Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• was 88% and for compound 5 70%. Preparation of compounds 6-Methyluracil-5-ammonium sulfate (2). The spectral characteristics are given in [13]. 1,3,6-Trimethyluracil-5-ammonium sulfate (5). The spectral characteristics are given in [13]. General procedure for the hydrolysis of uracils 2 and 5. As

• H2SO4 was added and the reaction mixture was stirred at the same temperature for 1 h and cooled. The precipitated crystals were filtered off, washed with cold distilled water to pH 6–7 (2 × 5 mL), and recrystallized from ethanol. 5-Hydroxy-6-methyluracil (3). Yield 98%. The spectral characteristics are

• given in [13]. 5-Hydroxy-1,3,6-trimethyluracil (6). Yield 88%. The spectral characteristics are given in [13]. 2-Pyridinyl sulfate (8): a) In a 150 mL three-necked flask equipped with a reflux condenser and a mechanical stirrer, to a solution of 0.06 mol of pyridine in 20 mL of azeotropic solution of

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• relative to NH2. Scheme 3 shows the reaction of o-anisidine with SeO2. Similar to aniline, a large quantity of o-anisidine was transformed into polymer, labelled polymer 2. The UV–vis and FTIR spectra of polymer 2 are shown in Figures S1 and S2, Supporting Information File 1, respectively. The spectral

• characteristics were consistent with those of the emeraldine free base, as discussed above for polymer 1. In the next step, the supernatant was analyzed by TLC and subsequently purified by column chromatography. Attempts to isolate the organoselenium compounds were unsuccessful due to the similar retention factor

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• ]. However, until now there was no information about the structure and spectral characteristics of the obtained compounds. We have now synthesized these compounds, fully characterized them, and studied some of their transformations. We found that not only (E)-butene 1a but also (Z)-butene 1b reacted with

• (Z)-isomer and ≈11 Hz for (E)-isomer). The 2-chloro-1,1,1,4,4,4-hexafluorobut-2-enes were first described by Haszeldine in 1952 [1] and only then the (Z)-isomer. We report here the isolation and complete characterization of both (E)- and (Z)-isomers. The spectral characteristics of product 6b

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• -diaminopyrazoles 4a–c (Scheme 2). The structures of compounds 4a–c were confirmed by 1H and 13C NMR spectroscopy data, as well as high-resolution mass spectrometry (HRMS). Compound 4a was previously obtained by another method [18]. The spectral characteristics of diaminopyrazole 4a reported in [18] correspond to

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Valerii V. Tkachev,
• Andrey N. Utenyshev,
• Olga Yu. Karlutova,
• Alexander D. Dubonosov,
• Vladimir A. Bren,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2020, 16, 1820–1829, doi:10.3762/bjoc.16.149

• photochromic properties of 2-benzo[b]thienylfulgides [22]. UV irradiation of acetonitrile solutions of these compounds results in the electrocyclic hexatriene–cyclohexadiene rearrangement of the ring-opened isomers O into the colored ring-closed ones C (Scheme 1) which exhibit enhanced spectral characteristics

Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• doublets at 5.21 ppm (3J = 2.1 and 3J = 6.6 Hz). This was the result of coupling with the nonequivalent protons of the CH2Se group. Similar spectral characteristics were observed for other six-membered 2,3-dihydro-1,4-thiaselenin-2-yl derivatives [31][32][38][40]. Thus, the reaction of thiaselenole 1 with

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• ; porphyrin; spectral characteristics; synthesis; Introduction Porphyrins belong to a broad class of the natural and synthetic macroheterocyclic compounds with unique properties. They play an important role in photosynthesis [1], catalysis [2][3], nonlinear optics [4][5], polymer synthesis [6] and energy

From dipivaloylketene to tetraoxaadamantanes

• Gert Kollenz and
• Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

• corresponding tetrachlorotetraoxaadamantanes together with an X-ray crystal structure of the diphenyltetrachloro derivative 1g (reaction 6 in Scheme 1) [9]. A tetraarsatetraoxaadamantane [10] also has been reported, and 13C NMR spectral characteristics of tetraoxa-, tetrathia-, and tetraselenaadamantanes have

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• experienced increased attention in chemistry [6][7][8][9][10] and life science applications [11][12][13]. On the grounds of high fluorescence quantum yield, narrow spectral characteristics, and sufficient chemical stability, BODIPYs have been utilized for example as laser dyes, tags of small organic molecules

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• characteristics of the linkers; conditions of azide- and alkyne-modified MGBs synthesis and mass spectral characteristics of the obtained products (11–14); synthesis of fluorescent probes based on polyamides and their characteristics (Table S1); synthesis of modified oligonucleotides containing alkyne group (15

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• give 9-mer 21 in 84% overall yield. All spectral characteristics concurred to the expected structural integrity of 21 (see Supporting Information File 1). Finally, a 27-mer mannosylated G(1)-dendrimer 23 was similarly prepared using an accelerated convergent strategy (Scheme 5). This time, the

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

• Wentao Gao,
• Jia Liu,
• Yun Jiang and
• Yang Li

Beilstein J. Org. Chem. 2011, 7, 210–217, doi:10.3762/bjoc.7.28

• compounds exhibited similar spectral characteristics. Elemental analysis was in agreement with the theoretical values. As shown in Table 1, with the exception of 3g (entry 7), a series of 2-(benzofuran-2-yl)quinoline-3-carboxylic acid derivatives 3 were readily prepared under mild reaction conditions in

Synthesis of 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles

• Yang Li and
• Wentao Gao

Beilstein J. Org. Chem. 2010, 6, 966–972, doi:10.3762/bjoc.6.108

• -molecular ion peak at m/z 367.1 ([M+H]+). The obtained elemental analysis values are in agreement with theoretical values. The other synthesized compounds exhibited similar spectral characteristics. Conclusion A straightforward synthesis of 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles (3a–5c

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• adduct in 63% yield following conventional work-up and chromatography. Although an X-ray structure determination was not carried out, the tlc and spectral characteristics provided strong evidence that adduct 6e had the same C4/5 stereochemistry as 6a, b. For example, the coupling constant between H-5/H-6

Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• spectral characteristics of the isolated products are summarised in Table 1. We found that all newly prepared conjugates display only one peak in the fluorescence spectrum in methanol. The process of conjugation did not cause a shift in the absorption and fluorescence maxima of our compounds, in comparison

• labeled nucleosides, (i) PPh3, acetonitrile, (ii) HOBT, DCC, dioxane Hydrolysis of proposed intermediates I(a-c)-IV(a-c) Preparation of ferrocene labeled uridine Isolated yields and spectral characteristics of coumarin labeled nucleosides 11–12 a Supporting Information Supporting Information File 4