3 . The synthesis of this compound
3 has been
described before in the paper of [1].
The (1
S ,9a
R )-1-[(1,2,3-triazol-1-yl)methyl]octahydro-1
H -quinolizines of
7-9 have
been synthesized by the reaction of lupinine azide
3 with the terminal alkynes of 3-
(prop-2-yn-1-yl-thio)-1
H -1,2,4-triazol-5-amine
4 , (2
R ,2
S )-3-methylpent-4-yne-2,3-diol
5 and with aryloxymethyl-substituted 3-ethoxy-4-(prop-2-ynyloxy)benzaldehyde
6 under the reaction conditions of 1,3- dipolar cycloaddition. In addition, the (1
S ,9a
R )-1-
[(1,2,3-triazol-1-yl)methyl]octahydro-1
H -quinolizines of
7-9 have contained various
substituents at C-4 position of 1,2,3-triazole cycle (
Scheme 1 ).
Scheme 1. Synthesis of quinolizine-triazoles of
7-9 The structure of the synthesized compounds of
7-9 has been confirmed by IR-,
1
H-,
13
C- NMR spectroscopies and mass spectrometry. Compound
8 has been formed as a
mixture of (17ʹ
R ,17ʹ
S )-diastereomers (4:1, as in an original alkyne
5 ). The structure
8 has been determined by correlation of proton signals at C-19 atom, doublets of the C-22
methyl group and singlets of the C-21 methyl group.
References
1. Nurmaganbetov Zh.S., Savelyev V.A. et al., Synthesis and analgesic activity of 1-
[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine [J], Chem.
Heterocycl. Compd., 2021,
57 (9): 911-919.
N
N
N
N
S
N
HN
N
H
2
N
N
N
N
N
C
C
HO
H
OH
H
3
C
N
N
N
N
O
O
H
O
H
3
C
C
H
C
CH
3
OH
CH
3
S
N
NH
N
NH
2
O
O
H
O
CH
3
CuSO
4
.
5H
2
O,
DMF, 75
o
C
