4
N
Se
Si
N
S
N
O
S
N
Se
Si
S
N
S
N
Se
N
Se
N
O
Se
Scheme 6. Novel functionalized heterocycles and scaffolds for
organic synthesis and possible drug discovery.
Fig. 4. ORTEP molecular structure of compound 11b (recrystallized
from methanol).
Supplementary Material
The structural assignments of synthesized compounds were
1
Supplementary data including experimental section with
spectral data and single crystal X-ray crystallography data
(CCDC 1850211, 1850213, 1850214 and 1850212 for
compounds 5b, 10a,b and 11b, respectively) associated with this
article can be found, in the online version, at
made using single crystal X-ray diffraction analysis, H, 13C, 29Si
and 77Se NMR spectroscopy including two-dementional
homonuclear (2D COZY) and heteronuclear (2D HMBC, 2D
HSQC) methods. Good analytical data were obtained. The
compounds 9-14a,b have two stereocenters, however, the
condensed cycloalkane and tetrahydrofuran rings occur in cis-
configuration according to X-ray analysis (Fig. 3, 4) and NMR
data. The structure of the 2-substituted heterocycle 8b was
proved, inter alia, by measurement of the spin-spin coupling
constant of the selenium atom with the carbon atom of the CH
group (50.3 Hz), which corresponds to the direct coupling
constant (1JC-Se). This indicates the addition of the selenium atom
to the α-carbon atom of the vinyl group of tetravinylsilane. In the
case of 3-substituted derivatives, the direct coupling constants of
selenium atom with the carbon atom of the CH2 group were
observed (50-52.8 Hz).
References and notes
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Conclusions
Regioselective synthesis of a novel family of 2H,3H-
[1,3]thiazolo- and -selenazolo[3,2-a]pyridin-4-ium heterocycles
was developed based on 2-pyridinesulfenyl and selenenyl halides
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cycloalkenes). Noteworthy, the tricyclic scaffolds based on 2,3-
dihydrofuran and cycloalkenes were hitherto unknown (Scheme
6). The presence of functional groups (vinylsulfanyl,
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and synthesis of new derivatives. The reactions proceeded at
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The obtained compounds are water-soluble and this property
is favorable with respect to possible biological activity. The
obtained compounds represent novel functionalized heterocycles
and scaffolds for organic synthesis and possible drug discovery
(Scheme 6).
Acknowledgments
Financial support of Russian Science Foundation (Grant No
18-13-00372) is gratefully acknowledged. The authors thank
Baikal Analytical Center SB RAS for providing the instrumental
equipment for structural investigations.