Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

Abstract

Two unique structures were isolated from the phosphorylation reaction of 10H-phenothiazine. The 5,5-dimethyl-2-(10H-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide (2a) illustrates the product of N-phosphorylation of phenothiazine. Moreover, a potential product of 2a instability, a thiophosphoric acid 2b, was successfully isolated and structurally characterized. Molecule 2a, similarly to sulfoxide derivative 3, possesses interesting phosphorescence properties due to the presence of d-pπ bonds. The X-ray, NMR, and DFT computational studies indicate that compound 2a exhibits an anomeric effect. Additionally, the syntheses of selected symmetrical and unsymmetrical pyridine-embedded phenazines were elaborated. To compare the influence of phosphorus and sulfur atoms on the structural characteristics of 10H-phenothiazine derivatives, the high-quality crystals of (4a,12a-dihydro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxalin-12-yl)(phenyl)methanone (1) and selected phenazines 5,12-diisopropyl-3,10-dimethyldipyrido[3,2-a:3′,2′-h]phenazine (5) and 5-isopropyl-N,N,3-trimethylpyrido[3,2-a]phenazin-10-amine (6a) were obtained. The structures of molecules 1, 2a, 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (2b), 3,7-dinitro-10H-phenothiazine 5-oxide (3), 5 and 6a were determined by single-crystal X-ray diffraction measurements.

Phenothiazine-Based Cu(II)-Selective Fluorescent Sensor: GHK-Cu Sensing Applications

“…Found: C, 69.67; H, 4.60; N, 5.82; S, 13.30. The compound exhibited identical 1H and 13C {1H} NMR data to the previous report …”

“…13 C { 1 H} NMR (100 MHz, CDCl 3 ) δ: 189.9, 150.9, 144.0, 131. 42 4.2.3. Synthesis of 7-Bromo-10-methyl-10H-phenothiazine-3carbaldehyde (1d).…”

New Isomeric Dipyridothiazine Dimers — Synthesis, Structural Characterization and Cytotoxicity Screening

“…There are completely synthetic compounds that have no precursor of their own in the animate natural world [1,2]. Although phenothiazine was discovered more than 140 years ago by German researcher August Bernthsen to this day the molecule is still very popular in the world of medical, pharmaceutical as well as chemical research [3][4][5].…”