New syntheses of pyrrolo[3,4-b]indoles, benzo[b]furo[2,3-c]pyrroles, and benzo[b]thieno [2,3-c]pyrroles utilizing the reaction of münchnones (1,3-oxazolium-5-olates) with nitroheterocycles

Synlett

Volumn , Issue 10, 1998, Pages 1061-1062

  Gribble, Gordon W ^a   Pelkey, Erin T ^a   Switzer, Frank L ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002513978     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1887     Document Type: Article

References (20)

1. Pelkey, E.T.; Gribble, G.W. Chem. Commun. 1997, 1873, and references cited therein.
2. For other syntheses of pyrrolo[3,4-b]indoles, see a) Welch, W.M. J. Org. Chem. 1976, 41, 2031.
3. b) Sha, C.-K.; Chuang, K.-S.; Young, J.-J. J. Chem. Soc., Chem. Commun. 1984, 1552.
4. c) Sha, C.-K.; Chuang, K.-S.; Wey, S.-J. J. Chem. Soc., Perkin Trans. 1 1987, 977.
5. d) Sha, C.-K.; Yang, J.-F. Tetrahedron 1992, 48, 10645.
6. e) Kreher, R.P.; Dyker, G. Z Naturforsch, Teil B: Chem. Sci. 1987, 42, 473.
7. f) Dyker, G.; Kreher, R.P. Chem.-Ztg. 1988, 112, 235.
8. g) Jeevenandam, A.; Srinivasan, P.C. J. Chem. Soc., Perkin Trans. 1 1995, 2663.
9. h) Daly, K.; Nomak, R.; Snyder, J.K. Tetrahedron Lett. 1997, 38, 8611.
10. i) Pelkey, E.T.; Chang, L.; Gribble, G.W. J. Chem. Soc, Chem. Commun. 1996, 1909.
11. j) Ref. 1.
12. This was prepared from 2-nitroindole (Pelkey, E.T.; Gribble, G.W. Tetrahedron Lett. 1997, 38, 5603) and sodium hydride and ethyl chloroformate in DMF (74% yield).
13. a) Gribble, G.W.; Switzer, F.L.; Bushweller, J.H.; Jewett, J.G.; Brown, J.H.; Dion, J.L.; Bushweller, C.H.; Byrn, M.P.; Strouse, C.E. J. Org. Chem. 1996, 61, 4319.
14. b) Gribble, G.W; Sponholtz III, W.R.; Switzer, F.L.; D'Amato, F.J.; Byrn, M.P. Chem. Commun. 1997, 993.
15. 4
16. 17NS: 291.1082. Found: 291.1084.
17. 3): 5: δ 8.33-.8.35 (m, 1 H), 7.10-7.59 (m, 16 H), 6.58-6.64 (m, 2 H), 5.10 (s, 2 H), 3.74 (q, 2 H, J = 7.2 Hz), 0.80 (t, 3 H, J = 7.2 Hz); 6: δ 8.19-8.20 (m, 1 H), 7.61-7.64 (m, 1 H), 7.19-7.34 (m, 5 H), 6.91-6.93 (m, 2 H), 5.19 (s, 2 H), 4.50 (q, 2 H, J= 7.2 Hz), 2.56 (s, 3 H), 2.49 (s, 3 H), 1.49 (t, 3 H, J = 7.2 Hz); 11: δ 8.20-8.23 (m, 1 H), 7.11-7.47 (m, 21 H), 6.58-6.60 (m, 2 H), 5.11 (s, 2 H); 15: δ 7.67-7.70 (m, 1 H), 7.58-7.64 (m, 4 H), 7.27-7.50 (m, 8 H), 7.14-7.20 (m, 4 H), 6.74-6.77 (m, 2 H), 5.46 (s, 2 H); 16: δ 7.61-7.64 (m, 1 H), 7.17-7.38 (m, 6 H), 6.89-6.92 (m, 2 H), 5.16 (s, 2 H), 2.46 (s, 3 H), 2.31 (s, 3 H); 17: δ 7.66-7.69 (m, 1 H), 7.39-7.54 (m, 10 H), 7.11-7.31 (m, 6 H), 6.68-6.71(m, 2 H), 5.37 (s, 2 H); 18: δ 7.77-7.80 (m, 1 H), 7.64-7.67 (m, 1 H), 7.17-7.34 (m, 5 H), 6.90-6.93 (m, 2 H), 5.20 (s, 2 H), 2.55 (s, 3 H), 2.31 (s, 3 H).
18. Tromelin, A.; Demerseman, P.; Royer, R. Synthesis 1985, 1074.
19. Ono, N.; Hironaga, H.; Ono, K.; Kaneko, S.; Murashima, T.; Ueda, T.; Tsukamura, C.; Ogawa, T. J. Chem. Soc., Perkin Trans. 1 1996, 417.
20. Nesi, R.; Giomi, D.; Turchi, S.; Tedeschi, P.; Ponticelli, F. Gazz. Chim. Ital. 1993, 123, 633.