Jan-Feb 2003
Some Novel Annelated 1,2,3-Selena/Thiadiazoles and 2H-Diazaphospholes
151
Table 2
NMR Spectral Data of Compounds 2, 4 and 7 – 12
1
13
No.
H NMR (δ, ppm)
C NMR (δ, ppm)
2a
0.78 (d, 3H, CH , J=6.6 Hz), 1.75 (s, 1H, N-CH ), 2.55 (dd, 1H, H -5,
10.35 (CH ), 41.15 (NCH ), 49.52 (C ), 51.21 (C ), 70.26
3 3 5 3
3
3
eq
J= 14.8, 3.3 Hz), 2.82 - 2.93 (m, 2H, H -5 & H-3), 3.01 (d, 1H, H-2,
(C ), 77.88 (C ), 208.53 (C ).
ax
6 2 4
J=10.3 Hz) 3.43 (dd, 1H, H-6, J=14.5, 3.5 Hz), 7.24 -7.45 (m, 10H,
Ar-H).
2b
0.84 (d, 3H, CH , J=6.8 Hz), 1.73 (s, 1H, N-CH ), 2.61 (dd, 1H,
10.80 (CH ), 41.22 (NCH ), 49.18 (C ), 51.67 (C ), 55.34
3 3 5 3
3
3
H
-5, J= 14.5, 3.4 Hz), 2.81 (q, 1H, H-3), 2.94 (t, 1H, H -5), 3.08
(OCH ), 70.63 (C ), 78.02 (C ), 207.36 (C ).
eq
ax
3 6 2 4
(d, 1H, H-2, J=10.1 Hz) 3.49 (dd, 1H, H-6, J=14.2, 3.8 Hz), 3.80 (s,
3H, OCH ), 6.85-7.38 (m, 9H, Ar-H).
3
2c
4a
4b
4c
0.82 (d, 3H, CH , J=6.6 Hz), 1.76 (s, 1H, N-CH ), 2.56 (dd, 1H, H -5,
10.44 (CH ), 41.08 (NCH ), 49.35 (C ), 51.82 (C ), 70.38
3 3 5 3
3
3
eq
J= 14.7, 3.3 Hz), 2.80-2.91 (m, 2H, H-3 & H -5), 3.12 (d, 1H, H-2,
(C ), 77.64 (C ), 208.13 (C ).
ax
6 2 4
J=10.2 Hz) 3.56 (dd, 1H, H-6, J=14.4, 3.1 Hz), 7.06-7.43 (m, 9H, Ar-H).
1.04 (d, 3H, CH , J=6.9 Hz), 3.08 (dd, 1H, H -5, J= 14.3, 3.8 Hz), 3.21
12.48 (CH ), 50.87 (C ), 52.92 (C ), 60.70 (C ), 66.88 (C ),
3 3 5 6 2
3
eq
(q, 1H, H-3), 3.32 (t, 1H, H -5), 4.12 (d, 1H, H-2, J=9.4 Hz) 4.32 (dd,
209.75 (C ).
ax
4
1H, H-6, J=14.5, 3.6 Hz), 7.09-7.32 (m, 10H, Ar-H).
1.01 (d, 3H, CH , J=6.6 Hz), 2.97 (dd, 1H, H -5, J= 14.2, 3.6 Hz), 3.14
12.65 (CH ), 50.65 (C ), 52.49 (C ), 54.99 (OCH ), 61.85
3 3 5 3
3
eq
-3.30 (m, 2H, H-3 & H -5), 3.73 (s, 3H, OCH ), 4.07 (d, 1H, H-2,
(C ), 66.32 (C ), 208.98 (C ).
ax
3
6 2 4
J=9.2 Hz) 4.40 (dd, 1H, H-6, J=14.7, 3.8 Hz), 6.74-7.31 (m, 9H, Ar-H).
1.08 (d, 3H, CH , J=6.8 Hz), 3.04 (dd, 1H, H -5, J= 14.4, 3.7 Hz), 3.16
12.60 (CH ), 50.53 (C ), 52.73 (C ), 61.13 (C ), 65.92 (C ),
3
eq
3
3
5
6
2
-3.34 (m, 2H, H-3 & H -5), 4.10 (d, 1H, H-2, J=9.2 Hz) 4.43 (dd, 1H,
210.02 (C ).
ax
4
H-6, J=14.5, 3.6 Hz), 6.85-7.30 (m, 9H, Ar-H).
7a
7b
1.39 (d, 3H, CH , J=6.6 Hz), 1.89 (s, 3H, NCH ), 3.25 (d, 1H, H-6, J=9.6
17.58 (CH ), 39.45 (C ), 41.60 (NCH ), 70.14 (C ), 74.61
3 7 3 4
3
3
Hz), 3.62-3.67 (m, 1H, H-7), 4.57 (s, 1H, H-4), 7.23-7.44 (m, 10H, Ar-H).
