2-Amino-1,2,3-triazole derivatives

The syntheses and structure of 2-triarylphosphoranimine-1,2,3-triazole derivatives from vicinal diazides have been investigated. Compounds derived from dichloronapththoquinone, 2,3-dichloro-5,6-dimethylbenzoquinone, and 2,3,5,6-tetrachlorobenzoquinone are included. X-ray structures, NMR, IR, UV, and cyclic voltammetry data are reported. Compound 2 crystallizes in space group with a = 12.31(1), b = 12.469(3), c = 10.088(3) Å, = 97.19(3), = 103.79(6), = 101.84(4)°, and D _calc = 1.466 g/cm for Z = 2. Compound 4 crystallizes in space group P2₁/c with a = 9.044(2), b = 10.882(2), c = 19.110(4) Å, = 99.06(2)°, and D _calc = 1.324 g/cm for Z = 2. Compound 6 crystallizes in space group P2₁/a with a = 8.85(1), b = 14.841(8), c = 11.372(8) Å, = 107.19(3)°, and D _calc = 1.397 g/cm for Z = 4. Compound 11 crystallizes in space group P2₁/n with a = 8.823(3), b = 16.501(6), c = 16.221(3) Å, = 103.58(2)°, and D _calc = 1.309 g/cm for Z = 4. Compound 12 crystallizes in space group with a = 11.606(8), b = 11.671(5), c = 10.734(3) Å, = 101.62(3), = 93.70(4), = 64.33(4)°, and D _calc = 1.438 g/cm for Z = 2. Compound 13 crystallizes in space group C2/c with a = 13.337(7), b = 9.217(6), c = 24.78(1) Å, = 102.85(5)°, and D _calc = 1.478 g/cm for Z = 8.     

The Further Cross-Linking of Polydiallylamines with Dihalo Compounds

Highly swollen ion-exchange resins result from the polymerization of diallylamine in the presence of 2 mol% of a bis-diallyl-amino compound as the cross-linking reagent. It is shown that post cross-linking with a dihalo compound is an acceptable method for decreasing the swelling propensity of the resins. The secondary amino groups are then converted to tertiary types, although there is some formation of quaternary ammonium groups which is detrimental in ion-exchange resins which are to be regenerated thermally. The aromatic compound α,α-dichloro-p-xylene is more suitable than the less rapidly reacting aliphatic compound Br(CH₂)₄Br and the even slower reacting reagent Cl(CH₂)₄Cl. However, satisfactory products are obtained with the use of Br(CH₂)₆Br. The additional cross-linking of the poly-diallylamine results in a lowering of the basicity level by one to two orders of magnitude, with the electron-withdrawing aromatic product exhibiting the greatest effect. Better pH buffering properties are usually obtained when the product is subsequently treated with hot alkali, which transforms any quaternary ammonium groups present to tertiary amino types.     

Pterocaryquinone, a Novel Naphthoquinone Derivative from Pterocarya tonkinesis

Pterocaryquinone,a novel 1,4-naphthoquinone derivative,was isolated from Pterocarya tonkinesis and itsstructure was elucidated by spectroscopic methods.Pterocaryquinone is a new dimeric 1,4-naphthoquinone deriva-tive having a pentacyclic skeleton with two five-membered carbon rings,which provided a novel structural skeletonfor 1,4-naphthoquinone derivatives and showed apoptosis-inducing activity toward mouse cancer tsFT210 cells.     

A new naphthoquinoneimine derivative from the marine algal-derived endophytic fungus Aspergillus niger EN-13

Cultivation of an endophytic fungus Aspergillus niger EN-13 that was isolated from the inner tissue of the marine brown alga Colpomenia sinuosa resulted in the characterization of a new naphthoquinoneimine derivative,namely,5,7-dihydroxy-2-[1-(4- methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone.The structure of the new compound was established on the basis of various NMR spectroscopic analyses including 2D NMR techniques,EI-MS,and HR-ESI-MS.This compound displayed moderate antifungal activity.     

Reaction of 2,3‐Dichloro‐1,4‐Naphthoquinone with 1‐Phenylbiguanide and 2‐Guanidinebenzimidazole

When 2,3‐dichloro‐1,4‐naphthoquinone (DCHNQ) ( 1 ) is allowed to react with 1‐phenylbiguanide (PBG) ( 2 ), 4‐chloro‐2,5‐dihydro‐2,5‐dioxonaphtho[1,2‐d]imidazole‐3‐carboxylic acid phenyl amide ( 4 ), 6‐chloro‐8‐phenylamino‐9H‐7,9,11‐triaza‐cyclohepta[a]naphthalene‐5,10‐dione ( 5 ) and 4‐dimethyl‐amino‐5,10‐dioxo‐2‐phenylimino‐5,10‐dihydro‐2H‐benzo[g]quinazoline‐1‐carboxylic acid amide ( 6 ) were obtained. While on reacting 1 with 2‐guanidinebenzimidazole (GBI) ( 3 ) the products are 3‐(1H‐benzoimidazol‐2‐yl)‐4‐chloro‐3H‐naphtho[1,2‐d]imidazole‐2,5‐dione ( 7 ) and 3‐[3‐(1H‐benzoimidazol‐2‐yl)‐ureido]‐1,4‐dioxo‐1,4‐dihydronaphthalene‐2‐carboxylic acid dimethylamide ( 8 ).     

An efficient and facile synthesis of substituted cinnoline and benzo[h]cinnoline derivatives

New substituted 3-amino-5,7,8-trihalo-6-hydroxycinnoline-4-carbonitriles 7 and 8 and the 3-amino-5-chloro-6-hydroxy-benzo[h]cinnoline-4-carbonitrile 9 were synthesized in two-steps starting from tetrahalo-1,4-benzoquinones or dichloro-1,4-naphthoquinones, malononitrile and hydrazine.     

Synthesis of Nitro‐Octaaza Derivatives of Reduced Anthracene

Nitro compounds of octaaza derivatives of reduced anthracene were synthesized for the first time by reaction of 2,3,4a,6,7,8a,9,10‐octaaza‐4,8‐dioxo‐3,4,4a,7,8,8a,9,9a,10,10a‐decahydroanthracene with nitric acid, mixed nitric acid/sulfuric acid, and nitric acid/acetic anhydride at between –20 and –30 °C. In addition, 1,2,4,5‐tetrazine azido derivatives were obtained by hydrolytic decomposition of the starting compound by nitrous acid. All the resultant compounds exhibit high thermal stability.     

SYNTHESIS OF 5-DODECANOYLAMINE-8-HYDROXY-1,4-NAPHTHOQUINONE AND STUDY OF SOME OF ITS BIVALENT METAL CHELATES

Abstract

Two new naphthoquinone derivatives, 5-dodecanoylamine-8-hydroxy-l,4-naphthoquinone (1) and 5-dodecanoylamine-8-acetoxy-l,4-naphthoquinone (2), have been prepared and characterized. Their chelating ability with Ni(II) and Co(II) have been studied. Compound (1) coordinates to the divalent metal ions as a monoanionic bidentate ligand. The complexes were found to contain two ligands and two molecules of coordinated water. The structure and bonding of the chelates are discussed based on the spectroscopic data.