Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• intramolecular electronic coupling of (oligo)phenothiazines [45][64] and the low torsional displacement from a coplanar arrangement of both redox moieties of the dumbbells might represent conjugatively linked nanometer-scaled novel multistep redox active oligomers. As part of our concept to develop novel

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• multistep synthesis of cannabinergic lactones from dimethylheptylresorcinol. Two regioisomeric cannabinergic lactones were obtained, one of which possessed pronounced affinity towards the CB1 receptor and lower affinities for mCB2 and hCB2 receptors [228]. Oxidation with H2O2–acid systems: With in situ

• [280][281][282] as the catalyst. The obtained asymmetric oxidation products can be used in the multistep synthesis of new biologically active compounds. Possible mechanisms for the asymmetric oxidation of 3-substituted cyclobutanone 96a with H2O2 catalyzed by chiral phosphoric acid are presented in

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• multistep process (Scheme 9). After elongation by the iterative type I fatty acid synthase MmpB, redox transformations and a dehydration on the MacpE-bound substrate 58 finally lead to pseudomonic acid A (61) with a 3,4-dihydroxy-2,5-disubstituted pyran ring. The reason for the elaborate oxidation–reduction

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• as its complicated multistep synthesis, low hole mobility in its pristine form, and expensive fabrication costs of the PSCs due to the sublimable small molecule. Accordingly, solution-processable hole-transporting polymers with simple structures have also been pursued as HTMs in the PSCs. Common p

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

• compound 10 no full conversion to the desired star-shaped compound was observed under the applied reaction conditions (SiCl4, EtOH) [60][61], very likely due to the insolubility of the intermediates involved in this multistep process. The chloro-substituted 2,2´-bipyridine derivative 5g – available due to

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• simple approach is tedious and time consuming; however the proper choice of conditions allows obtaining satisfactory yields of the unsymmetrically substituted diaryls in most cases. The first step of such multistep processes requires fine tuning of the reaction conditions to maximize the yields of the

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• single modern computing node) allows for a screening of tens of candidates per day in production mode. Our multistep strategy relies on the reproduction of 1) experimentally known ribosome–drug complex geometries, 2) experimentally known ribosome–drug complex affinities 3) the known enantioselectivity of

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• of Victoria, I knew very little about Japan and almost-nothing about the Japanese Language. (Karate had taught me to count from 1 to 10). Having just finished a project with a lot of multistep synthesis, I was immediately drawn to projects as part of the boronic acid research group. The boronic acid

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

• Brett N. Hemric and
• Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

• class of molecules is highly valued. Toward this end, intermolecular olefin oxyamination allows for direct and modular installation of both oxygen and amino groups to readily available olefins in a single step, representing a powerful and appealing approach over multistep sequences [7][8][9]. Sharpless

Effective immobilisation of a metathesis catalyst bearing an ammonium-tagged NHC ligand on various solid supports

• Krzysztof Skowerski,
• Jacek Białecki,
• Stefan J. Czarnocki,
• Karolina Żukowska and
• Karol Grela

Beilstein J. Org. Chem. 2016, 12, 5–15, doi:10.3762/bjoc.12.2

• designed to facilitate straightforward removal of the metal-containing species after the reaction is completed. Although this idea is simple, the preparation of such sophisticated nanoparticle-supported catalysts is often a complicated multistep procedure. Definitely, the simplest and quickest

A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines

• Tarn C. Johnson and
• Stephen P. Marsden

Beilstein J. Org. Chem. 2016, 12, 1–4, doi:10.3762/bjoc.12.1

• ring, exemplified by approaches to the core of the cyclothiazomycins [9][10]. Regardless of the method employed, these are multistep protocols, frequently employing moisture-sensitive organometallic agents or reducing agents. In this paper, we report a new one-pot, two-component synthesis of 2-(1

Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• usually performed by joining the two phosphate moieties at the end of the multistep synthesis [24][25][26][27][28][29]. Similarly, the preparation of the new cpIMP derivative 4 could be performed by the cyclization of a monophosphate precursor via phosphodiester bond formation. For this purpose we

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

• Tsuyuka Sugiishi,
• Hideki Amii,
• Kohsuke Aikawa and
• Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

• materials or require expensive reagents and a multistep synthesis. The [18F]trifluoromethylation performed with commercially available reagents by using [18F]fluoride demands no complex such as [18F]CF2Cu, and thus the method should contribute to efficient PET imaging [42] (Scheme 8). Synthesis of

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• receptors and antileishmanial activity [15][16][17]. Up to date no general non-catalytic approach to N,N’-diarylpolyamines has yet been described. Synthetic procedures are multistep [17][18] though sometimes they can be performed as one-pot syntheses [19]. Several catalytic approaches have been described in

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• of 3,5-dimethylcycloheptatrienecarboxylic acid to 3,5-dimethoxycycloheptatriene, bromination of the latter in chloroform to give β-methoxytropone and its subsequent demethylation [13]. The more general approach to β-tropolone was based on the multistep transformation of 3,4,5-trimethoxybenzoic acid

