One-pot synthesis of N-substituted 2-methyl-4,5,6,7-tetrahydroindole derivatives

Tetrahedron Letters

Volumn 45, Issue 52, 2004, Pages 9627-9629

  Tanyeli, Cihangir ^a   Akhmedov, Idris M ^a   Yazicioǧlu, Emre Y ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

4,5,6,7 Tetrahydroindoles; Enamines

Indexed keywords

2 (2 BROMOALLYL)CYCLOHEXANONE; ALIPHATIC AMINE; AROMATIC AMINE; CYCLOHEXANONE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; POLYMERIZATION; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS; TRANSAMINATION;

EID: 9644291758     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.145     Document Type: Article

References (29)

1. H. Stetter, and E. Siehnhold Chem. Ber. 88 1955 271
2. J.M. Patterson, and S. Soedigdo J. Org. Chem. 32 1967 2969
3. F.M. Hershenson J. Org. Chem. 40 1975 1260
4. D. Dhanak, C.B. Reese, S. Romana, and G. Zappia J. Chem. Soc., Chem. Commun. 12 1986 903
5. G. Chelucci, S. Gladiali, and M. Marchetti J. Heterocycl. Chem. 25 1988 1761
6. D. Enders, S.H. Han, and R. Maaßen Tetrahedron Lett. 36 1995 8007
7. S. Lim, I. Jabin, and G. Revial Tetrahedron Lett. 40 1999 4177
8. H.M.C. Ferraz, F.L.C. Pereira, F.M. Leita, M.R.S. Nunes, and M.E. Payret-Arrua Tetrahedron 55 1999 10915
9. H.M.C. Ferraz, E.O. Oliviera, M.E. Payret-Arrua, and C.A. Brandt J. Org. Chem. 60 1995 7357
10. M. Mori, M. Akashi, and M. Nishida Chem. Lett. 1999 465
11. S. Fukumoto, E. Imamiya, K. Kusumoto, T. Watanabe, and M. Shiraishi J. Med. Chem. 45 2002 3009
12. A.S. Demir, İ.M. Akhmedov, and O. Sesenoglu Tetrahedron 58 2002 9793
13. M. Mori, Y. Uozumi, and M. Shibasaki Heterocycles 33 1992 819
14. W.A. Remers, and M.J. Weiss J. Org. Chem. 30 1965 5232
15. C.F. Masaguer, and E. Ravina Tetrahedron Lett. 37 1996 5171
16. L. Sun, N. Tran, C. Liang, S. Hubbard, F. Tang, K. Lipson, R. Schreck, Y. Zhou, G. McMahon, and C. Tang J. Med. Chem. 43 2000 2655
17. Oba, T.; Tanaka, T.; Okamura, N.; Watanabe, K.; Bannai, K.; Ohtsu, A.; Naruchi, T.; Kurozumi, S.; Toru, T. Eur. Pat. Appl., 1981, 145 pp; Chem. Abstr. 1981, 95:24812
18. C.C. McComas, and D.L. Van Vranken Tetrahedron Lett. 40 1999 8039
19. S. O'Brien, and D.C.C. Smith J. Chem. Soc. 1960 4609
20. D.V. Young, and H.R. Snyder J. Am. Chem. Soc. 83 1961 3160
21. R. Greenhouse, C. Ramirez, and J.M. Muchowski J. Org. Chem. 50 1985 2962
22. N. De Kimpe, and M. Keppens Tetrahedron 52 1996 3705
23. M. Mori, Y. Washioka, T. Urayama, K. Yoshiura, K. Chiba, and Y. Bon J. Org. Chem. 48 1983 4058
24. A. Arcadi, and E. Rossi Tetrahedron 54 1998 15253
25. H. Nagano, Y. Ohtani, E. Odake, J. Nakagawa, Y. Mori, and T. Yajima J. Chem. Res. (S) 5 1999 338
26. +, 240.1752. Found 240.1746
27. General procedure for 'Method B: Starting compound 1 (0.31 g, 1.43 mmol) was mixed with 1.1 equiv of aniline (0.15 g, 1.57 mmol) in dry toluene (30 mL), with p-toluenesulfonic acid (10 mg, 0.06 mmol) under argon and the mixture was refluxed for 3 h using a Dean-Stark trap. After evaporation of the solvent in vacuo, dry dimethyl sulfoxide (3 mL) was added together with 1.1 equiv of potassium tert-butoxide (0.28 g, 2.46 mmol) and the reaction mixture was kept at 80°C for 4 h. The reaction mixture was allowed to reach room temperature and purification by flash column chromatography afforded compound 3a as a yellow oil (0.27 g, 98%)
28. 3) δ (ppm): 139.3, 129.4, 128.5, 128.3, 127.7, 117.3, 106.3, 24.4, 24.1, 23.6, 23.5, 13.2
29. For spectroscopic data of 2d see: H. Ahlbrecht, and A. Von Daacke Synthesis 7 1984 610