A study of the reaction products from epichlorohydrin and aromatic amines

A method of preparing N-phenyl-3-hydroxy-1, 2, 3, 4-tetrahydroquinoline is developed, and some of its conversion products are obtained. The structures of N-phenyl-3-chloro-1, 2, 3, 4-tetrahydroquinoline and N-phenyl-1, 2, 3, 4-tetrahydroqunoline. are proved, the latter being formed by heating N-phenyl-3-hydroxy-1, 2, 3, 4-tetrahydroquinoline with concentrated hydrochloric acid.     

Investigation of the products of reaction of epichlorohydrin with aromatic amines

It is shown that the reaction of thionyl chloride with 1, 2, 3, 4-tetrahydro-3-hydroxy-6-methyl[h]benzoquinoline leads not only to aromatization of the tetrahydroquinoline ring, but also to chlorination of the methyl group.For Part II see [3].     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

4-Hydroxy- and 4-oxo-1,2,3,4-tetrahydrobenzo[h]quinolines were synthesized. Benzo[h]-quinoline, 1,2,3,4-tetrahydrobenzo[h]quinoline, and a dimeric compound are formed when the 4-hydroxy derivative is heated with hydrochloric acid or without it. The reaction of 4-hydroxy-1,2,3,4-tetrahydrobenzoth]quinoline with thionyl chloride was carried out.See [1] for communication X.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 548–551, April, 1972.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

The synthesis of 2-(hydroxymethyl)benz [g]indoline derivatives by heating N-acyl derivatives of 2-(chloromethyl)benz[g]indoline in dimethyl sulfoxide is described. 3,6-Dichloro-1,2,3,4-tetrahydrobenzo[h]quinoline, 5-chloroazirido[1,2-a]benz[g]indoline, and derivatives of 2-substituted 5-chlorobenz [g]indoline were synthesized.See [1] for communication XITranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1111–1116, August, 1972.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

The ethyl group of 3-hydroxy-6-ethyl-1,2,3,4-tetrahydrobenzo[h]quinoline is chlorinated and the tetrahydropyridine ring is aromatized under the influence of thionyl chloride. The corresponding 6-alkylbenzo[h]quinolines and 6-alkyl-1,2,3,4-tetrahydrobenzo[h]quinolines are formed when 3-hydroxy-6-alkyl-1,2,3,4-tetrahydrobenzo[h]quinolines are heated with polyphosphoric acid at 200–205°C, but only 6-alkylbenzo[h]quinolines are formed at up to 270°.See [1] for communication VIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1403–1406, October, 1971.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

N-(-Chloro--hydroxy)propyl derivatives of 5-chloro-1-naphthylamine, 8-chloro-1-naphthylamine, and 5-cyano-1-naphthylamine were obtained. They were cyclized to 1,2,3,4-tetrahydro-3-hydroxy-7-chlorobenzo[f]quinoline (II), 1,2,3,4-tetrahydro-3-hydroxy-10-chlorobenzo-[fJquinoline (VII), and 1,2,3,4-tetrahydro-3-hydroxy-7-cyanobenzo[f]quinoline (X). Chlorination at the 6 position to form 1,2,3,4-tetrahydro-3-hydroxy-6,7-dichlorobenzo[f]quinoline occurs under the action of thionyl chloride on II at room temperature. The action of thionyl chloride on II, VII, and X at elevated temperatures leads not only to chlorination at the 6 position but also to aromatization of the tetrahydropyridine ring to form, respectively, 6,7-dichlorobenzo[f]quinoline (V), 6,10-dichlorobenzo[f]quinoline (VIII), and 6-chloro-7-cyanobenzo[f]quinoline (XIII).See [5] for Communication V.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1522–1525, November, 1970.     

Investigations of the products of the reaction of epichlorohydrin with aromatic amines

Heating 3-hydroxy-1,2,3,4-tetrahydrobenzo[h]quinoline with phosphorus oxychloride gave a mixture of isomeric 3-chloro-1,2,3,4-tetrahydrobenzo[h]quinoline and 2-(chloromethyl)-benz[g]indoline, which are converted to a mixture of 3-benzoyloxy-1,2,3,4-tetrahydrobenzo-[h]quinoline and 2-(benzoyloxymethyl)benz[g]indoline on reaction with potassium benzoate. Saponification of 2-(benzoyloxymethyl)benz[g]indoline gave 2-(hydroxymethyl)benz[g]indoline. The reaction of the isomeric chloro derivatives with potassium cyanide gave 2-(benz[g]-indolinyl)acetonitrile.See [1] for communication IX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 362–366, March, 1972.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

The action of hydrogen halides on 7a,8-dihydro-7H-azirino[1,2-]benz[g]indole gives 2-halomethyl-2,3-dihydro-1H-benz[g]indoles and 3-halo-1,2,3,4-tetrahydrobenzo[h]quinolines, which were converted to the corresponding N-nitroso derivatives and then to the isonitroso derivatives. 2-(Benzoxymethyl)-2,3-dihydro-1H-benz[g]indole hydrohalides were obtained by heating 1-benzoyl-2-halomethyl-2,3-dihydro-1H-benz[g]indoles. The reaction of 3-halo-1,2,3,4-tetrahydrobenzo[h]quinolines with thionyl chloride at room temperature gives 3-halo-6-chloro-1,2,3,4-tetrahydrobenzo[h]quinolines, while refluxing with thionyl chloride gives 6-chlorobenzo[h]quinoline.See [1] for communication XVI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 342–346, March, 1973.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

A relatively simple method is proposed for the preparation of 4-hydroxyquinoline derivatives from the corresponding 4-oxo-1,2,3,4-tetrahydroquinoline derivatives. 4-Hydroxy-6-chloro-1,2,3,4-tetrahydrobenzo[h]quinoline is readily converted to a mixture of 6-chlorobenzo[h]-quinoline and 6-chloro-1,2,3,4-tetrahydrobenzo[h]quinoline.See [1] for communication XIV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1224–1227, September, 1972.     

