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1 article(s) from Zhou, Garr-Layy

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

David R. Chisholm,
Garr-Layy Zhou,
Ehmke Pohl,
Roy Valentine and
Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

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Figure 1: Tetrahydroquinoline (THQ) and dihydroquinoline (DHQ) scaffolds to be synthesised.

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Scheme 1: Proposed retrosynthesis scheme to access N-isopropyl-THQ 2.

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Scheme 2: Synthesis of THQ 3 by initial N-alkylations, followed by PPA-mediated cyclisation.

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Scheme 3: Bromination of 3 and attempted halogen exchange of the intermediate 7.

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Scheme 4: Synthesis of THQ 10, by initial aza-Michael addition, followed by formation of the tertiary alcohol ...

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Scheme 5: Synthesis of THQ 14 by initial acylation, cyclisation with H₂SO₄ and reduction with borane·dimethyl...

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Scheme 6: N-Alkylation of 13 and 14.

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Scheme 7: Facile route for the synthesis of 20a.

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Scheme 8: Synthesis of THQ 21 and DHQ 22 using borane·dimethyl sulphide complex or DIBAL, respectively.

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Figure 2: Simulated structure of 22 indicates a flattened quinoline-like structure. Hartree–Fock calculations...

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Scheme 9: Postulated mechanism for the formation of 22 using DIBAL.

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Figure 3: Combined, normalised absorption and emission spectra of 28 in chloroform. Absorption spectrum was r...

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Scheme 10: Miyaura borylation of 21 and 22 to give crystalline boronic esters 29 and 30.

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Figure 4: Comparison of the crystal structures of 29 (left) and 30 (right) as viewed along the plane of the a...

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Figure 5: Combined, normalised absorption and emission spectra of 30 in diethyl ether. Absorption spectrum wa...

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Published 16 Aug 2016

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