Amination of 1,3-dihalo-2-nitrosobenzenes

1,3-Dichloro-2-nitrosobenzene and 1,3-dibromo-5-fluoro-2-nitrosobenzene reacted with amines to give previously unknown nitrosobenzene derivatives containing alkylamino groups in positions 3 and 5.     

Reaction of 5-chloroanthra[1,9-cd]-6-isoxazolone with oxygen-containing nucleophiles

Facile nucleophilic substitution of the chloride ion to give 5-alkoxy- or 5-aryloxy-anthra[1,9-cd]-6-isoxazolones occurs in the reaction of 5-chloroanthra[1,9-cd]-6-isoxazolone with alcohols and phenols. The possibility of conversion of the synthesized isoxazolones to 1-amino-4-alkoxyanthraquinones is demonstrated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1329–1331, October, 1983.     

Synthesis of 6H-Naphtho[1,2,3-cd]indol-6-ones

S,S-Dimethyl-and S-methyl-S-phenyl-N-(9,10-anthraquinon-1-yl)sulfoximides are converted into 6H-naphtho[1,2,3-cd]indol-6-ones on heating in polar aprotic solvents.     

Unusual reaction between 6H-6-oxo-5-haloanthra[1,9-cd]-isoxazoles and quinoline

The reaction of 6H-6-oxo-5-haloanthra[1,9-cd]isoxazoles with quinolines leads to unexpected fragmentation of the quaternized quinoline ring to give xylidine or o-toluidine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1682–1686, December, 1986.     

Reaction of 5-haloanthra[1,9-cd]-6-isoxazolones with aziridine

The reaction of 5-haloanthra[1,9-cd]-6-isoxazolones with aziridine gave 5-aziri-dinoanthra[1,9-cd]-6-isoxazolones. The latter, upon reaction with acids, undergo cleavage of the aziridine ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 885–888, July, 1984.     

Synthesis of 4(6)-aryloxy- and 4-arylthio-2,1,3-benzoxadiazoles

Reactions of 4,6-dibromo-2,1,3-benzoxadiazole with phenols or arenelthiols lead to 4-aryloxy-6-bromo-2,1,3-benzoxadiazoles or 4-arylthio-6-bromo-2,1,3-benzoxadiazoles, respectively. Isomeric 6-aryloxy-4-bromo-2,1,3-benzoxadiazoles were synthesized by replacement of the fluorine atom in 2,6-dibromo-4-fluoro-1-nitrosobenzene with phenols and treatment of the resulting 4-aryloxy-2,6-dibromo-1-nitrosobenzene with sodium azide.     

Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones

Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones.     

Reactions of 1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone with ninhydrin

Russian Chemical Bulletin - 1,4-Naphthoquinone and 5-hydroxy-1,4-naphthoquinone react with ninhydrin to give 2-(2-hydroxy-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)naphthalene-1,4-dione and 8-hydroxy-...