1.33 (d, 3H, CH , J=6.8 Hz), 1.91 (s, 3H, NCH ), 3.32 (d, 1H, H-6,
(C ), 143.50 (C ), 152.56 (C ).
6 9 8
17.40 (CH ), 40.07 (C ), 41.68 (NCH ), 55.26 (OCH ), 69.73
3
3
3
7
3
3
J=9.5 Hz), 3.60-3.66 (m, 1H, H-7), 3.83 (s, 3H, OCH ), 4.48 (s, 1H,
(C ), 74.22 (C ), 145.03 (C ), 151.92 (C ).
3
4 6 9 8
H-4), 6.91-7.39 (m, 9H, Ar-H).
7c
8a
8b
8c
9a
1.42 (d, 3H, CH , J=6.6 Hz), 1.86 (s, 3H, NCH ), 3.20 (d, 1H, H-6, J=9.5
Hz), 3.57-3.64 (m, 1H, H-7), 4.51 (s, 1H, H-4), 7.02-7.41 (m, 9H, Ar-H).
17.32 (CH ), 39.71 (C ), 41.77 (NCH ), 69.48 (C ), 75.06
3 7 3 4
3
3
(C ), 142.62 (C ), 151.72 (C ).
6 9 8
1.45 (d, 3H, CH , J=6.8 Hz), 3.50-3.58 (m, 1H, H-7), 4.20 (d, 1H, H-6,
17.45 (CH ), 40.73 (C ), 59.21 (C ), 65.05 (C ), 144.23 (C ),
3 7 4 6 9
3
J=9.0 Hz), 4.60 (s, 1H, H-4), 7.11-7.36 (m, 10H, Ar-H).
151.43 (C ).
8
1.38 (d, 3H, CH , J=6.5 Hz), 3.46-3.52 (m, 1H, H-7), 3.78 (s, 3H, OCH ),
17.36 (CH ), 41.32 (C ), 54.86 (OCH ), 60.44 (C ), 65.56
3 7 3 4
3
3
4.26 (d, 1H, H-6, J=9.2 Hz), 4.66 (s, 1H, H-4), 6.80-7.28 (m, 9H, Ar-H).
(C ), 143.02 (C ), 153.08 (C ).
6 9 8
1.40 (d, 3H, CH , J=6.6 Hz), 3.52-3.59 (m, 1H, H-7), 4.21 (d, 1H, H-6,
17.52 (CH ), 40.98 (C ), 60.85 (C ), 64.88 (C ), 145.11 (C ),
3 7 4 6 9
3
J=9.0 Hz), 4.75 (s, 1H, H-4), 6.84-7.32 (m, 9H, Ar-H).
152.75 (C ).
8
1.25 (d, 3H, CH , J=6.5 Hz), 1.83 (s, 3H, NCH ), 3.18 (d, 1H, H-6,
16.73 (CH ), 40.22 (C ), 41.53 (NCH ), 69.86 (C ), 74.02
3 7 3 4
3
3
J=9.8 Hz), 3.55-3.62 (m, 1H, H-7), 4.51 (s, 1H, H-4), 7.25-7.51 (m,
(C ), 140.42 (C ), 151.56 (C ).
6 9 8
10H, Ar-H).
9b
1.22 (d, 3H, CH , J=6.6 Hz), 1.88 (s, 3H, NCH ), 3.23 (d, 1H, H-6,
16.58 (CH ), 39.29 (C ), 41.43 (NCH ), 56.12 (OCH ), 70.23
3 7 3 3
3
3
J=9.5 Hz), 3.48-3.56 (m, 1H, H-7), 3.77 (s, 3H, OCH ), 4.32 (s, 1H,
(C ), 74.61 (C ), 138.85 (C ), 150.83 (C ).
3
4 6 9 8
H-4), 6.80-7.37 (m, 9H, Ar-H).
9c
1.29 (d, 3H, CH , J=6.5 Hz), 1.85 (s, 3H, NCH ), 3.11 (d, 1H, H-6, J=9.7
17.04 (CH ), 39.86 (C ), 41.61 (NCH ), 69.92 (C ), 74.73
3 7 3 4
3
3
Hz), 3.54-3.60 (m, 1H, H-7), 4.40 (s, 1H, H-4), 6.96-7.42 (m, 9H, Ar-H).
(C ), 141.05 (C ), 150.27 (C ).
