Unusual Aminations with Tetramethylguanidine

Gabbutt, Christopher D.; Heron, B. Mark; McCreary, Janice M.; Thomas, David A.

doi:10.3184/030823402103171302

Cited by 6 publications

(2 citation statements)

References 17 publications

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“…Running the reaction at room temperature slightly lowers the yield from 93 to 84%. The high efficiency and mild reaction conditions for this overall transformation are of great importance, since o -(dimethylamino)aryl ketones are generally prepared through pathways involving harsh and regiorandom Friedel–Crafts reaction conditions or nucleophilic aromatic substitutions of o -fluoroaryl ketones, which are not very readily available, by amino or proamino nucleophiles. , …”

Section: Resultsmentioning

confidence: 99%

Synthesis ofo-(Dimethylamino)aryl Ketones, Acridones, Acridinium Salts, and 1H-Indazoles by the Reaction of Hydrazones and Arynes

Dubrovskiy

Larock

2012

J. Org. Chem.

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A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.

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Section: Resultsmentioning

confidence: 99%

Synthesis ofo-(Dimethylamino)aryl Ketones, Acridones, Acridinium Salts, and 1H-Indazoles by the Reaction of Hydrazones and Arynes

Dubrovskiy

Larock

2012

J. Org. Chem.

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“…The ability to synthesize the truxenones substituted by fluorine at positions 4, 9, and 14, combined with the fact that the carbonyl-substituted central ring activates aromatic nucleophilic substitution, − provides an alternative route for the preparation of the truxenones substituted by an amine donor group. We have realized the triple nucleophilic substitution of the 4,9,14-trifluorotruxenone with some secondary amines, including acyclic versions such as dibutylamine and dihexylamine as well as cyclic amines such as pyrrolidine and the chiral secondary amines l -(+)-prolinol and ( R )-(+)-3-pyrrolidinol.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Characterization of New Truxenones for Nonlinear Optical Applications

et al. 2006

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The synthesis of several new truxenones and one tris(dicyanomethylene) derivative substituted by different amines at positions 4, 9, and 14 is reported. A complete characterization of the NLO properties of representative derivatives was carried out by hyper-Rayleigh scattering; the major electronic effects and the influence of the structural modifications on the NLO properties have been examined. Because of their C 3 symmetry and their large first hyperpolarizability, the chiral versions of the tris(dicyanomethylene) truxene derivatives are of interest for second-order nonlinear optics in uniaxially aligned chiral media.

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