Imides Imines

Almost all organic functional groups except for olefinic double bonds are reduced by hthium aluminum hydride. It reduces acids, esters, acid chlorides, amides, imides, imines, nitriles, nitroorganics, epoxides, and lactones. 

Aromatic imines are usually intensely yellow. Other possible byproducts which may be formed in the polyimide system are the previously discussed isoimide and imide-imine formed by the following reaction. 

Acid/base stress testing is performed to force the degradation of a drug substance to its primary degradation products by exposure to acidic and basic conditions over time. Functional groups likely to introduce acid/base hydrolysis are amides (lactams), esters (lactones), carbamates, imides, imines, alcohols (epimerization for chiral centers), and aryl amines. 

Benzylideneanilines have been added across 2,3-dihydrofurans to produce bicyclic azetidines regio- and stereoselectively a zwitterionic mechanism is proposed. An extensive range of reaction parameters have been calculated for the Mannich reaction of benzoxazole with formaldehyde/dimethylamine. A molybdenum bis(imide) has been used to catalyse C=N bond formation in imine-imine metathesis reactions of synthetic interest the approach has been extended to alkylidene-imine, imide-imine, and imide-imide metatheses. 1-Substituted 1-phenyl-... 

Copper-catalyzed (stoichiometric or catalytic) at room temperature and weak base under air Wide scope of substrates alcohols, amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, phenols, pyrazinones, pyridones, purines, pyrimidines, sulfonamides, sulfinates, sulfoximines, thiols, thiourea, ureas, and sulfonylguanidines... 

Arylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate and either triethyl-amine or pyridine at room temperature in air. The reaction works for amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, pyrazi-nones, pyridones, purines, pyrimidines, sulfonamides, sulfinates, sulfoximines, ureas, alcohols, phenols, and thiols. It is also the mildest method for NIO-vinylation. The boronic acids can be replaced with siloxanes or starmanes. The mild condition of this reaction is an advantage over Buchwald-Hartwig s Pd-catalyzed cross-coupling. The Chan-Lam C-X bond cross-coupling reaction is complementary to Suzuki-Miyaura s C-C bond cross-coupling reaction. 

Radovic et al. (1996) investigated the effects of nitriding the surface on adsorption from solution. Reacting with ammonia at elevated temperatures introduced pyridine functional groups on carbon. Reaction at 200 °C forms amides, imides, imines, amines, and nitriles while reaction at 250 °C results in bonding of ammonia to the carbon double bonds (Vinke et al., 1994). The effects of nitriding (at 250 °C) were similar to that of oxidation. Nitriding also hindered the adsorption of benzoate and aliphatic anions, oxalate, and fumarate. 

Scheme 5.39 Compilation of BMS/DuPont examples (amides, imides, imines, ureas, sulfonamides and phenols).

Cyanopyridazines add ammonia, primary and secondary amines and hydroxylamine to give amidines or amidoximes. Substituted amides, thioamides and carboximidates can be also prepared. With hydrazine, 3-pyridazinylcarbohydrazide imide is formed and addition of methylmagnesium iodide with subsequent hydrolysis of the imine affords the corresponding pyridazinyl methyl ketone. 

Stable heterocyclic five-member azomethine imines, azolium fV-imides, tria-zolium and pyrazolidinium ylides 98H(49)587. 

Although the photodriven reactions of chromium carbene complexes with imines superficially resemble those of free ketenes, there are major differences. The optically active oxazolidine carbene (Table 5) gave excellent yields and high ee values when allowed to react with imidates, oxazines, thiazines, and... 

Phosphorus ylids also react in a similar manner with the C=0 bonds of ketenes/ isocyanates, and certain anhydrides and imides, the N=0 of nitroso groups, and the C=N of imines, for example. 

Cohen F, Overman LE (1998) Planar-chiral cyclopalladated ferrocenyl amines and imines as enantioselective catalysts for allylic imidate rearrangements. Tetrahedron Asymmetry 9 3213-3222... 

Diphenylcarbodi-imide reacts with ylides to give, in general, the iminophosphorane (86) and the imines (85). The latter usually react with a second mole of ylide to give the stable phosphoranes (87) although the imine (85 R = R = Ph) was isolated. Hydrolysis of the solution... 

The efficient conversion of the furazans (70) into 1,4-dinitriles (71) is thought to occur via the nitrile oxides (72). Thermal decomposition of the diaziridones (73) in the presence of triethyl phosphite gives the phosphine-imine (75) and the isocyanate (74), which subsequently react together to give the carbodi-imide (76). ... 

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