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Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96
Graphical Abstract
Figure 1: Known biologically active bicyclo[3.2.1]octenes/octadienes.
Figure 2: Previously prepared bicyclo[3.2.1]octenes/octadienes with cholinesterase inhibitory properties.
Scheme 1: Synthesis of annulated furobenzobicyclo[3.2.1]octadiene compounds.
Scheme 2: Synthesis of annulated thiophenebicyclo[3.2.1]octadiene compounds 8-10.
Scheme 3: Synthesis of compound 11.
Figure 3: 1H NMR spectra (CDCl3) for the trans-isomers 3–6.
Figure 4: UV spectra in ethanol (95%) of the cis- and trans-isomers of compound 3.
Figure 5: Photolysis spectra of cis-3 (a) and trans-3 (b) in ethanol (95%).
Figure 6: UV spectra in ethanol (95%) of the trans-isomers of compounds 3–7.
Figure 7: Molecular structure of compound trans-6. Displacement ellipsoids are drawn for the probability of 3...
Figure 8: Crystal packing of trans-6. (a) Chain parallel to [100] and (b) chain parallel to [010].
Figure 9: 1H NMR spectra (CDCl3) of compounds 1, 8, and 9.
Scheme 4: Synthesis of compound 12.
Figure 10: UV spectra of compounds 1 and 12 in ethanol (95%).
Figure 11: Photolysis spectra of compound 12 in ethanol (95%).
Scheme 5: Possible outcomes of future photocatalytic oxygenation reactions of new benzobicyclo[3.2.1.]octadie...
Beilstein J. Org. Chem. 2011, 7, 1663–1670, doi:10.3762/bjoc.7.196
Figure 1: Resonance structures of the sydnone ring.
Scheme 1: Thermal and photochemical intermolecular [3 + 2] cycloadditions.
Figure 2: Illustration of intramolecular [3 + 2] cycloadditions.
Figure 3: Styryl-sydnone 1 and stilbenyl sydnone 2 and their photoproducts F and G, respectively; target mole...
Scheme 2: Synthesis of the target molecules 3a and 3b.
Scheme 3: Photolysis of cis- or trans-3.
Scheme 4: Aromatization with DDQ.
Scheme 5: Possible mechanism for the formation of the photoproducts.
Scheme 6: Thermal reaction of trans-3.
Figure 4: ORTEP of compound 14.
Scheme 7: Thermal reaction of cis-3.
Figure 5: Proposed stereochemical pathway of sydnone ring (CH–N) and trans- and cis-stilbene (α–β).
Figure 6: Proposed stereochemical pathway of sydnone ring (N–CH) and trans- and cis-stilbene (α–β).
Scheme 8: Possible formation of thermal products 14 (from trans-3) and 15 (from cis-3).