6 9 8
10a
10b
10c
11a
11b
1.31 (d, 3H, CH , J=6.6 Hz), 3.45-3.52 (m, 1H, H-7), 4.28 (d, 1H, H-6,
J=9.0 Hz), 4.73 (s, 1H, H-4), 7.18-7.44 (m, 10H, Ar-H).
17.01 (CH ), 39.86 (C ), 61.83 (C ), 67.13 (C ), 141.13 (C ),
3 7 4 6 9
3
150.21 (C ).
8
1.37 (d, 3H, CH , J=6.7 Hz), 3.41-3.47 (m, 1H, H-7), 3.74 (s, 3H, OCH ),
16.72 (CH ), 41.02 (C ), 55.80 (OCH ), 61.35 (C ), 66.48
3 7 3 4
3
3
4.20 (d, 1H, H-6, J=9.2 Hz), 4.82 (s, 1H, H-4), 6.92-7.35 (m, 9H, Ar-H).
(C ), 139.75 (C ), 151.14 (C ).
6 9 8
1.28 (d, 3H, CH , J=6.5 Hz), 3.38-3.44 (m, 1H, H-7), 4.36 (d, 1H, H-6,
17.35 (CH ), 40.71 (C ), 61.02 (C ), 66.64 (C ), 140.73 (C ),
3 7 4 6 9
3
J=8.9 Hz), 4.70 (s, 1H, H-4), 6.88-7.32 (m, 9H, Ar-H).
150.83 (C ).
8
1.31 (d, 3H, CH , J=6.4 Hz), 1.85 (s, 3H, NCH ), 3.20 (d, 1H, H-6, J=9.6
16.95 (CH ), 38.73 (C ), 41.67 (NCH ), 67.93 (C ), 75.22
3 7 3 4
3
3
Hz), 3.51-3.58 (m, 1H, H-7), 4.32 (s, 1H, H-4), 7.20-7.46 (m, 15H, Ar-H).
1.35 (d, 3H, CH , J=6.6 Hz), 1.78 (s, 3H, NCH ), 3.25 (d, 1H, H-6,
(C ), 148.35 (C ), 166.79 (C , J =52 Hz).
6 8 9 CP
17.14 (CH ), 39.31 (C ), 41.75 (NCH ), 55.62 (OCH ), 67.34
3
3
3
7
3
3
J=9.7 Hz), 3.45-3.50 (m, 1H, H-7), 3.72 (s, 3H, OCH ), 4.24 (s, 1H,
(C ), 74.86 (C ), 149.02 (C ), 164.55 (C , J =53 Hz).
3
4 6 8 9 CP
H-4), 7.06-7.42 (m, 14H, Ar-H).
11c
12a
12b
12c
1.33 (d, 3H, CH , J=6.4 Hz), 1.83 (s, 3H, NCH ), 3.28 (d, 1H, H-6, J=9.8
Hz), 3.44-3.49 (m, 1H, H-7), 4.35 (s, 1H, H-4), 6.92-7.40 (m, 14H, Ar-H).
16.78 (CH ), 39.38 (C ), 41.72 (NCH ), 66.88 (C ), 75.50
3 7 3 4
3
3
(C ), 148.27 (C ), 167.32 (C , J =50 Hz).
6 8 9 CP
1.36 (d, 3H, CH , J=6.6 Hz), 3.46-3.52 (m, 1H, H-7), 4.32 (d, 1H, H-6,
17.62 (CH ), 40.92 (C ), 60.84 (C ), 67.18 (C ), 149.23 (C ),
3 7 4 6 8
3
J=9.2 Hz), 4.72 (s, 1H, H-4), 7.10-7.43 (m, 15H, Ar-H).
164.95 (C , J =54 Hz).
9 CP
1.30 (d, 3H, CH , J=6.5 Hz), 3.50-3.56 (m, 1H, H-7), 3.70 (s, 3H, OCH ),
17.03 (CH ), 41.37 (C ), 55.83 (OCH ), 61.56 (C ), 66.94
3 7 3 4
3
3
4.25 (d, 1H, H-6, J=9.0 Hz), 4.67 (s, 1H, H-4), 6.98-7.42 (m, 14H, Ar-H).
(C ), 147.54 (C ), 166.87 (C , J =52 Hz).
6 8 9 CP
1.32 (d, 3H, CH , J=6.7 Hz), 3.43-3.50 (m, 1H, H-7), 4.21 (d, 1H, H-6,
17.75 (CH ), 41.03 (C ), 61.32 (C ), 67.54 (C ), 148.58 (C ),
3 7 4 6 8
3
J=9.0 Hz), 4.80 (s, 1H, H-4), 6.95-7.40 (m, 14H, Ar-H).
163.27 (C , J =53 Hz).
9 CP