Investigation of the products of the reaction of epichlorohydrin with aromatic amines

5,6-Dichlorobenzo[f]quinoline is formed by the action of thionyl chloride on 3-hydroxy-5-chloro-1,2,3,4-tetrahydrobenzo[f]quinoline hydrochloride. 7-Chlorobenzo[f]quinoline and 7-chloro-1,2,3,4-tetrahydrobenzo[f]quinoline are obtained in good yields by heating 3-hydroxy-7-chloro-1,2,3,4-tetrahydrobenzo[f]quinoline with orthophosphoric acid, while benzo[f]quinoline is also obtained by heating it with polyphosphoric acid.See [1] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 108–111, January, 1971.     

A spectrophotometric study of the colour reaction between chloranil and aromatic amines

The colour reaction between aromatic amines and chloranil was studied spectrophotometrically. A 1 : 1 adduct formed in solution, with some dissociation. The effects of solvents, acid and alkali were examined. The adducts exhibited intense, and characteristic, broad absorption bands, which could be used for the detection and estimation of an aromatic amine, in the absence of substances of similar light absorption characteristics. A correlation between the basicities of an amine and the ight absorption of the adduct was established.     

The reaction of pentachloropyridine with aromatic amines

The reaction of pentachloropyridine with aromatic amines in dimethylformamide in the presence of sodium carbonate leads to 4-arylaminotetrachloropyridines. The product of the reaction of pentachloropyridine with aniline in pyridine is 4-amino-2,3,5,6-tetrachloropyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 963–965, July, 1970.     

On the reaction of 2-chloroethylisothiocyanate with aromatic amines

The reaction of aromatic amines with 2-chloroethylisothiocyanate 2 to give 2-arylaminothiazolines 1 was investigated. The course of this reaction was found to depend on the electronic nature of the amine and the reaction conditions. With arylamines that are relatively electron-rich, good yields of the thiazolines 1 were obtained. With electron-poor amines, adducts 4 , in which two equivalents of 2 reacted with the amine, accompanied 1. The relative amounts of 2:1 adducts increased as the arylamine became progressively more electron deficient. With 3,4-dichloroaniline, the yields of the 2:1 adducts were promoted by the presence of triethylamine.     

斯德酮与芳香胺的Mannich反应

3－（4－甲基苯甲酰基乙基）斯德酮和3－（3－羟基－3－苯基丙基）斯德酮 可以与芳香胺发生Mannich反应，得到斯德酮与芳香胺的Mannich碱。     

Alginic acid azide and its reaction with aromatic amines

Alginic acid azide is synthesized and its stability in aqueous solutions in dependence on keeping duration and solution pH is studied. Reaction of the azide with aromatic amines is explored.     

Nuclear amination catalyzed by fungal laccases: reaction products of p-hydroquinones and primary aromatic amines

[reaction: see text] Nuclear amination of p-hydroquinones with primary aromatic amines was catalyzed by fungal laccases (EC 1.10.3.2) from Trametes spec. and Myceliophthora thermophila. This is the first report of laccase-catalyzed synthesis of aminoquinones. Incubation of two compounds with laccase in the presence of oxygen resulted in the formation of the corresponding monoaminated or diaminated quinones. No hydroquinonoids were formed. Observed differences in the reaction courses for different p-hydroquinones and aromatic amines with different laccases are discussed.     

A tandem three-phase reaction for preparing secondary amines with minimal side products

[reaction: see text] A new method for the preparation of secondary amines has been reported. Complementary solution-phase and solid-phase synthesis highlight the process. Amines are obtained in good yields free from the usual byproducts of reductive amination. Secondary amines are unreactive, so overalkylation does not occur. The procedure can be used interchangeably for traditional or parallel synthesis settings.     

Structure and reactivity of the condensation products of aromatic amines with aliphatic aldehydes

A number of previously undescribed propylidenearylamine dimers have been synthesized by the interaction of propionaldehyde with a series of para-substituted anilines(R=H, CH₃, OCH₃, F, Cl, Br, I) and with-naphthylamine. The structure of the bis-propylidenearylamines has been established by a study of their IR and UV spectra. It has been shown that all the bis-propylidenearylamines, except for bis(propylidene-p-fluoroaniline), have the structure of 2-ethyl-3-methyl-4-arylamino-1, 2, 3, 4-tetrahydroquinolines. The dipole moments of the bis(propylidene-p-R-anilines) have been determined. Comparison of the values obtained with the calculated values indicates that the most favorable molecular conformation of the bispropylidenearylamines is a tetrahydroquinoline half-chain with quasi-equatorial positions for the 4-NHAr and NH groups and an equatorial 3-CH₃ group. In contrast to the bis-ethylideneanilines, we did not succeed in finding other stable conformers for the bis-propylidene derivatives. It has been established that bis (propylidene-p-fluoroaniline) has the 1, 3-bis (p-fluorophenylamino)-2-ethyl-1-hexene structure.For communication VI, see [1].