Synthesis and structure of new 3,7,10-substituted-phenothiazine derivatives

Abstract

Abstract:The synthesis of new 3,7-dibromophenothiazine derivatives bearing bromoalkyl, mercaptoalkyl and alkylthioacetate groups on the N atom at position 10 is reported. The Suzuki coupling reaction of one of these derivatives via the bromine atoms at positions 3 and 7 with bromothiophene derivatives is also discussed. © Versita Warsaw and Springer-Verlag Berlin Heidelberg.

Rapid Access to New Angular Phenothiazine and Phenoxazine Dyes

“…Burgess noted in his review of benzophenoxazine‐based dyes for labeling biomolecules that most of the synthetic protocols involved elevated temperature and were based on procedure that are now over a century old and no contemporary synthetic methods were employed. However, in the recent time, a considerable variety of phenothiazine derivatives had been synthesized from iodo‐substituted and/or bromo‐substituted phenothiazine precursor via metal catalyzed cross‐coupling reactions . Grosu et al reported multistep synthesis of 3,7,10‐substituted phenothiazine derivatives in which one of the steps involved Pd‐catalyzed Suzuki–Miyaura cross‐coupling of bromophenothiazines.…”

“…However, in the recent time, a considerable variety of phenothiazine derivatives had been synthesized from iodo‐substituted and/or bromo‐substituted phenothiazine precursor via metal catalyzed cross‐coupling reactions . Grosu et al reported multistep synthesis of 3,7,10‐substituted phenothiazine derivatives in which one of the steps involved Pd‐catalyzed Suzuki–Miyaura cross‐coupling of bromophenothiazines. Kramer employed the Suzuki–Miyaura cross‐coupling of bromophenothiazine in the synthesis of (hetero) aryl bridged and directly linked active phenothiazinyl dyads and triads.…”

Macrocycles embedding phenothiazine or similar nitrogen and/or sulphur containing heterocycles

“…The phenothiazine has a flattened ''butterfly'' structure (similar with the structure of 9,10-dihydroanthracene, [25] ), while the radical-cation formed by its oxidation is planar [26,27]. Due to these interesting properties phenothiazine derivatives are widely used for the obtaining of new materials such as: electroactive polymers [28][29][30], dyads and triads [31][32][33][34], cruciform fluorophores [35], molecular wires [36] or ligands for surface modifications [37][38][39]. Innovative redox-active materials were obtained with compounds showing two or more (up to seven) phenothiazines directly connected to each other [40][41][42][43] or via ethynyl or aryl units [44][45][46][47].…”

Synthesis, characterization and photochemical properties of metallo porphyrazines substituted with alkyl linked carbazole, benzoazepine and phenothiazine moieties

“…10-(6-Bromohexyl)-10H-phenothiazine (3) used as the first step starting compound was prepared in considerable yield using a known synthetic method [17] and spectroscopic data such as 1 H, 13 C-NMR and FT-IR also given on the contrary to the mentioned literature. In the 1 H and 13 C-NMR spectra of this compound, the characteristic resonances for the aromatic or aliphatic protons and carbons were very similar to those of the same compounds [21].…”

“…Unless otherwise stated, all reactions were carried out under argon atmosphere in a vacuum line or using Schleck techniques. cis-1,2-Dicyano-1,2-ethylenedithiolate (4) [15], 9-(6-bromo-hexyl)-9H-carbazole (9) [16] and 10-(6-bro mo hexyl)-10H-phenothiazine (3) [17] were prepared according to the literature procedures.…”