7-(tr a n s-2-Cin n a m yl)-2-m eth ylin d olin e (1c): FTIR 3382,
1602, 1477, 1458; 1H NMR 1.26 (d, J ) 6.2 Hz, 3H), 2.64 (dd, J 1
) 15.5 Hz, J 2 ) 7.7 Hz, 1H), 3.16 (dd, J 1 ) 15.5 Hz, J 2 ) 8.5 Hz,
1H), 3.40 (d, J ) 6.0 Hz, 2H), 3.78 (br s, 1H), 3.96 (m, 1H), 6.27-
6.36 (dt, J 1 ) 15.8 Hz, J 2 ) 6.0 Hz, 1H), 6.45 (d, J ) 15.8 Hz,
1H), 6.69 (t, J ) 7.4 Hz, 1H), 6.91 and 7.00 (d + d, J ) 7.4 Hz,
1H + 1H), 7.20-7.39 (m, 5H); 13C NMR 22.4 (CH3), 35.3 (CH2),
37.8 (CH2), 55.1 (CH), 118.8 (CH), 120.4 (CH), 122.9-130.9 (CH
and C), 137.3 (C), 149.6 (C); MS 249 (M+, 100), 234 (61), 130
(38), 117 (97), 91 (19). Exact mass calcd for C18H19N 249.1517,
found 249.1512.
1.00 (d, J ) 6.3 Hz, 3H), 1.99-2.24 (m, 2H), 2.49-2.83 (m, 3H),
3.14 (dd, J 1 ) 15.3 Hz, J 2 ) 8.5 Hz, 1H), 3.68-3.80 (m, 1H),
4.31 (dd, J 1 ) 7.8 Hz, J 2 ) 3.5 Hz, 1H), 6.57 (t, J ) 7.3 Hz, 1H),
6.83 and 6.93 (d + d, J ) 7.3 Hz, 1H + 1H), 7.23-7.37 (m, 5H);
13C NMR 16.9 (CH3), 23.4 (CH2), 32.6 (CH2), 36.7 (CH2), 56.1
(CH), 56.7 (CH), 116.9 (CH), 117.9 (CH), 122.4-128.4 (CH and
C), 142.6 (C), 148.2 (C); MS 249 (M+, 77), 248 (4), 234 (100), 172
(31), 130 (30), 117 (52), 77 (6). Exact mass calcd for C18H19
249.1517, found 249.1509.
N
cis-2-Meth yl-4-ph en yl-1,2,5,6-tetr ah ydr o-4H-pyr r olo[3,2,1-
1
ij]qu in olin e (cis-4): FTIR 1601, 1479, 1346; H NMR 0.86 (d,
2-Meth yl-7-(3-p h en ylp r op yl)in d olin e (1c-H): FTIR 3377,
J ) 6.1 Hz, 3H), 1.89-2.20 (m, 2H), 2.49-2.70 (m, 3H), 3.04
1
1601, 1456, 746, 700; H NMR 1.22 (d, J ) 6.2 Hz, 3H), 1.83-
(dd, J 1 ) 15.7 Hz, J 2 ) 8.0 Hz, 1H), 3.60 (m, 1H), 3.99 (dd, J 1
)
2.78 (m, 7H), 3.07 (dd, J 1 ) 15.5 Hz, J 2 ) 8.6 Hz, 1H), 3.90 (m,
1H), 6.60 (t, J ) 7.4 Hz, 1H), 6.80 and 6.88 (d + d, J ) 7.4 Hz,
1H + 1H), 7.09-7.29 (m, 5H); 13C NMR 22.2 (CH3), 29.7 (CH2),
30.5 (CH2), 35.5 (CH2), 37.9 (CH), 55.1 (CH), 117.5-142.0 (CH
and C); MS 251 (M+, 100), 236 (76), 207 (12), 147 (71), 130 (36),
118 (22), 91 (65). Exact mass calcd for C18H21N 251.1674, found
251.1670.
