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Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269
Graphical Abstract
Scheme 1: Conventional method of synthesis of thiazolidine-2,4-dione derivatives.
Scheme 2: [2 + 2 + 2] Cyclotrimerization of N-methylthiazolidinedione.
Scheme 3: Unexpected product 5b obtained in the attempted NH-protection of thiazolidinedione with (Boc)2O.
Figure 1: Comparison of 13C NMR values of 9 and 5b.
Scheme 4: [2 + 2 + 2] Cyclotrimerization of dipropargylthiazolidinediones with propargyl halides.
Scheme 5: Formation of sultine 13 from compound 8b followed by DA reaction.
Scheme 6: Dipropargylation of 2,4-thiazolidinedione derivatives.
Scheme 7: [2 + 2 + 2] Cycloaddition in the presence of Wilkinson’s catalyst.
Scheme 8: N-Ester derivative 18 hydrolysis to N-acid derivative 22.
Scheme 9: Synthesis of triazolo derivative 24 via click reaction.
Beilstein J. Org. Chem. 2015, 11, 1367–1372, doi:10.3762/bjoc.11.147
Figure 1: Structures of diverse biologically as well as theoretically interesting molecules.
Figure 2: Retrosynthetic analysis of bis-spiro-pyrano cage compound 7.
Scheme 1: Synthesis of hexacyclic cage dione 10.
Scheme 2: Synthesis of tetrahydrofuran-based cage compounds 12 and 13.
Figure 3: (a)Optimized structure of 12, (b) optimized structure of 13.
Scheme 3: Synthesis di-allyl cage compound 11.
Scheme 4: Synthesis of spiro-pyrano cage molecules 7 and 17.
Figure 4: (a) Optimized structure of 18, (b) optimized structure of 7.
Scheme 5: Synthesis of octacyclic cage compound 18 via intramolecular DA reaction.
Scheme 6: Attempted synthesis to cage compound 20.