 5 ols; Benzoquinone; Imino Diels Alder reaction; Multi component reaction; Polyetilenglicol (PEG 400); Tetrahydroquinolines; trans Anethole; trans Isoeugenol

Indexed keywords

1,4 BENZOQUINONE; 2,4 DIARYL 1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; ANETHOLE; ANILINE; BENZALDEHYDE; ISOEUGENOL; LEWIS ACID; MACROGOL 400; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALNUS;

EID: 41649113901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.049     Document Type: Article

References (59)

1. Hayashi T., and Thomson T.H. Phytochemistry 14 (1975) 1085
2. Clive D.L.J., and Stoffman E.J.L. Chem. Commun. (2007) 2151
3. Hada S., Hattori M., Tezuka Y., Kikuchi T., and Namba T. Phytochemistry 27 (1988) 563
4. Jaquemond-Collet I., Hannedouche S., Fabre N., Fourasté I., and Moulis C. Phytochemistry 51 (1999) 1167
5. Hutchinson S.A., Luetjens H., and Scammells P.J. Bioorg. Med. Chem. Lett. 7 (1997) 3081
6. Hattori M., Yang X.W., Shu Y.Z., Kakiuchi N., Tezuka Y., Kikuchi T., and Namba T. Chem. Pharm. Bull. 36 (1988) 648
7. Kunstmann R., Lerch U., Gerhards H., Leven M., and Schacht U. J. Med. Chem. 27 (1984) 432
8. Griengl, H.; Foidl, G. U.S. Patent 4,256,764, 1981.
9. Houghton P.J., Woldermariam T.Z., Watanabe T., and Yates M. Planta Med. 65 (1999) 250
10. Jaquemond-Collet I., Benoit-Vical T., Mustofa V., Stanislas E., and Mallié M. Planta Med. 68 (2002) 68
11. For a recent review on imino Diels-Alder reactions, see:. Buonora P., Olsen J.-C., and Oh T. Tetrahedron 57 (2001) 6099
12. For recent examples of imino Diels-Alder reactions catalyzed by various Lewis or Brønsted acids, see:. Legros J., Crousse B., Qurévitch M., and Bonnet-Delpon D. Synlett (2006) 1899
13. Savitha G., and Perumal P.T. Tetrahedron Lett. 47 (2006) 3589
14. Akiyama T., Nakashima S., Yokota K., and Fuchibe K. Chem. Lett. 33 (2004) 922
15. Akiyama T., Morita H., and Fuchibe K. J. Am. Chem. Soc. 128 (2006) 13070
16. Sridharan V., Perumal P.T., Avendaño P.C., and Menéndez J.C. Org. Biomol. Chem. 5 (2007) 1351
17. For a recent review on three-component reactions, see:. Syamala M. Org. Prep. Proced. Int. 37 (2005) 103
18. For recent examples of three-component imino Diels-Alder reactions, see:. Demaude T., Knerr L., and Pasau P. J. Comb. Chem. 6 (2004) 768
19. Kobayashi S., and Nagayama S. J. Am. Chem. Soc. 118 (1996) 8977
20. Kiselyov A., Smith L., and Armstrong R. Tetrahedron 54 (1998) 5089
21. Kiselyov A., Smith L., Virgilio A., and Armstrong R. Tetrahedron 54 (1998) 7987
22. Crousse B., Bèguè J.-P., and Bonnet-Delpon D. Tetrahedron Lett. 39 (1998) 5765
23. Katritzky A., Rachwal B., and Rachwal S. J. Org. Chem. 60 (1995) 3993
24. Talukdar S., Chen C.-T., and Fang J.-M. J. Org. Chem. 65 (2000) 3148
25. Kametani T., Takeda H., Suzuki Y., and Honda T. Heterocycles 22 (1984) 275
26. Zhang W., Jia X., Yang L., and Liu Z.-L. Tetrahedron Lett. 43 (2002) 9433
27. Jia X., Lin H., Huo C., Zhang W., Lü J., Zhao G., and Liu Z.-L. Synlett (2003) 1707
28. Engler T.A., Combrink K.D., Letavic M.A., Lynch Jr. K.O., and Ray J.E. J. Org. Chem. 59 (1994) 6567
