Mannich reactiohs of aryltrialkylstannunes in aprotic solvents

Cooper, Mark S.; Fairhurst, Robin A.; Heaney, H.; Papageorgiou, George; Wilkins, Robert H.

doi:10.1016/0040-4020(89)80024-9

Cited by 22 publications

(8 citation statements)

References 49 publications

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“…9 A number of methods have been developed for the generation of such intermediates, the best known of which is Eschenmoser's salt, which can be formed conveniently in aprotic solvents from N,N,N′,N′tetramethyldiaminomethane. [10][11][12][13] Komissarov has reported that aminals derived from aromatic aldehydes can be condensed with phenylacetylene and Cu(I) halides in acetonitrile to give propargylamines in good yields. 14,15 Under similar conditions, as shown in Table 1 (condition A), the reaction of 1,1-bis-(dialkylamino)-2,2,2-trifluoroethanes with arylacetylenes proceeded adequately, but considerably slower than the analogous reactions with nonfluorinated aminals.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane

2000

J. Org. Chem.

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Lewis acid-catalyzed deamination of aminal, 1,1-bis(dimethylamino)-2,2,2-trifluoroethane, using ZnI2 in ether, generates the 2,2,2-trifluoro-1,1-dimethylaminoethyl carbocation, which undergoes synthetically useful electrophilic reactions with alkynes, a variety of electron-rich alkenes, and TMS cyanide to form trifluoromethylated alkynylamines, homoallylic amines, alpha,beta-unsaturated ketones, and cyanoamines in fair to good yields.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane

2000

J. Org. Chem.

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“…N ‐(4‐Methoxybenzyl)morpholine: 16 Method A, colorless oil, yield (GC): 38%. − 1 H NMR (400 MHz, CDCl 3 ): δ = 2.40 (t, 3 J = 4.4 Hz, 4 H, 2 × CH 2 ), 3.43 (s, 3 H, CH 3 ), 3.68 (t, 3 J = 4.4 Hz, 4 H, 2 × CH 2 ), 3.78 (s, 2 H, CH 2 ), 6.85, 7.23 (m, 4 H, Ph).…”

Section: Methodsmentioning

confidence: 99%

Catalytic Amination of Aldehydes to Amides

2001

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Aldehydes react in a disproportionation reaction in the presence of rhodium catalysts to yield amines and amides. By adding N‐methylmorpholine N‐oxide as an oxidant in the presence of catalytic amounts of rhodium, the oxidative amination of aldehydes proceeds selectively to give the corresponding amide. Both aliphatic and aromatic aldehydes react with secondary amines to yield carboxylic acid amides in good to excellent yields.

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“…Reaction 10 of excess (CH 3 ) 2 NH in Et 2 O with 4.8 g (26 mmol) of 2-phenethyl bromide afforded 3.67 g (95%) of colorless oily N , N -dimethyl-2-phenethylamine: 1 H (cf. ref ); 13 C. By the procedure used for 20 , a solution of 2.00 g (13.4 mmol) of this amine and 1.83 g (13.4 mmol) of 15 in 20 mL of 1,2-dichloroethane gave, after recrystallization from EtOH, 1.46 g (38%) of colorless 32 : mp 274−275 °C; 1 H; 13 C; C, H, N.…”

Section: Methodsmentioning

confidence: 99%

Zwitterionic Sulfobetaine Inhibitors of Squalene Synthase

et al. 1999

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A substantial number of sulfobetaines (e.g., 10) have been synthesized and evaluated as inhibitors of squalene synthase (SS) on the basis of the idea that their zwitterionic structure would have properties conducive both to binding in the active site and to passage through cell membranes. When the simple sulfobetaine moiety is incorporated into compounds containing hydrophobic portions like those in farnesyl diphosphate (1) or presqualene diphosphate (2), inhibition of SS in a rat liver microsomal assay was indeed observed. For example, farnesylated sulfobetaine 10 has IC(50) = 10 &mgr;M and aromatic derivative 35 has IC(50) = 2 &mgr;M for SS inhibition. A wide variety of structural modifications, exemplified by compounds 43, 52, 76, 85, 91, 99, 111, and 115, was investigated. Unfortunately, no inhibitors in the submicromolar range were discovered, and exploration of a different type of zwitterion seems necessary if this appealing approach to inhibition of SS is going to provide a potential antihypercholesterolemic agent.

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Mannich reactiohs of aryltrialkylstannunes in aprotic solvents

Cited by 22 publications

References 49 publications

Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane

Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane

Catalytic Amination of Aldehydes to Amides

Zwitterionic Sulfobetaine Inhibitors of Squalene Synthase

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