200
N. V. Moskale6, G. W. Gribble / Tetrahedron Letters 43 (2002) 197–201
8. For a review of heterocyclic o-quinodimethanes, see:
3.6), 6.30 (d, 1H, 3.6), 5.40 (q, 1H), 4.81 (t, 1H), 3.39 (br
s, 1H), 2.95 (br s, 1H), 1.79 (m, 2H), 1.42 (d, 3H), 0.96 (t,
3H); MS m/z 332 (MNa+). Anal. calcd for C15H19NO4S:
C, 58.25; H, 6.15; N, 4.53; S, 10.36. Found: C, 58.46; H,
6.14; N, 4.62; S, 10.43.
Collier, S. J.; Storr, R. C. Prog. Heterocyclic Chem. 1998,
10, 25–48.
9. (a) Clark, D. T. J. Mol. Spectrosc. 1968, 26, 181–188; (b)
Klasinc, L.; Trinajstic, N. Tetrahedron 1971, 27, 4045–
4052; (c) Milun, M.; Trinajstic, N. Croat. Chem. Acta
1977, 49, 107–113; (d) Buemi, G. J. Chim. Phys. Phys.
Chim. Biol. 1987, 84, 1147–1160; (e) Friedl, Z.; Balkova,
A.; Krutosikova, A. Stud. Org. Chem. 1988, 35, 276–278;
(f) Subramanian, G.; Schleyer, P.v. R.; Jiao, H. Angew.
Chem., Int. Ed. Engl. 1996, 35, 2638–2640; (g) Novak, I.
THEOCHEM 1997, 398–399, 315–323.
10. (a) Saulnier, M. G.; Gribble, G. W. Tetrahedron Lett.
1983, 24, 5435–5438; (b) Gribble, G. W.; Saulnier, M. G.;
Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49,
4518–4523; (c) Gribble, G. W.; Saulnier, M. G. J. Chem.
Soc., Chem. Commun. 1984, 168–169; (d) Davis, D. A.;
Gribble, G. W. Tetrahedron Lett. 1990, 31, 1081–1084; (e)
Gribble, G. W.; Keavy, D. J.; Davis, D. A.; Saulnier, M.
G.; Pelcman, B.; Barden, T. C.; Sibi, M. P.; Olson, E. R.;
BelBruno, J. J. J. Org. Chem. 1992, 57, 5878–5891; (f)
Gribble, G. W.; Silva, R. A.; Saulnier, M. G. Synth.
Commun. 1999, 29, 729–747.
21. Compound 8 (1-[3-(1-hydroxypropyl)-1-(phenylsulfonyl)-
1H-pyrrol-2-yl]-1-ethanone): mp 60°C (dec.); 1H NMR
(CDCl3) l 7.80 (m, 2H), 7.67–7.48 (m, 3H), 7.31 (d, 1H,
3.3), 6.36 (d, 1H, 3.3), 4.57 (m, 1H), 2.64 (s, 3H), 2.40 (d,
1H), 1.74 (m, 2H), 0.90 (t, 3H).
Compound 9 (1-12-(1-hydroxyethyl)-1-(phenylsulfonyl)-
1H-pyrrol-3-yl]-1-propanone): mp 86° (dec.); IR (film)
wmax 3300, 1723, 1656, 1542, 1404, 1170, 1138, 1090 cm−1
;
1H NMR (CDCl3) l 7.90 (m, 2H), 7.75–7.57 (m, 3H),
7.38 (d, 1H, 3.6), 6.71 (d, 1H, 3.6), 6.06 (d, 1H), 5.39 (m,
1H), 2.90 (q, 2H), 2.70 (s, 3H), 1.16 (t, 3H); MS m/z 330
(MNa+).
22. Compound 10 (1-[2-acetyl-1-(phenylsulfonyl)-1H-pyrrol-
3-yl]-1-propanone): mp 80–81°C; IR (film) wmax 3054,
2985, 1709, 1678, 1264 cm−1 1H NMR (CDCl3) l 7.80
;
(m, 2H), 7.74–7.56 (m, 3H), 7.20 (d, 1H, 3.3), 6.57 (d, 1H,
3.3), 2.78 (q, 2H), 2.70 (s, 3H), 1.16 (t, 3H); MS m/z 306
(MH+).
11. (a) Pelkey, E. T.; Gribble, G. W. Chem. Commun. 1997,
1873–1874; (b) Gribble, G. W.; Pelkey, E. T.; Switzer, F.
L. Synlett 1998, 1061–1062; (c) Pelkey, E. T.; Gribble, G.
W. Synthesis 1999, 1117–1122; (d) Gribble, G. W.;
Pelkey, E. T.; Simon, W. M.; Trujillo, H. A. Tetrahedron
2000, 56, 10133–10140; (e) For a review, see: Sha, C.-K.
Adv. Nitrogen Heterocycles 1996, 2, 147–178.
12. Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89,
1681–1689.
13. For a recent review, see: Gribble, G. W. J. Chem. Soc.,
Perkin Trans. 1 2000, 1045–1075.
23. Compound 12 (4-ethyl-6,8-dimethyl-1-(phenylsulfonyl)-
pyrrolo[3,4-f ]indole-5,7-(1H,6H)-dione): mp 166–167°C;
IR (Nujol) wmax 1752, 1693, 1457, 1377, 1269 cm−1; umax
1
(CHCl3) 254, 344 nm; H NMR (CDCl3) l 8.07 (d, 1H,
3.6), 7.76–7.54 (m, 5H), 6.96 (d, 1H, 3.6), 3.34 (q, 2H),
3.14 (s, 3H), 2.90 (s, 3H), 1.31 (t, 3H); 13C NMR (CDCl3)
l 169.6, 168.5, 139.6, 137.9, 136.6, 136.2, 134.4, 133.1,
129.8, 126.7, 126.1, 125.0, 123.6, 107.1, 23.9, 21.5, 15.3,
14.9; MS m/z 382 (M+, 96%), 241 (100%), 234, 141, 85,
77. Anal. calcd for C20H18N2O4S: C, 62.81; H, 4.74; N,
7.33; S, 8.38. Found: C, 62.88; H, 4.82; N, 7.26; S, 8.37.
