Alkylation of Benzophenone with Aminoalkyl Halides in Liquid Ammonia

Anderson, Elvin L.; Casey, John E.

doi:10.1021/jo01022a520

Cited by 8 publications

(3 citation statements)

References 1 publication

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“…Generally speaking, the chemical behavior of the benzophenone anil adduct resembles that recently reported for the benzophenone ketyls (5)(6)(7)(8).…”

Section: Introductionsupporting

confidence: 79%

The Reactions of the Disodium Adduct of Benzophenone Anil

Smith¹,

Veach²

1966

Can. J. Chem.

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The disodium adduct of benzophenone anil has been treated with a variety of reagents, and the products have been isolated and identified. With alkyl halides, ethylene oxide, and diethyl sulfate, alkylation occurs a t the carbon atom. With tri-and tetra-methylene dibromide, nitrogen alkylation also occurs, thereby producing substituted pyrrolidine and piperidine derivatives. Benzaldehyde abstracts the allcali metal from the adduct whereas esters react to form the N-acyl derivatives.

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“…Generally speaking, the chemical behavior of the benzophenone anil adduct resembles that recently reported for the benzophenone ketyls (5)(6)(7)(8).…”

Section: Introductionsupporting

confidence: 79%

The Reactions of the Disodium Adduct of Benzophenone Anil

Smith¹,

Veach²

1966

Can. J. Chem.

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“…Clear evidences for the generation of diorganometallic compounds by the addition of alkali metals to carbon -oxygen double At variance with these results, the presence of a second aromatic ring on the carbonyl group stabilizes the ensuing carbanion, so that reduction of diaryl ketones (252) with alkali metals, affords stable solutions of the corresponding vic-diorganometals either in liquid ammonia or in ethereal solvents [139][140][141][142][143][144].…”

Section: Diaryl Ketonesmentioning

confidence: 99%

“…[141]; Ar = Ph, Ar' = 4-pyridyl, EX = 1 -(3-chloropropyl) -2 ,6-dimethylpiperidine, yield 77%, ref. [143] Scheme 65.…”

Section: Diaryl Ketonesmentioning

confidence: 99%

Benzylic Organometals via Reductive Metalation Procedures

Azzena¹,

Dettori²,

Pisano

2011

COC

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The review discusses two different reductive metalation approaches to the generation of benzylic organometals.In the first part, the scope of the generation of polar benzylic organometals by the reductive cleavage of carbon -heteroatom sigma bonds will be presented. Besides briefly showing the evolution of the technique, the review deals with recent achievements in the generation of benzylic derivatives of alkali metals by the reductive cleavage of carbon -halogen, carbon -oxygen, carbon -nitrogen and carbon -sulphur bonds. Significant synthetic applications of this procedure are described, showing that an appropriate choice of reaction conditions (solvent, temperature, alkali metal, employment of an electron shuttle) strongly affects the outcome of the cleavage reaction.In the second part, the application of the reductive metalation to carbon -carbon, carbon -oxygen and carbon -nitrogen double bonds is described, a procedure leading to the generation of vic-diorganometallic derivatives. Synthetic applications of these diorganometals are illustrated, underlining the possible application of 1,2-diarylsubstituted vic-dicarbanions as synthetic analogues of an activated form of an alkali metal that, however, function under homogeneous and mild reaction conditions.

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Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2

Hudgens

Taylor

Batts

et al. 2006

Bioorganic & Medicinal Chemistry

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The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [ 3 H]-BTX binding site and sodium currents of hNa v 1.2. Our lead compound (6), containing a diphenyl amine motif demonstrated a 53.2% inhibitory block of Na v 1.2 current at 10 μM, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNa v 1.2 activity and modification of the amine portion is detrimental to sodium channel block.

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Alkylation of Benzophenone with Aminoalkyl Halides in Liquid Ammonia

Cited by 8 publications

References 1 publication

The Reactions of the Disodium Adduct of Benzophenone Anil

The Reactions of the Disodium Adduct of Benzophenone Anil

Benzylic Organometals via Reductive Metalation Procedures

Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2

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