Regioselective synthesis of functionalized 4-nitro- and 4-amino-phenols based on formal [3+3] cyclocondensations of 3-ethoxy-2-nitro-2-en-1-ones with 1,3-bis(silyloxy)-1,3-butadienes

Tetrahedron Letters

Volumn 50, Issue 25, 2009, Pages 3017-3019

  Riahi, Abdolmajid ^a,b   Shkoor, Mohanad ^a   Khera, Rasheed Ahmad ^a   Reinke, Helmut ^a   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Aminophenols; arenes; Cyclizations; Regioselectivity; Silyl enol ethers

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 4 AMINOPHENOL; 4 NITROPHENOL;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; ELIMINATION REACTION; HYDROGENATION; POLYMERIZATION; REACTION ANALYSIS; SILYLATION; SYNTHESIS;

EID: 65449164906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.190     Document Type: Article

References (46)

1. In: Steglich W., Fugmann B., and Lang-Fugmann S. (Eds). Römpp Lexikon Naturstoffe (1997), Thieme, Stuttgart
2. Li C., Taneda S., Suzuki A.K., Furuta C., Watanabe G., and Taya K. Eur. J. Pharmacol. 543 (2006) 194
3. Yoki K., Kamata K., Toda N., Hayashi H., Seki K.-i., Taneda S., Yoshino S., Sakushima A., Sakata M., and Suzuki A.K. Biol. Pharm. Bull. 26 (2003) 394
4. Bitsch N., Dudas C., Koerner W., Failing K., Biselli S., Rimkus G., and Brunn H. Arch. Environ. Contam. Toxicol. 43 (2002) 257
5. Api A.M., and Gudi R. Mutat. Res. 464 (2000) 263
6. Lehman-McKeeman L.D., Caudill D., Vassallo J.D., Pearce R.E., Madan A., and Parkinson A. Toxicol. Lett. 111 (1999) 105
7. Nadin L., and Murray M. Biochem. Pharmacol. 58 (1999) 1201
8. Fent K., Escher C., and Caminada D. Reprod. Toxicol. 22 (2006) 175
9. Khamdang S., Takeda M., Noshiro R., Narikawa S., Enomoto A., Anzai N., Piyachaturawat P., and Endou H. J. Pharmacol. Exp. Ther. 303 (2002) 534
10. Gobec S., Brozic P., and Rizner T.L. Bioorg. Med. Chem. Lett. 15 (2005) 5170
11. Tran T., Saheba E., Arcerio A.V., Chavez V., Li Q.-y., Martinez L.E., and Primm T.P. Bioorg. Med. Chem. 12 (2004) 4809
12. Alvi K.A., Nair B., Gallo C., and Baker D. J. Antibiot. 50 (1997) 264
13. de Oliveira M.F., Oliveira J.H.H.L., Galetti F.C.S., de Souza A.O., Silva C.L., Hajdu E., Peixinho S., and Berlinck R.G.S. Planta Med. 72 (2006) 437
14. Lee J., Chubb A.J., Moman E., McLoughlin B.M., Sharkey C.T., Kelly J.G., Nolan K.B., Devocelle M., and Fitzgerald D.J. Org. Biomol. Chem. 3 (2005) 3678
15. Alvi K.A., Diaz M.C., Crews P., Slate D.L., Lee R.H., and Moretti R. J. Org. Chem. 57 (1992) 6604
16. Ismail L.D., Lorenz P., and Stermitz F. J. Nat. Prod. 61 (1998) 1174
17. Davies J., Wang H., Taylor T., Warabi K., Huang X.-H., and Andersen R.J. Org. Lett. 7 (2005) 5233
18. Thale Z., Johnson T., Tenney K., Wenzel P.J., Lobkovsky E., Clardy J., Media J., Pietraszkiewicz H., Valeriote F.A., and Crews P. J. Org. Chem. 67 (2002) 9384
19. Werbel L.M., Cook P.D., Elslager E.F., Hung J.H., and Johnson J.L. J. Med. Chem. 29 (1986) 924
20. Take K., Okumura K., Takimoto K., Kato M., Ohtsuka M., and Shiokawa Y. Chem. Pharm. Bull. 39 (1991) 2915
21. Astles P.C., Brown T.J., Cox P., Halley F., and Lockey P.M. Bioorg. Med. Chem. Lett. 7 (1997) 907
22. Ukita T., Nakamura Y., Kubo A., Yamamoto Y., and Takahashi M. J. Med. Chem. 42 (1999) 1293
23. Sun L., Tran N., Liang C., Tang F., Rice A., Schreck R., Waltz K., Shawver L.K., McMahon G., and Tang C. J. Med. Chem. 42 (1999) 5120
24. Poupart M.-A., Cameron D.R., Chabot C., Ghiro E., Goudreau N., Goulet S., Poirier M., and Tsantrizos Y.S. J. Org. Chem. 66 (2001) 4743
25. Parikh V., Welch W.M., and Schmidt A.W. Bioorg. Med. Chem. Lett. 13 (2003) 269
26. Wang L., Wang G.T., Wang X., Tong Y., Sullivan G., Park D., Leonard N.M., Li Q., Cohen J., Gu W.-Z., and Zhang H. J. Med. Chem. 47 (2004) 612
27. Sheppard G.S., Kawai M., Craig R.A., Davidson D.J., Majest S.M., Bell R.L., and Henkin J. Bioorg. Med. Chem. Lett. 14 (2004) 965
28. Mor M., Rivara S., Lodola A., Plazzi P.V., Tarzia G., Duranti A., Tontini A., Piersanti G., Kathuria S., and Piomelli D. J. Med. Chem. 47 (2004) 4998
29. Hayakawa I., Shioya R., Agatsuma T., Furukawa H., Naruto S., and Sugano Y. Bioorg. Med. Chem. Lett. 14 (2004) 4383
30. Poesche W.H. J. Chem. Soc. C (1966) 890
31. Forrest J. J. Chem. Soc. (1960) 589
32. Helmchen G., and Prelog V. Helv. Chim. Acta 55 (1972) 2599
33. Suzuki H., Enya T., and Hisamatsu Y. Synthesis (1997) 1273
34. Bell A.J., and Read R.W. Aust. J. Chem. 40 (1987) 1813
35. Kleppinger R., Lillya C.P., and Yang C. J. Am. Chem. Soc. 119 (1997) 4097
36. Mohanakrishnan A.K., and Srinivasan P.C. J. Org. Chem. 60 (1995) 1939
37. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions (2004), Wiley-VCH, Weinheim
38. Ashburn B.O., Carter R.G., and Zakharov L.N. J. Am. Chem. Soc. 129 (2007) 9109
39. Chan T.-H., and Brownbridge P. J. Am. Chem. Soc. 102 (1980) 3534
40. For a review of 1,3-bis(silyloxy)-1,3-butadienes, see:. Langer P. Synthesis (2002) 441
41. Review:. Feist H., and Langer P. Synthesis (2007) 327
42. Nakamatsu S., Yoshizawa K., Toyota S., Toda F., and Matijasic I. Org. Biomol. Chem. 1 (2003) 13
43. Field G.F., and Zally S. Synthesis (1979) 295
44. +): 273.06317; found: 273.063020.
45. +): 243.08899; found: 243.089209.
46. CCDC-720054 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.