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Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174
Graphical Abstract
Figure 1: Tetrahydroquinoline (THQ) and dihydroquinoline (DHQ) scaffolds to be synthesised.
Scheme 1: Proposed retrosynthesis scheme to access N-isopropyl-THQ 2.
Scheme 2: Synthesis of THQ 3 by initial N-alkylations, followed by PPA-mediated cyclisation.
Scheme 3: Bromination of 3 and attempted halogen exchange of the intermediate 7.
Scheme 4: Synthesis of THQ 10, by initial aza-Michael addition, followed by formation of the tertiary alcohol ...
Scheme 5: Synthesis of THQ 14 by initial acylation, cyclisation with H2SO4 and reduction with borane·dimethyl...
Scheme 6: N-Alkylation of 13 and 14.
Scheme 7: Facile route for the synthesis of 20a.
Scheme 8: Synthesis of THQ 21 and DHQ 22 using borane·dimethyl sulphide complex or DIBAL, respectively.
Figure 2: Simulated structure of 22 indicates a flattened quinoline-like structure. Hartree–Fock calculations...
Scheme 9: Postulated mechanism for the formation of 22 using DIBAL.
Figure 3: Combined, normalised absorption and emission spectra of 28 in chloroform. Absorption spectrum was r...
Scheme 10: Miyaura borylation of 21 and 22 to give crystalline boronic esters 29 and 30.
Figure 4: Comparison of the crystal structures of 29 (left) and 30 (right) as viewed along the plane of the a...
Figure 5: Combined, normalised absorption and emission spectra of 30 in diethyl ether. Absorption spectrum wa...