24. Compound 13 (4-ethyl-8-methyl-6-phenyl-1-(phenylsul-
fonyl)pyrrolo[3,4-f ]indole-5,7-(1H,6H)-dione): mp 158–
160°C; IR (Nujol) wmax 1757, 1713, 1597, 1502, 1451,
14. (a) Jackson, P. M.; Moody, C. J. J. Chem. Soc., Perkin
Trans. 1 1990, 2156–2158; (b) Jackson, P. M.; Moody, C.
J. Tetrahedron 1992, 48, 7447–7466.
15. Zelikin, A.; Shastri, V. R.; Langer, R. J. Org. Chem.
1
1377 cm−1; umax (CHCl3) 256, 346 nm; H NMR (CDCl3)
1999, 64, 3379–3380.
l 8.12 (d, 1H, 3.9), 7.77–7.44 (m, 10H), 7.02 (d, 1H, 3.9),
3.40 (q, 2H), 2.96 (s, 3H), 1.35 (t, 3H); 13C NMR
(CDCl3) l 168.4, 167.3, 139.6, 138.2, 137.1, 136.8, 134.4,
132.1, 129.9, 129.1, 128.1, 127.0, 126.7, 125.6, 125.5,
123.2, 107.1, 21.7, 15.2, 15.0; MS m/z 444 (M+, 70%), 303
(100%), 259, 141, 83, 77. Anal. calcd for C25H20N2O4S:
C, 67.55; H, 4.54; N, 6.30; S, 7.21. Found: C, 67.33; H,
4.66; N, 6.28; S, 7.13.
16. Ketcha, D. M.; Carpenter, K. P.; Atkinson, S. T.;
Rajagopalan, H. R. Synth. Commun. 1990, 20, 1647–1655
and references cited therein.
17. Compound 6: oil; IR (film) wmax 3553, 3384, 1583, 1476,
1
1369, 1174, 1061 cm−1; umax (CHCl3) 256 nm; H NMR
(CDCl3) l 7.90 (m, 2H), 7.65–7.50 (m, 3H), 7.16 (m, 1H),
7.13 (m, 1H), 6.32 (m, 1H), 4.04 (t, 1H), 1.74 (q, 3H),
0.91 (t, 3H); MS m/z 265 (M+, 5%), 247, 236, 141, 77, 58
(100%): HRMS m/z calcd for C13H15NO3S (M+):
265.0773; found: 265.0776.
25. Compound 14 (4-ethyl-8-methyl-1-(phenylsulfonyl)-1H-
furo[3,4-f ]indole-5,7-dione): mp 195–196°C; IR (Nujol)
wmax 1823, 1762, 1460, 1377, 1286 cm−1; umax (CHCl3)
256, 340 nm; 1H NMR (CDCl3) l 8.20 (d, 1H, 3.9),
7.79–7.58 (m, 5H), 7.04 (d, 1H, 3.9), 3.34 (q, 2H), 2.90 (s,
3H), 1.34 (t, 3H); 13C NMR (CDCl3) l 163.9, 162.9,
139.3, 138.7, 138.6, 138.4, 134.8, 134.7, 130.0, 127.0,
126.8, 124.9, 122.4, 106.9, 21.9, 15.2, 15.1; MS m/z 369
(M+, 37%), 141 (100%), 77. Anal. calcd for C19H15NO5S:
C, 61.78; H, 4.09; N, 3.79; S, 8.68. Found: C, 61.48; H,
4.08; N, 3.76; S, 8.54.
18. This diol (1-[5-(1-hydroxyethyl)-1-(phenylsulfonyl)-1H-
pyrrol-3-yl]-1-propanol) is an oil; 1H NMR (CDCl3) l
7.84 (m, 2H), 7.70–7.40 (m, 3H), 7.25 (m, 1H), 6.35 (m,
1H), 5.02 (q, 1H), 4.54 (t, 1H), 1.74 (q, 3H) (overlapping
with OH), 1.50 (d, 3H), 0.94 (t, 3H).
19. This sultone (3-methyl-2,1-l6-benzoxathiole-1,1-(3H)-
1
dione) has mp 85–87°C; H NMR (CDCl3) l 7.83 (d, 1H,
7.8), 7.73 (m, 1H), 7.60 (m, 1H), 7.42 (d, 1H, 7.8), 5.84
(q, 1H, 6.6), 1.81 (d, 3H, 6.6). Anal. calcd for C8H8O3S:
C, 52.16; H, 4.38; S, 17.40. Found: C, 52.47; H, 4.33; S,
17.46.
26. Moskalev, N. V.; Jasinski, J. P.; Gribble, G. W., unpub-
lished results.
27. Compound
18
(4,8-dimethyl-1-(phenylsulfonyl)-1H-
20. Compound
7 (1-[2-(1-hydroxyethyl)-1-(phenylsulfonyl)-
1H-pyrrol-3-yl]-1-propanol): mp 106–108°C; 1H NMR
(CDCl3) l 7.78 (m, 2H), 7.68–7.50 (m, 3H), 7.28 (d, 1H,
furo[3,4-f ]indole-5,7-dione): mp 209–211°C; IR (Nujol)
wmax 1827, 1761, 1371, 1290 cm−1; umax (CHCl3) 258, 340