Amines parent hydrides

In the names of amines, the general use of suffixes and prefixes is not always observed. Normally, the suffix -amine would be added to the name of the parent hydride and engender names such as methanamine (CH3-NH2). Further substitution on the nitrogen atom would then be indicated by prefixes, leading to names that appear very cumbersome, such as A -methylmethanamine for (CH3)2NH and N,N-dimethylmethanamine for (CH3)3N. The traditional names of methylamine, di-methylamine and trimethylamine are much simpler. In these names, the term amine is not a suffix. It is, in fact, the name of the parent hydride, NH3, which now serves as the basis of substitutive names. Names such as diethylamine and tributylamine are representative of the preferred nomenclature. Diamines are named accordingly, as with ethane-1,2-diamine for H2N-CH2-CH2-NH2 and propane-1,3-diamine for H2N-[CH2]3-NH2. There are allowed alternatives for these last two compounds ethylenediamine and propane-1,3-diyldiamine. 

NH3 NHj, azane (parent hydride name), amine (parent name for certain organic derivatives), trihydridonitrogen ammonia NHj", azaniumyl, trihydridonitrogen) 1 +) -NHj azaniumyl ammonio azanuidyl, trihydridonih ate( 1—) NH, ammine... 

Secondary and tertiary amines are in most cases still named radicofunc-tionally, in a manner that can easily be transformed into a substitutive naming mode based on the parent hydride name azane. Within the boundaries of conventional substitutive nomenclature, amines of that sort are interpreted as products of N-substitution of the most serior primary amine present. 

Acylation of norephedrine (56) with the acid chloride from benzoylglycolic acid leads to the amide (57), Reduction with lithium aluminum hydride serves both to reduce the amide to the amine and to remove the protecting group by reduction (58), Cyclization by means of sulfuric acid (probably via the benzylic carbonium ion) affords phenmetrazine (59), In a related process, alkylation of ephedrine itself (60) with ethylene oxide gives the diol, 61, (The secondary nature of the amine in 60 eliminates the complication of dialkylation and thus the need to go through the amide.) Cyclization as above affords phendimetra-zine (62), - Both these agents show activity related to the parent acyclic molecule that is, the agents are CNS stimulants... 

Hydrazones treated with alkalis decompose to nitrogen and hydrocarbons [845, 923] Woljf-Kizhner reduction) (p. 34), and p-toluenesulfonylhydra-zones are reduced to hydrocarbons by lithium aluminum hydride [812], sodium borohydride [785] or sodium cyanoborohydride [813]. Titanium trichloride hy-drogenolyzes the nitrogen-nitrogen bond in phenylhydrazones and forms amines and ketimines which are hydrolyzed to the parent ketones. Thus 2,4-dinitrophenylhydrazone of cycloheptanone afforded cycloheptanone in 90% yield [202]. 

Known examples of N—H oxidative addition prior to 1980 usually involved the addition of relatively acidic N—H bonds, for example that in phthalimide, to Pd(0) or Pt(0) centres. Work by Milstein in the 1980s showed that the parent amine NH3 can oxidatively add to Ir(I) centres (see Section 6.2.4) under mild conditions to afford parent amido hydrides in good... 

The cyclization can be carried out with halogenated amines, and substitution products of the new ring systems can also be obtained in the conventional way, by nitration, etc. Similar compounds can be prepared directly by using arylboron dichlorides in place of boron trichloride in the procedure indicated above. The parent borazarene derivatives, with hydrogen attached to boron, can be made from the B-hydroxy compounds with lithium aluminum hydride in the presence of aluminum chloride. N-Alkyl derivatives can be made either by using N-alkyl derivatives of the aminobiphenyls as starting materials, or by N-alkylation of the unsubstituted compounds via their N-lithio derivatives. Apart from their inherent interest, compounds of this type can serve as intermediates in various syntheses. Thus benzocinnolines and 2,2 -dihydroxybiphenyls can be obtained from derivatives of 2-aminobiphenyl. ... 

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