First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

• Paweł Borowiecki,
• Daniel Paprocki and
• Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

• dangerous diseases. An irregular and unsanitary lifestyle adversely affects the central nervous system resulting in neuroses and psychiatric disorders. Among the antipsychotic medications phenothiazine derivatives [40][41], and especially promethazine, widely known by its brand name Phenergan®, hold well

• -phenothiazin-10-yl)propan-2-ol (±)-3 was synthesized according to the method described by Clement et al. [59], in which propylene oxide (2) was regioselectively opened by phenothiazine (1) in the presence of n-butyllithium (n-BuLi) at ambient temperature providing desired alcohol (±)-3 in 64–77% yield

• suggests that this particular process is most probably inaccessible through the sodium salt of phenothiazine (1) due to multiple substitution at aromatic ring carbon atoms and some other byproducts of the non-regioselective propylene oxide ring opening. With the hope of eliminating the unwanted side

The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

• Sarah Bay,
• Gamall Makhloufi,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

• ]. This photo-induced electron transfer (PET) [30][31][32][33][34] has been investigated with donors such as porphyrines, polycyclic aromatic hydrocarbons, perylenediimides and (oligo)thiophenes [35][36], tetrathiafulvalenes [37], as well as phenothiazine and its derivatives [22][38][39][40]. The latter

• have become attractive electrophores due to their reversible and tunable oxidation potential. Interestingly quenching of the phenothiazine inherent fluorescence offers a facile evidence for the occurrence of intramolecular PET in phenothiazine-containing Do–Acc dyads [41][42]. As suitable acceptor

• moieties C60 fullerene [43][44][45], and quinones, such as 9,10-anthraquinone as a potential two electron acceptor, have been commonly used in Do–Acc arrangements [46][47][48][49][50][51]. In previous studies phenothiazine–anthraquinone couples have been introduced into peptide scaffolds [52][53][54] and

N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters

• Oliver Goerz and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 902–909, doi:10.3762/bjoc.10.88

• -toluenesulfonic acid, phenothiazine (98%), zinc iodide (98%), and boron trifluoride diethyl etherate (46%) were purchased from Sigma-Aldrich and used as received. Isosorbide (98%) and E-benzaldoxime (97%) were purchased from Alfa Aesar, and isosorbide was recrystallized from acetone/ethyl acetate. All used

• ), crotonic acid (9.04 g, 105 mmol), p-toluenesulfonic acid (0.86 g, 5 mmol), phenothiazine (0.02 g, 0.1 mmol) and 80 mL of toluene. The flask was fitted with a Dean–Stark apparatus and the mixture was heated under reflux for 72 h. The solution was washed with 2 × 40 mL of saturated sodium hydrogen carbonate

• ), 755, 692 (ν, Aryl); ESIMS m/z: 525 [M+]. Synthesis of poly(isosorbide itaconate -co- succinate) 13: A 250 mL round bottom flask was charged with isosorbide (5.85 g, 40 mmol), itaconic acid (2.60 g, 20 mmol), succinic acid (2.36 g, 20 mmol), p-toluenesulfonic acid (0.04 g, 0.2 mmol), phenothiazine

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• with emission maxima at 410–515 nm [75]. A-π-D-π-A molecules 69 featuring a central phenothiazine donor moiety and two peripheral benzimidazole acceptor units were investigated by Ahn et al. [76]. These ambipolar molecules possess energy levels that are well-matched with the Fermi levels of the

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• phenothiazine derivatives 72 starting from primary amines, 2-bromothiophenol and substituted 1-bromo-2-iodobenzenes [40]. Ferrocene ligands, such as dppf, and Pd2dba3 as the palladium source were found to be the most suitable and efficient catalyst systems for the preparation of a series of phenotiazine

• -alkynylindoles through a Pd-catalyzed Sonogashira/double C–N coupling reaction. Synthesis of indoles through a Pd-catalyzed sequential alkenyl amination/C-arylation/N-arylation. Synthesis of N-aryl-2-benzylpyrrolidines through a sequential N-arylation/carboamination reaction. Synthesis of phenothiazine

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• polymer such as P-15 (Table 2) exhibited absorption and fluorescence maxima of 510 and 585 nm, respectively, the fluorescence quantum yield being 66%. Polymer/PCBM bulk heterojunction solar cells exhibited a power conversion efficiency of 0.16%. Cao et al. [53] prepared new fluorene-DPP-phenothiazine

• the electron affinity, and phenothiazine significantly enhanced the hole injection ability. ThiophenylDPP-based copolymers The replacement of the phenyl groups in 3,6-diphenyl-substituted DPP derivatives by thiophenyl groups resulted in 3,6-(2-thiophenyl)-substituted DPP derivatives (thiophenylDPPs

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• towards the synthesis and study of (oligo)phenothiazine-based functional π-systems [40][41][42][43][44][45][46], we have now focused our attention on thiolated phenothiazines and (oligo)phenothiazines as “alligator-clips”. Here, we report the synthesis of phenothiazines and their oligomers bearing

• phenothiazine units are present, e.g., because of a back bending of the thiol-bound molecule to the gold surface in these cases, supported by additional gold-π-interactions with the terminal phenothiazine, which thus would hamper the formation of a SAM with an almost parallel intermolecular orientation. In

• , which can be very useful, for example, for co-adsorption of the moieties with a second, nonconductive molecule, which serves as an insulating matrix. Further studies directed toward such more-complex (oligo)phenothiazine SAMs on gold and functionalized redox manipulable surfaces, the nanoscopic

Synthetic incorporation of Nile Blue into DNA using 2′-deoxyriboside substitutes: Representative comparison of (R)- and (S)-aminopropanediol as an acyclic linker

• Daniel Lachmann,
• Sina Berndl,
• Otto S. Wolfbeis and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2010, 6, No. 13, doi:10.3762/bjoc.6.13

• nucleic acids (TINA) [27][28], and by our group for fluorescent DNA base substitutions by ethidium [29][30], indole [31][32], thiazole orange [33][34], perylene bisimide [35][36] and phenothiazine [37]. This 2′-deoxyriboside substitution provides high chemical stability and conformational flexibility for

• (Scheme 2). In comparison to our earlier synthetic protocols for incorporation of ethidium [29][30], indole [31] and phenothiazine[37] the NH group of the carbamate is less nucleophilic and need not be protected during phosphoramidite synthesis. This facilitates the preparation of DNA building blocks as