29. Engler T.A., Wei D., Letavic M.A., Combrink K.D., and Reddy J.P. J. Org. Chem. 59 (1994) 6588
30. Engler T.A., Chai W., and Lynch Jr. K.O. Tetrahedron Lett. 36 (1995) 7003
31. Engler T.A., and Iyengar R. J. Org. Chem. 63 (1998) 1929
32. Wang S., Gates B.D., and Swenton J.S. J. Org. Chem. 56 (1991) 1979
33. Juhász L., Kürti L., and Antus S. J. Nat. Prod. 63 (2000) 866
34. Wang E.-C., Wein Y.-S., and Kuo Y.-H. Tetrahedron Lett. 47 (2006) 9195
35. Ohara H., Kiyokane H., and Itoh T. Tetrahedron Lett. 43 (2002) 3041
36. Yadav J.S., Reddy B.V.S., and Kondaji G. Synthesis (2003) 1100
37. For recent reviews, see:. Beckman E.J. J. Supercrit. Fluids 28 (2004) 121
38. Jain N., Kumar A., Chauhan S., and Chauhan S.M.S. Tetrahedron 61 (2005) 1015
39. Chen J., Spear S.K., Huddleston J.G., and Rogers R.D. Green Chem. 7 (2005) 64
40. Andrade K.Z., and Alves L.M. Curr. Org. Chem. 9 (2005) 195
41. For recent examples of the use of PEG in organic synthesis, see:. Li J.-H., Liu W.-J., and Xie Y.-X. J. Org. Chem. 70 (2005) 5409
42. Chandrasekhar S., Shyamsunder T., Chandrashekar G., and Narsihmulu C. Synlett (2004) 522
43. Zhang Z.-H., Yin L., Wang Y.-M., Liu J.-Y., and Li Y. Green Chem. 6 (2004) 563
44. Smith C.B., Raston C.L., and Sobolev A.N. Green Chem. 7 (2005) 650
45. Van den Ancker T.R.G., Cave W.V., and Raston C.L. Green Chem. 8 (2006) 50
46. Jain S.L., Singhal S., and Sain B. Green Chem. 9 (2007) 740
47. Cao Y.-Q., Wu G.-Q., Li Y.-B., Dai Z., and Chen B.H. Synth. Commun. 36 (2006) 3353
48. Han W., Liu C., and Jin Z.-L. Org. Lett. 9 (2007) 4005
49. Winter A., Van den Berg A.M.J., Hoogenboom R., Kickelbick G., and Schubert U.S. Synthesis (2006) 2873
50. Kouznetsov V.V., Romero Bohórquez A.R., and Stashenko E.E. Tetrahedron Lett. 48 (2007) 8855
51. Kouznetsov V.V., Romero Bohórquez A.R., Astudillo L., and Fierro R. Mol. Divers. 10 (2006) 29
52. Kouznetsov V.V., Zubkov F.I., Mora U., Voskressensky L.G., Vargas L.Y., Astudillo L., and Stashenko E.E. Lett. Org. Chem. 1 (2004) 37
53. Kouznetsov V.V., and Mora U. Lett. Org. Chem. 3 (2006) 699
54. Kouznetsov V.V., Zubkov F.I., Mora U., and Nikitina E.V. Synthesis (2007) 375
55. 4: C, 70.75; H, 5.68; N, 7.17. Found: C, 70.59; H, 5.84; N, 7.02. All the products 9d-f were characterized by comparing their physical and spectral data with those of reported compounds (see, Ref. 15).
56. 4, see:. Fadel F., Titouni S.L., Soufioui M., Ajamay H., and Mazzah A. Tetrahedron Lett. 45 (2004) 5905
57. Zhang W., Guo Y., Liu Z., Jin X., Yang L., and Liu Z.-L. Tetrahedron 61 (2005) 1325
58. 2 was added into the mixture. Finally, trans-isoeugenol (or trans-anethole) was added dropwise to the reaction mixture. The temperature was kept to 70 °C under inert atmosphere (nitrogen) for 10 h. After complete conversion, as indicated by TLC, the crude product was purified by column chromatography without previous extraction to obtain tetrahydroquinolines 9a-f.
59. 2 was employed, the same procedure was used as described above.