Reaction of alkyl- and arylamines with 2-(hydroxyimino)-3-oxobutanal

The condensation of 2-(hydroxyimino)-3-oxobutanal with primary aliphatic amines, cyclohexanamine, and amines containing an adamantane fragment afforded 4-(alkylamino)- and 4-(cyclohexylamino)-3- nitrosobut-3-en-2-ones. Analogous reaction with substituted anilines RC₆H₄NH₂ (R = H, 4-Me, 4-OMe, 4-NH₂, 4-Br, 4-I, 3-NO₂) led to the formation of 4-aryl-3-hydroxyiminobutan-2-ones.     

Synthesis of 2,4,5-substituted oxazoles from 2-hydroxyaromatic aldehydes

Russian Journal of Organic Chemistry -     

Cyclocondensation of Nitromalonaldehyde Sodium Salt with Substituted 1-Amino-3-butanones

Cyclocondensation of nitromalonaldehyde sodium salt with substituted 1-amino-3-butanones afforded 2-dimethyl-, diethylaminomethyl-4-nitrophenols and 2-piperidylo-, morpholylomethyl-4-nitrophenols.     

Synthesis of nitroso- and amino derivatives of <Emphasis Type="Italic">N</Emphasis>-arylaminoalkyladamantanes

By amination of 4-nitrosophenol and 1-nitroso-2-naphthol the corresponding N-arylaminoalkyladamantanes were obtained whose reduction provided 1,4-phenylenediamines and 1,2-naphthylenediamines.     

Synthesis and reduction of <Emphasis Type="Italic">N</Emphasis>-substituted 5-nitrosoquinolin-8-amines

N-Substituted 5-nitrosoquinolin-8-amines were synthesized for the first time by amination of 5-nitrosoquinolin-8-ol with primary aliphatic amines. The amination of 5-nitrosoquinolin-8-ol with hexamethylenediamine afforded N¹,N⁶-bis(5-nitrosoquinolin-8-yl)hexane-1,6-diamine. The resulting nitrosoquinolinamines were reduced with hydrazine hydrate over Pd/C to N⁸-alkylquinoline-5,8-diamines and N¹,N⁶-bis-(5-aminoquinolin-8-yl)hexane-1,6-diamine.     

4,4-Dimethoxybutan-2-one in the synthesis of 4-nitrosopyrazoles

Russian Journal of Organic Chemistry -     

Synthesis of 2-aryl-3H-naphtho[1,2-d]imidazoles containing an adamantane fragment

N ²-[1-(1-Adamantyl)alkyl]naphthalene-1,2-diamines reacted with benzoyl chlorides in chloroform in the presence of triethylamine to give N-{2-[1-(1-adamantyl)alkylamino]naphthalen-1-yl}benzamides which underwent intramolecular cyclization to 2-aryl-3H-naphtho[1,2-d]imidazoles on heating in toluene in the presence of p-toluenesulfonic acid. 3-[(1-Adamantyl)methyl]-2-(3-nitrophenyl)-3H-naphtho[1,2-d]imidazole was synthesized from N ²-[(1-adamantyl)methyl]naphthalene-1,2-diamine and 3-nitrobenzaldehyde.     

Novel Derivatives of Adamantyl-substituted Quinolin-6-amines and Synthesis of Imidazo[4,5-f]quinolines Therefrom

Russian Journal of Organic Chemistry - N-(Adamantan-1-yl)alkyl-substituted 5-nitrosoquinolin-6-amines were synthesized for the first time by the amination of 5-nitrosoquinolin-6-ol with primary...