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2 article(s) from Laali, Kenneth K

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

Rodrigo Abonia,
Luisa F. Gutiérrez,
Braulio Insuasty,
Jairo Quiroga,
Kenneth K. Laali,
Chunqing Zhao,
Gabriela L. Borosky,
Samantha M. Horwitz and
Scott D. Bunge

Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60

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Scheme 1: Representative examples of tris(hetero/aryl)methanes, molecular hybrids and bis(indolyl)methanes wi...

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Scheme 2: Previous synthetic approaches for the synthesis of triarylmethane analogues in comparison to the pr...

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Scheme 3: Synthesis of the starting N-alkylindoles 1{4–10}.

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Scheme 4: General procedure for the synthesis of the starting quinoline-/quinolone aldehydes 6{1–7}.

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Scheme 5: Chemset of coumarins 7{1–4} for elaboration in the MCR experiments.

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Scheme 6: Exploratory reaction leading to isolation of products 8{1,1,1} and 9{1,1,1}.

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Figure 1: Pseudo-three-component synthesis of bisindole triads 8 employing quinoline-/quinolone-CHO 6{1–6}, c...

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Scheme 7: Chemset of further aldehydes 6{8–10} for elaboration in the MCR experiments.

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Figure 2: Three-component synthesis of tris(heteroaryl)methane triads 9. ^aThis product was obtained as an ins...

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Figure 3: Thermal ellipsoid plot (40% probability level) of the tris(heteroaryl)methane triad 9{4,7,1}.

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Figure 4: DFT-optimized structure of 9{4,7,1} triad.

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Scheme 8: Synthesis of crowed (Het¹₂Het²/Ar²)C⁺PF₆⁻ salts 10.

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Figure 5: 1D- and 2D-based NMR assignments for methylium-PF₆ salt 10{4,4,8}.

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Figure 6: 1D- and 2D-based NMR assignments for methylium-PF₆ salt 10{4,4,11}.

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Figure 7: Optimized geometry of methylium-PF₆ salts 10{4,4,8}.

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Figure 8: Optimized geometry of methylium-PF₆ salt 10{4,4,11}.

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Published 12 Mar 2019

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Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH₄SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition

A. Srinivas Reddy and
Kenneth K. Laali

Beilstein J. Org. Chem. 2015, 11, 1641–1648, doi:10.3762/bjoc.11.180

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Scheme 1: Reaction of benzyl allenoate (1) with TMSBr with and without Selectfluor (E/Z designations, as illu...

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Scheme 2: Reaction of benzyl allenoate (1) with TMSBr with and without Selectfluor in IL solvents (E/Z design...

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Scheme 3: Reaction of benzyl allenoate (1) with TMSI and TMSCl, with and without Selectfluor (E/Z designation...

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Scheme 4: Reaction of benzyl allenoate (1) with NH₄SCN/Selectfluor in different solvents (E/Z designations, a...

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Figure 1: Allene esters synthesized for this study.

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Scheme 5: Reaction of ethyl allenoate (2) with TMSX/Selectfluor and NH₄SCN/Selectfluor (E/Z designations, as ...

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Scheme 6: Reaction of ethyl allenoate 3 with TMSX/Selectfluor and NH₄SCN/Selectfluor (E/Z designations, as il...

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Scheme 7: Reaction of benzyl allenoate 4 with TMSX (X = Br, and Cl)/Selectfluor and NH₄SCN/Selectfluor (E/Z d...

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Scheme 8: Reaction of ethyl allenoate 5 with TMSI/Selecfluor in DMF and MeCN as the solvents (E/Z designation...

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Scheme 9: Reaction of benzyl allenoate 6 with NH₄SCN in presence and absence of Selectfluor.

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Scheme 10: Influence of allenoate structure.

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Published 16 Sep 2015

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Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH4SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition

Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH₄SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition