Reductive of amines

Fuxe K, Andersson K, Nilsen OG, et al Toluene and telencephalic dopamine selective reduction of amine mrnover in discrete DA nerve terminal systems of the anterior caudate nucleus by low concentrations of toluene. Toxicol Lett 12 115—123,1982 Cause EM, Mendez V, Geller I Exploratory smdies of a rodent model for inhalant abuse. Neurobehav Toxicol Teratol 7 143—148, 1985 Gentry JR, Hill C, Malcolm R New anticonvulsants a review of applications for the management of substance abuse disorders. Ann Clin Psychiatry 14 233—245, 2002 Gerasimov MR, Ferrieri RA, Schiffer WK, et al Smdy of brain uptake and biodistribution of [llCjtoluene in non-human primates and mice. Life Sci 70 2811 — 2828, 2002... 

TABLE 21. ORGANOSILANE REDUCTION OF AMINALS AND HEMIAMINALS (Continued)... 

Supplemental Reference for Table 21. Organosilane Reduction of Aminals and Hemiaminals... 

Unsymmetrical secondary aliphatic amines have been prepared by reaction of alkyl halides with benzylidene amines and subsequent hydrolysis 814 by reaction of alkyl halides with alkyl amines 5 by reduction of amine-aldehyde adducts 8-8 and by dealkylation of tertiary amines with dibenzoyl peroxide. ... 

To circumvent this problem, several methods have been developed (157). Probably, the most prominent method is treatment with sodium boro-hydride (0.1% in PBS, 30 minutes prior to staining). NaBILi is known to neutralize Schiff s bases through reduction of amine-aldehyde compounds into nonfluorescent salts. 

Reduction of Amine Oxides and Azoxy Compounds /V-Oxy gen-detachment... 

Oxidative cleavage of amines 9-39 Reduction of amides 9-47 Reduction of nitro compounds 9-50 Reduction of nitroso compounds or hydroxylamincs 9-51 Reduction of oximes 9-52 Reduction of azides 9-53 Reduction of isocyanates, isothiocyanates, or N-nitroso compounds 9-55 Reduction of amine oxides 9-59 Reduction of azo, azoxy, or hydrazo compounds... 

Reduction of amines. Birch13 noted that N,N-dimethylaniIines are reducible by lithium and liquid ammonia, but Stork and White14 made the more significant observation that the primary amine precursors of the tertiary amines are also reducible in satisfactory yields. In a careful study of the reduction of o-toluidine. the highest yields were obtained with the combination lithium-liquid ammonia-/-butanol. One advantage of using an amine as substrate is that the unreduced basic amine is readily separated from neutral ketonic products. In all cases examined the desired unsatura-... 

The present Section deals with reductive alteration of a nitrogenous group without formation of an N-H bond, e.g., reduction of amine oxides and azoxy compounds. 

Reduction of amine oxides affords the tertiary amines in a very pure state. Jerchel and Melloh170 have described the isolation of pure methylpyridines from methylpyridine mixtures by way of the N-oxides. 

The introduction of CN into the aniline molecule would be expected to reduce the nucleophilicity of NH2 and from the para position this should be more or less according to the Gp of CN. There is plenty of information regarding the analogous effect of /7-NO2, but examples involving CN are hard to find. It is easy, however, to find an example for the reduction of amine nucleophilicity by the +/effect of CN. Grob and Schlageter have presented extensive results for the quaternization of 4-X-substituted quinuclidines (c/ structure 7) with methyl iodide in methanol at 10.0 °C. According to Charton, the pj constant for this reaction is -1.12, and the log k values for X = H and CN are - 2.35 and... 

A number of tricyclic heterosystems have been synthesized from nitroindoles and nitroindazoles [46, 47]. In these transformatirms the vicarious amination of bicyclic compounds 43 at the ort/to-position relative to the nitro group proved to be the key step. 1,1,1-TrimethyUiydrazonium iodide (TMHI) was used as the VNS-aminating agent (Scheme 24). Reduction of amines 44 followed by heterocy-clization resulted in the formation of various types of heterocycles 45-48. 

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