Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion

Abstract

Tetrapyrazinoporphyrazine with peripheral menthol-thiophenyl substituents was synthesized using Linstead conditions and purified by flash column chromatography. The optimized synthetic and purification procedures allowed us to obtain a new macrocycle with 36% yield. Tetrapyrazinoporphyrazine derivative was characterized by UV–Vis and NMR spectroscopy, as well as MS spectrometry. Complex NMR studies using 1D and 2D NMR techniques allowed the analysis of the bulky menthol-thiophenyl substituted periphery of the new macrocycle. Further, photochemical stability and singlet oxygen quantum yield were determined by indirect method with diphenylisobenzofuran. The new tetrapyrazinoporphyrazine revealed low generation of singlet oxygen with a quantum yield of singlet oxygen formation at 2.3% in dimethylformamide. In turn, the macrocycle under irradiation with visible light presented very high stability with quantum yield for photostability of 9.59 × 10−6 in dimethylformamide, which figures significantly exceed the border for its classification as a stable porphyrinoid (10−4–10−5).

Special Issue on Synthesis of Novel Heterocyclic Compounds and Evaluation of Their Antimicrobial Activity

“…In the next paper, Potapov et al [3] report the synthesis of a group of new and highly soluble compounds as a product of annulation reactions of 8-quinolinesulfenyl halides with natural origin alkenes. Using this method, a series of [1,4] thiazino [2,3,4-ij]quinolin-4-ium was obtained with almost quantitative yields. Reactions with styrene derivatives and other terminal alkenes proceeded in a regioselective manner but with the opposite regiochemistry.…”

“…The reaction products of 8-quinolinesulfenyl halides with 1H-indene, eugenol, methyl eugenol and 1-heptene proved to be particularly effective. Lijewski et al [4] described the synthesis of complex compounds with condensed heterocyclic rings, which contained a porphyrazine system fused with pyrazine rings, which were substituted with a menthol-thiophenyl group in the peripheral zone. Moreover, inside the porphyrazine ring, there was a magnesium ion (Mg(II)) centrally bonded through coordinated bonds as a complex connection.…”