1H and 13C NMR Study of Indoloquinolizines obtained from tryptamine and acetylacetaldehyde.

Results and Discussion

Carbon NMR Results

We assigned unambiguously the peaks corresponding to the methyl, methylene, methine and quaternary carbons by the complete decoupling (COM) and distortionless enhancement by polarization transfer (DEPT) methods. The assignments of the methyl, methylene and methine carbons were confirmed by the proton-detected heteronuclear multiple quantum coherence (HMQC) measurements[9], using correlation peaks with protons whose positions were established by the 1H NMR spectra.

The quaternary carbons were assigned by the proton-detected heteronuclear multiple bond connectivity (HMBC) experiment[10]. The results are summarized in table II.

13C NMR chemical shift data in DMSO-d6
A Indole
Tryptamine
Tryptamine.HCl
5
6
B
RESET
122.74 122.42 1
142.88 132.11 2
130.64 130.62 3
146.92 139.78 4
3''-CH2- 42.64 39.23 54.98 127.55 6
3'-CH2- 29.45 22.95 18.86 116.51 7
3 100.84 112.50 109.48 119.56 123.85 7a
3a 127.47 127.26 126.75 124.55 120.58 7b
4 119.87 118.23 118.05 120.85 122.24 8
5 118.64 117.99 118.35 120.92 121.79 9
6 120.75 120.69 121.03 126.97 129.89 10
7 111.26 111.21 111.48 112.73 112.90 11
7a 135.70 136.19 136.23 139.90 141.64 11a
2 125.07 122.46 123.22 124.59 129.57 12a
157.03 146.10 12b
21.82 21.42 2'-CH3
196.26 197.08 3'-C=O
29.33 29.43 3''-CH3
13C NMR chemical shift data in DMSO-d6 (cont.)
A 7
9
10
11
B
RESET
123.14 112.51 122.12 121.67 1
141.43 127.74 141.20 152.13 2
136.33 113.25 135.92 135.34 3
142.48 147.52 139.93 140.89 4
3''-CH2- 54.92 49.50 123.05 55.95 6
3'-CH2- 18.82 20.05 117.19 21.21 7
3 117.32 110.30 124.51 113.43 7a
3a 124.66 125.70 123.88 133.25 7b
4 120.55 118.59 120.24 120.24 8
5 120.50 119.15 119.71 119.76 9
6 126.04 122.86 126.71 123.06 10
7 112.56 111.27 117.19 117.26 11
7a 139.29 137.30 142.10 149.19 11a
2 124.56 127.20 129.36 128.41 12a
155.88 134.41 156.08 153.79 12b
20.70 96.03 22.00 21.26 2'-CH3
106.43 194.07 198.29 107.55 3'-C=O
25.49 26.65 30.03 26.66 3''-CH3
64.20 64.97 CH2-O-
CH2-O-
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