5.8 Hz, J 2 ) 4.6 Hz, 1H), 6.61 (t, J ) 7.3 Hz, 1H), 6.85 and 6.94
(d + d, J ) 7.3 Hz, 1H + 1H), 7.23-7.37 (m, 5H); 13C NMR 15.3
(CH3), 22.8 (CH2), 31.6 (CH2), 38.2 (CH2), 64.1 (CH), 65.8 (CH),
117.5 (CH), 119.0 (CH), 121.6 (CH), 125.8-128.1 (CH and C),
145.5 (C), 149.9 (C); MS 249 (M+, 79), 248 (6), 247, (3), 234 (100),
172 (32), 130 (31), 117 (54), 77 (6). Exact mass calcd for C18H19
249.1517, found 249.1512.
N
1-Allyl-2-p h en yl-1,2,3,4-tetr a h yd r oqu in olin e (2b): FTIR
1602, 1498, 744; 1H NMR 2.00-2.22 (m, 2H), 2.53-2.60 (dd, J 1
) 7.5 Hz, J 2 ) 4.4 Hz, 2H), 3.58 and 4.06 (m + m, 2H), 4.59 (t,
J ) 7.4 Hz, 1H), 5.08-5.20 (m, 2H), 5.75-5.84 (m, 1H), 6.60 (t,
J ) 7.3 Hz, 1H), 6.66 (d, J ) 8.2 Hz, 1H), 6.97 (d, J ) 7.3 Hz,
1H), 7.09 (m, 1H), 7.16-7.32 (m, 5H); 13C NMR 23.8 (CH2), 29.6
(CH2), 51.7 (CH2), 60.7 (CH), 110.3 (CH), 115.4-133.4 (CH2, CH
and C), 144.3 (C), 144.9 (C); MS 249 (M+, 96), 222 (16), 208 (32),
172 (100), 144 (14), 130 (41), 91 (29), 77 (12). Exact mass calcd
for C18H19N 249.1517, found 249.1519.
tr a n s-2-Ben zyl-4-m eth yl-1,2,4,5-tetr a h yd r op yr r olo[3,2,1-
h i]in d ole (tr a n s-5): FTIR 1591, 1475, 1454, 750, 700; 1H NMR
0.84 (d, J ) 6.5 Hz, 3H), 2.73 (dd, J 1 ) 15.1 Hz, J 2 ) 3.5 Hz,
1H), 2.85 (dd, J 1 ) 13.5 Hz, J 2 ) 7.3 Hz, 1H), 2.98-3.28 (m,
3H), 3.43 (dd, J 1 ) 15.1 Hz, J 2 ) 7.7 Hz, 1H), 3.78 (m, 1H), 4.01
(m, 1H), 6.55 (t, J ) 7.2 Hz, 1H), 6.84 (m, 2H), 7.16-7.33 (m,
5H); 13C NMR 16.3 (CH3), 40.5 (CH2), 40.7 (CH2), 42.2 (CH2),
60.2 (CH), 65.7 (CH), 119.4-129.6 (CH and C), 139.7 (C); MS
249 (M+, 8), 158 (100), 130 (19), 117 (21), 91 (8). Exact mass
calcd for C18H19N 249.1517, found 249.1518.