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes

• Artem A. Zemtsov,
• Alexander D. Volodin,
• Vitalij V. Levin,
• Marina I. Struchkova and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2015, 11, 2145–2149, doi:10.3762/bjoc.11.231

• ][11]. Alternatively, functional group manipulations starting from available CF2-containing building blocks can be considered, but multistep sequences render this approach laborious [12][13][14]. Difluoro-substituted cyclopropanes and cyclopropenes constitute a specific class of compounds accessible by

Supramolecular chemistry: from aromatic foldamers to solution-phase supramolecular organic frameworks

• Zhan-Ting Li

Beilstein J. Org. Chem. 2015, 11, 2057–2071, doi:10.3762/bjoc.11.222

• course among the others. In particular, I enjoyed one course called “Organic Synthesis Skills” taught by Professor Zhixin Huang, which introduced multistep synthesis. I must say that since 1987 I have benefited greatly from this course as a graduate student at the Shanghai Institute of Organic Chemistry

• institution for organic chemistry in China. Studying at SIOC: N···I interaction I joined SIOC in late August of 1987. For many years, graduate students in the first year studied physical organic chemistry, organic synthesis, and organic analytical chemistry. Impressively, all students performed 6–8 multistep

Synthesis of constrained analogues of tryptophan

• Elisabetta Rossi,
• Valentina Pirovano,
• Marco Negrato,
• Giorgio Abbiati and
• Monica Dell’Acqua

Beilstein J. Org. Chem. 2015, 11, 1997–2006, doi:10.3762/bjoc.11.216

• ][12][13]. First of all, modulation of substituents around the terahydrocarbazole nucleus is achievable without the formation of regioisomeric derivatives. Moreover, there is no need of multistep sequences for the synthesis of starting materials. Methyl 2-acetamidoacrylate is a commercially available

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

• Meriem K. Abderrezak,
• Kristýna Šichová,
• Nancy Dominguez-Boblett,
• Antoine Dupé,
• Zahia Kabouche,
• Christian Bruneau and
• Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

• straightforward way for the synthesis of difunctional compounds suitable for polymer syntheses [12][13], fine chemicals [14][15][16][17], or as key synthetic tool in multistep syntheses of complex molecules [18][19][20][21]. Cross metathesis with functional olefins is of great interest as it offers the

The simple production of nonsymmetric quaterpyridines through Kröhnke pyridine synthesis

• Isabelle Sasaki,
• Jean-Claude Daran and
• Gérard Commenges

Beilstein J. Org. Chem. 2015, 11, 1781–1785, doi:10.3762/bjoc.11.193

• nonsymmetric quaterpyridines; Constable et al. proposed a multistep synthesis of 4’-(alkylthio)quaterpyridines [23] to avoid the Stille palladium-catalyzed coupling, whereas Fallahpour obtained the 4’-nitroquaterpyridine by employing the Stille coupling method [24]. Sauer et al. extended the use of triazine

• ”’-quaterpyridines was described that required a multistep synthesis producing elaborate intermediates [24][27]. This short survey of the different ways to produce quaterpyridines (and in particular, nonsymmetric quaterpyridines) shows that a new simple synthesis can be quite relevant. The synthetic approach adopted

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• , these compounds were available only through multistep sequences, most notably one involving as the final step an SNAr reaction with the amine and having the serious limitation of requiring the presence of an additional strong electron-withdrawing group at C-5 [42][43][44]. Our protocol requires only two

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• + owing to the intermolecular mix-valence interaction between the TTF•+ and TTF moieties, and the further oxidation forms 313+ [68]. In summary, the oxidation of 28–31 showed multistep processes owing to intra- and/or intermolecular interactions between TTF units. In the case of [18]annulene 31, the first

Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition

• Zachary L. Palchak,
• Paula T. Nguyen and
• Catharine H. Larsen

Beilstein J. Org. Chem. 2015, 11, 1425–1433, doi:10.3762/bjoc.11.154

• Zachary L. Palchak Paula T. Nguyen Catharine H. Larsen Department of Chemistry, University of California, Riverside, CA 92521, USA 10.3762/bjoc.11.154 Abstract Propargylamines are popular substrates for triazole formation, but tetrasubstituted variants have required multistep syntheses involving

Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

• Iris Binyamin,
• Shoval Meidan-Shani and
• Nissan Ashkenazi

Beilstein J. Org. Chem. 2015, 11, 1332–1339, doi:10.3762/bjoc.11.143

• -tert-butyl peroxide [46]. As both methods utilize phosphorus starting materials which are not commercially available and a multistep synthesis is required for their preparation. As with oxaphospholane 4, compound 5 was reacted with 3 equiv of various Grignard reagents to produce phosphine oxides in

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• with the pentafluorobenzyl ester auxiliary, ester 210 was synthesized in a multistep process and then subjected to olefin metathesis to deliver the macrocycle using the Blechert catalyst 17. The treatment of the pentafluorophenyl benzyl ester 210 with catalyst 17 in toluene afforded the rigid