Reaction of 4-aryl-2-aminobuta-1,3-diene-1,1,3-tricarbonitriles with CH-nucleophiles: I. Synthesis of 5-aryl-2,4-diamino-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitriles

5-Aryl-2,4-diamino-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitriles were synthesized from 4-aryl-2-aminobuta-1,3-diene-1,1,3-tricarbonitriles and dimedone.     

Three-Component synthesis and characterization of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment

The synthesis of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment through the base-promoted three-component reaction of an aromatic aldehyde, an acetoacetamide and malononitrile dimer in the presence of an oxidant is reported. The HOMO-LUMO energy levels were estimated by cyclic voltammetry and UV-Vis measurements. The influence of aryl and carbomoyl substituents on the optical and electrochemical properties was also investigated.     

Three-component synthesis and optical properties of triarylpyridines containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment

The synthesis of triarylpyridine derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment via the base-promoted reactions of aromatic aldehydes, 2-phenylacetophenone and a malononitrile dimer in the presence of an oxidant is described. The influence of aryl substituents in the 4-position on the optical properties is also reported.     

An improved and facile synthesis of 2-amino-1,1,3-tricyanopropene

A simple method for the dimerization of malononitrile using alkali hydroxides in methanol or ethanol is described. Thereby 2-Amino-1,1,3-tricyanopropene, a keyintermediate for heterocyclic chemistry, is obtained in high yield.

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Eine verbesserte und bequeme Synthese von 2-Amino-1,1,3-tricyan-propen (Kurze Mitteilung)

Zusammenfassung Eine einfache Dimerisierung von Malononitril unter Verwendung von Alkalihydroxid in Methanol und Ethanol wird beschrieben. Dabei entsteht in guter Ausbeute 2-Amino-1,1,3-tricyan-propen, ein wichtiges Ausgangsprodukt zur Synthese von Heterocyclen.

     

Isopropylidenemalononitrile in the synthesis of 2-amino-4,6,6-trimethylcyclohexa-2,4-diene-1,1,3-tricarbonitrile, 6-amino-2-(4-methoxybenzoylmethylsulfanyl)-4,4-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile, and fused 2-aminopyrans according to Michael

Michael reactions of isopropylidenemalononitrile with cyanothioacetamide (in the presence of 4-methoxyphenacyl bromide), cyclohexane-1,3-dione, and 4-hydroxycoumarin, gave 6-amino-2-(4-methoxy-benzoylmethylsulfanyl)-4,4-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile, 2-amino-4,4-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, and 2-amino-4,4-dimethyl-5-oxo-4H,5H-pyrano[3,2-c]-chromene-3-carbonitrile, respectively. In the reaction of isopropylidenemalononitrile with cyanoacetamide, only dimerization product of the former, 2-amino-4,6,6-trimethylcyclohexa-2,4-diene-1,1,3-tricarbonitrile, was isolated. Its structure was proved by X-ray analysis.     

Reaction of 2-amino-4-imino-2-perfluoropentene with ethylenediamine and diethylenetriamine

The transamination of 2-amino-4-imino-2-perfluoropentene with ethylenediamine gives the corresponding 6-fluoro-5,7-bis(trifluoromethyl)-2,3-dihydro-1H-1,4-diazepine. The transamination of 2-amino-4-imino-2-perfluoropentene by diethylenetriamine is accompanied by intramolecular nucleophilic substitution of the α-fluorine atom to form 1,9-bis(trifluoromethyl)-3,4,6,7-tetrahydro-2H-pyrazino[1,2-a]pyrazine whose structure was established by an X-ray structural investigation. Several salts of this bicyclic compound and its complex with BF₃ have been described. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1773–1776, October, 1993.     

Synthesis of substituted 2-amino-4H-1,3-oxazines

4,4,6-Trimethyl-2-methylarylamino-4H-1,3-oxazines were synthesized by intramolecular cyclization of N-oxoalkyl-S-methylisothioureas.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 764–767, June, 1974.     

Reaction of 4-Methylene-1,3-dioxolan-2-ones with Hydrazines

The structure of the products of the reaction of 4-methylene-1,3-dioxolan-2-ones with hydrazines is a function of the structure of the starting hydrazine. 1,3,4-Oxadiazin-2-one derivatives are obtained from hydrazine hydrate. 3-Arylaminooxazolidin-2-ones are obtained from monoarylhydrazines, while mixtures of these derivatives are obtained from aliphatic monoalkylhydrazines.     

Oxidation of 4-amino-1,3-dimethylpyrazole

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 998–999, July, 1989.     

Reaction of <Emphasis Type="Italic">N</Emphasis>-aryl-3-oxobutanethioamides with 2-amino-1,3-thiazole and 2-amino-1,3-benzothiazole

N-Aryl-3-oxobutanethioamides react with 2-amino-1,3-thiazole (2-amino-1,3-benzothiazole) in acetic acid to give mixtures of 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-thione (2-methyl-4H-pyrimido-[2,1-b][1,3]benzothiazole-4-thione) and 5-arylimino-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidines (4-arylimino-2-methyl-4H-pyrimido[2,1-b][1,3]benzothiazoles), whose ratio depends on the nature of the aryl substituent in the initial butanethioamide.     

Synthesis of substituted 2-amino-5,6-dihydro-4h-1,3-oxazines and 2-iminotetrahydro-1,3-oxazines

3,4,4,6-Tetramethyl-2-aryliminotetrahydro-1,3-oxazines were synthesized by intramolecular cyclization of N-aryl-N′-methyl-N′-(2-methyl-4-hydroxy-2-pentyl)-S-methylisothioureas. 4,4,6-Trimethyl-2-(N-methyl-N-arylamino)-5,6-dihydro-4H-1,3-oxazines were obtained by methylation of 4,4,6-trimethyl-2-arylamino-5,6-dihydro-4H-1,3-oxazines.     

5-Acyl-4-amino-2-phenyl-1,3-oxazin-6-ones

Intramolecular cyclization of acyl(ethoxycarbonyl)keteneN-benzoylaminals in boiling Ph₂O gives 5-acyl-4-amino-2-phenyl-1,3-oxazin-6-ones.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1322–1323, July, 1995.This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-08964).     

Synthesis of substituted 2-amino-5,6-dihydro-4H-1,3-thiazines and 2-iminotetrahydro-1,3-thiazines

N-Aryl-N′-(2-methyl-4-hydroxy-2-pentyl)thioureas are cyclized in acidic media to 4,4,6-trimethyl-2-arylimino-5,6-dihydro-4H-1,3-thiazines, the methylation of which with methyl iodide gives 4,4,6-trimethyl-2-methylarylamino-5,6-dihydro-4H-1,3-thiazines. 3,4,4,6-Tetramethyl-2-aryliminotetrahydro-1,3-thiazines were synthesized by cyclization of Naryl-N′-methyl-N′-(2-methyl-4-hydroxy-2-pentyl)thioureas.     

Reaction of 6-amino-1,3-dimethyluracil with hexafluoroacetone and ethyl trifluoropyruvate benzoylimines

Heating of 6-amino-1,3-dimethyluracil with hexafluoroacetone and ethyl trifluoropyruvate benzoylimines in DMF in the presence of Et₃N results in 1,3-dimethyl-7-phenyl-5,5-bis(trifluoromethyl)-1,2,3,4,5,8-hexahydropyrimido[4,5-d]pyrimidine-2,4-dione and 5-benzoylamido-1,3-dimethyl-5-trifluoromethyl-1,2,3,4,5,6-hexahydropyrrolo[2,3-d]pyrimidine-2,4,6-trione, respectively.