1-(tr a n s-2-Cin n a m yl)-2-m eth ylin d olin e (2c): FTIR 1604,
1483, 746; 1H NMR 1.32 (d, J ) 6.1 Hz, 3H), 2.63 (dd, J 1 ) 15.4
Hz, J 2 ) 9.8 Hz, 1H), 3.12 (dd, J 1 ) 15.4 Hz, J 2 ) 8.5 Hz, 1H),
3.66-4.04 (m, 3H), 6.20-6.31 (ddd, J 1 ) 15.8 Hz, J 2 ) 7.0 Hz,
J 3 ) 4.8 Hz, 1H), 6.50 (d, J ) 8.0 Hz, 1H), 6.62 (d, J ) 15.8 Hz,
1H), 6.65 (t, J ) 7.3 Hz, 1H), 7.04 (m, 2H), 7.16-7.39 (m, 5H);
13C NMR 19.4 (CH3), 37.3 (CH2), 48.7 (CH2), 59.9 (CH), 107.1
(CH), 117.5 (CH), 124.1-131.7 (CH and C), 136.9 (C), 152.2 (C);
MS 249 (M+, 48), 234 (10), 130 (5), 117 (100), 91 (15). Exact mass
calcd for C18H19N 249.1517, found 249.1507.
cis-2-Ben zyl-4-m eth yl-1,2,4,5-tetr a h yd r op yr r olo[3,2,1-h i]-
in d ole (cis-5): FTIR 1591, 1471, 1340, 1279, 750, 700; 1H NMR
1.42 (d, J ) 6.2 Hz, 3H), 2.90-3.28 (m, 6H), 3.40-3.61 (m + m,
1H + 1H), 6.57 (t, J ) 7.2 Hz, 1H), 6.78 and 6.84 (d + d, J ) 7.2
Hz, 1H + 1H), 7.17-7.33 (m, 5H); 13C NMR 21.1 (CH3), 41.2
(CH2), 42.2 (CH2), 43.6 (CH2), 69.1 (CH), 74.4 (CH) 120.3-129.4
(CH and C), 139.2 (C); MS 249 (M+, 9), 158 (100), 130 (18), 117
(21), 91 (8). Exact mass calcd for C18H19N 249.1517, found
249.1512.
5-(-tr a n s-2-Cin n a m yl)-2-m eth ylin d olin e (3c): FTIR 3371,
1616, 1491, 1450, 1250; H NMR 1.25 (d, J ) 6.2 Hz, 3H), 2.57
Ackn owledgm en t. Financial support from the Span-
ish MCYT (Grant No. BQU 2001-2725) and the Gener-
alitat Valenciana (Grant GV01-272) is gratefully ac-
knowledged.
1
(dd, J 1 ) 15.5 Hz, J 2 ) 7.9 Hz, 1H), 3.08 (dd, J 1 ) 15.5 Hz, J 2
) 8.4 Hz, 1H), 3.41 (d, J ) 6.1 Hz, 2H), 3.52 (br s, 1H), 3.93 (m,
1H), 6.26-6.38 (dt, J 1 ) 15.7 Hz, J 2 ) 6.1 Hz, 1H), 6.41 (d, J )
15.7 Hz, 1H), 6.52 (d, J ) 7.9 Hz, 1H), 6.86 (d, J ) 7.9 Hz, 1H),
6.94 (s, 1H), 7.12-7.37 (m, 5H); 13C NMR 22.2 (CH3), 37.7 (CH2),
38.8 (CH2), 55.4 (CH), 109.1 (CH), 125.0-130.3 (CH and C),
137.6 (C), 149.3 (C); MS 249 (M+, 100), 234 (61), 130 (38), 117
(97), 91 (19). Exact mass calcd for C18H19N 249.1517, found
249.1515.
Su p p or tin g In for m a tion Ava ila ble: 1H NMR, 13C NMR,
and GC-MS spectra of compounds 1b,c, 1b-H, 1c-H, 2b,c, 3c,
4 (trans/cis), and 5 (trans/cis); relevant NOE effects for the
assignment of 4 (trans/cis) and 5 (trans/cis). This material is
tr a n s-2-Meth yl-4-p h en yl-1,2,5,6-tetr a h yd r o-4H-p yr r olo-
[3,2,1-ij]qu in olin e (tr a n s-4): FTIR 1601, 1471, 1365; 1H NMR
J O020355W
7918 J . Org. Chem., Vol. 67, No. 22, 2002