Synthesis of 4-(4-hydrazinylphenoxy)phthalonitrile and phthalonitriles on its basis containing N-heterocycles

Abstract

The synthesis of the novel 4-(4-hydrazinylphenoxy)

Synthesis and Isolation of 2,9,17,23-Tetrakis[(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]phthalocyanine and Its Magnesium(II) and Zinc(II) Complexes

“…The magnesium phthalocyanine 3 and zinc phthalocyanine 4 were prepared by cyclotetramerization of known phthalonitrile 1 [49] in the presence of anhydrous acetate salts of metals using DBU as the catalyst in 1-pentanol under reflux for 10 h as described for the last in work. [48] Metal-free phthalocyanine 2 was synthesized by two different methods.…”

“…4-(4-(3,5-Dimethyl-1H-pyrazol-1-yl)phenoxy)phthalonitrile (1) was synthesized using known procedure. [49] The individuality of the products was monitored by thin layer chromatography (TLC) on Silufol UV-254 plates and compounds were visualized by exposure to UV light. All synthesized phthalocyanines 2-4 were purified by column chromatography at first column on Al 2 O 3 (Sigma-Aldrich) using chloroform as an eluent, second column on Al 2 2 (0.068 g, 0.477 mmol) was added into a singlenecked flask and heated to the boiling point.…”

“…[47] Moreover, it was shown that the photophysical, photochemical and photobiological properties of regioisomers were different and C S regioisomer possessed a more effective action on cell death. [45] Recently [48] we have published a paper dealing with the synthesis and isolation of C S regioisomer zinc 2,9,17,23-tetrakis[(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]-phthalocyanine by cyclotetramerization of 4-(4-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]phthalonitrile [49] and zinc acetate with DBU in 1-pentanol. This paper is devoted to the two methods of synthesis of 2,9,17,23-tetrakis[(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]-phthalocyanine 2, its magnesium complex 3 from phthalonitrile 1 and zinc complex 4 from phthalocyanine ligand 2 and isolation of practically pure C S regioisomers.…”

Corrosion Resistance of Aluminum against Acid Activation: Impact of Benzothiazole-Substituted Gallium Phthalocyanine

“…Vibrational signals characteristic of phthalonitriles and ascribed to C-N moieties [47] appeared in the spectrum of BTThio at 2231 cm −1 (before corrosion) as Figure 8 shows and this peak disappeared after corrosion, suggesting the involvement of the C–N groups as adsorption sites for BTThio onto the metal surface. Vibrational signals at 1534 cm −1 (–CN), 1424 cm −1 (–CH 2 ), 1279 cm −1 (C–H), 1077 cm −1 (C=C and –CN) and 910–720 cm −1 (aromatic C=C and C–H) have been ascribed earlier [7,48,49,50].…”

Synthesis of zinc phthalocyanine containing 4-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy groups

“…Complex 2 was synthesized by tetramerization of phthalonitrile 1 [6] in pentan-1-ol in the presence of anhydrous zinc acetate and DBU as catalyst. The IR spectrum of 2 contained absorption bands due to stretching vibrations of the isoindole fragments and bending vibrations of the phthalocyanine macrocycle at 1334 and 746 cm -1 , respectively, as well as due to stretching vibrations of aromatic and aliphatic C-H bonds and ether fragments C arom -O-C arom at 3067, 2920, 2846, and 1231 cm -1 , respectively.…”