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1 article(s) from Willis, Anthony C

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

Alireza Shakoori,
John B. Bremner,
Mohammed K. Abdel-Hamid,
Anthony C. Willis,
Rachada Haritakun and
Paul A. Keller

Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54

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Scheme 1: The synthesis of N-monoallylated indigo derivatives.

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Scheme 2: The synthesis of 8a-hydroxyazepinodiindolones.

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Figure 1: The structure and X-ray crystal structure (ball and stick representation) of azepinodiindolone 7. T...

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Figure 2: Dihydroazepino[1,2-a:3,4-b']diindolones from N_b-acyl-L-tryptophanamides [5].

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Scheme 3: The optimal synthesis of spiro heterocycles 12–16, and spiro/polyfused ring heterocycles 17 and 18 ...

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Scheme 4: The synthesis of the oxa-bridged azepinodiindolone 22 from indigo and 1-bromo-3-methylbut-2-ene.

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Figure 3: Modelled structure (Spartan 10, v1.1.0, Wavefunction Inc) of bridged indigo-tetrahydrofuran product ...

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Scheme 5: The reaction of indigo with cinnamyl bromide yielding two spiro-based derivatives.

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Figure 4: Structural analysis of compound 23. Left: modelled structure showing the cisoid configuration of th...

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Scheme 6: Proposed mechanism for the synthesis of the red diindolone heterocycles and the azepinodiindolones.

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Scheme 7: Proposed mechanism for the formation of 22. The order of protonation and allylation is undetermined....

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Scheme 8: Proposed mechanism for the formation of 23 from intermediate 29.

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Scheme 9: Proposed key branch points and mechanistic sinks in the base-catalysed cascade allylation reactions...

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Scheme 10: Reaction of the spiro heterocycle 12 with Grubbs' II catalyst, and X-ray crystal structure of the n...

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Published 15 Apr 2015

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