Search results

Search for "volatiles" in Full Text gives 94 result(s) in Beilstein Journal of Organic Chemistry.

(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

Graphical Abstract
  • the addition product 15 at the second double bond in the reaction mixture was about 15% (Scheme 11). It should be noted that we failed to isolate the pure product 15 from reaction mixtures because of the small difference in boiling points and volatiles between isomers 14a,b and product 15
PDF
Album
Supp Info
Full Research Paper
Published 27 Feb 2024

Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs

  • Amina Moutayakine and
  • Anthony J. Burke

Beilstein J. Org. Chem. 2024, 20, 193–204, doi:10.3762/bjoc.20.19

Graphical Abstract
  • molecular sieves 3 Å. The reaction was left stirring at room temperature for several hours, and monitored by TLC. After consumption of the starting material (verified through TLC), the reaction mixture was filtered through a celite pad to remove the residual catalyst and molecular sieves. The volatiles were
PDF
Album
Supp Info
Full Research Paper
Published 31 Jan 2024

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

  • Christina Schøttler,
  • Kasper Lund-Rasmussen,
  • Line Broløs,
  • Philip Vinterberg,
  • Ema Bazikova,
  • Viktor B. R. Pedersen and
  • Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

Graphical Abstract
  • onto ice (400 mL), and acidified with aq HCl (20 mL, 6 M), resulting in an orange precipitate. The ice was allowed to melt, and the precipitate was filtered, washed with H2O (100 mL), and dissolved in EtOAc (200 mL), after which the volatiles were removed under reduced pressure yielding compound 29 as
PDF
Album
Supp Info
Full Research Paper
Published 15 Jan 2024

Unprecedented synthesis of a 14-membered hexaazamacrocycle

  • Anastasia A. Fesenko and
  • Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

Graphical Abstract
  • evaporation of the volatiles under reduced pressure, afforded a complex mixture containing only 7 mol % of macrocycle 5 according to the 1H NMR spectrum with the addition of a weighted amount of succinimide as a reference. Analogously, only 2 mol % of 5 were detected under the above conditions (1,4-dioxane
  • cyclizes to macrocycle 5 or undergoes hydrazinolysis to give bis-pyrazole 6 as the byproduct. The independent formation of bis-pyrazole 6 and macrocycle 5 was confirmed by refluxing an 81:19 mixture of 5 and 6 with N2H4·H2O (4.0 equiv) in 1,4-dioxane for 2 h followed by removal of the volatiles under
  • was stirred under reflux for 1 h, and the volatiles were removed under vacuum. The solid residue was triturated with saturated aqueous NaHCO3 until a suspension formed, and cooled to 0 °C. The precipitate was filtered, washed with ice-cold water, petroleum ether, ether, and dried to give a mixture of
PDF
Album
Supp Info
Full Research Paper
Published 15 Nov 2023
Graphical Abstract
  • for species recognition and mate choice. In the related frog family Mantellidae such functions of volatiles from males have been demonstrated [3], but no behavioral experiments involving semiochemicals have been performed so far within the hyperolid family. H. cinnamomeoventris also served as a model
PDF
Album
Supp Info
Full Research Paper
Published 16 Feb 2023

A new route for the synthesis of 1-deazaguanine and 1-deazahypoxanthine

  • Raphael Bereiter,
  • Marco Oberlechner and
  • Ronald Micura

Beilstein J. Org. Chem. 2022, 18, 1617–1624, doi:10.3762/bjoc.18.172

Graphical Abstract
  • solvent and all volatiles were removed under reduced pressure and the oily residue was dissolved in dichloromethane containing 4% triethylamine. Subsequently, the mixture was washed three times with brine, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified via silica
  • methanol (20 mL), then 5% hydrochloric acid (5 mL) was added and stirred for 2 hours at 50 °C. After complete deprotection (TLC reaction control!), the solvent and all volatiles were removed under reduced pressure and the crude residue was suspended in dichloromethane (6.5 mL). Afterwards, di-tert-butyl
PDF
Album
Supp Info
Full Research Paper
Published 29 Nov 2022

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

  • Valentin H. K. Fell,
  • Joseph Cameron,
  • Alexander L. Kanibolotsky,
  • Eman J. Hussien and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

Graphical Abstract
  • the ring closure proceeded on one side of the molecule. It was assumed that this species precipitated, preventing further reaction. We thus turned to a ‘hot’ Friedel–Crafts acylation, in which the reaction mixture was refluxed after the addition of oxalyl chloride, followed by removal of the volatiles
PDF
Album
Supp Info
Full Research Paper
Published 01 Aug 2022

The stereochemical course of 2-methylisoborneol biosynthesis

  • Binbin Gu,
  • Anwei Hou and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 818–824, doi:10.3762/bjoc.18.82

Graphical Abstract
  • the genes for the biosynthesis of 1 are present in about half of the species [28], which is reflected by the frequent detection of 1 among the volatiles emitted by a large number of streptomycetes and closely related bacteria [3][4][5][6][7]. A series of side products of the 2MIBS has been identified
PDF
Album
Supp Info
Letter
Published 08 Jul 2022

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

  • Songeziwe Ntsimango,
  • Kennedy J. Ngwira,
  • Moira L. Bode and
  • Charles B. de Koning

Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152

Graphical Abstract
  • precipitate formed. The solvent was filtered and the resulting white solid was dissolved in EtOAc and washed successively with water and brine. The organic layer was dried over MgSO4 and the volatiles were removed under reduced pressure. The resulting biaryl oximes were used without further purification. A
  • for 30 min and then was quenched with ice-water (1.5 mL). A precipitate formed and was filtered, and washed with water. The solid was then taken up with ethyl acetate, dried over MgSO4 and the volatiles were removed under reduced pressure. [1,3]Dioxolo[4,5-j]phenanthridine-2,3-dione was obtained as a
PDF
Album
Supp Info
Full Research Paper
Published 08 Sep 2021

Synthesis of O6-alkylated preQ1 derivatives

  • Laurin Flemmich,
  • Sarah Moreno and
  • Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

Graphical Abstract
  • . Compound 3 [29][30][31] (200 mg, 0.720 mmol) was added and the mixture was heated to 110 °C in a pressure tube for 24 h. After neutralization with glacial acetic acid the volatiles were removed in vacuo. The crude product was dry-loaded onto silica gel and purified via flash column chromatography (5–20
PDF
Album
Supp Info
Full Research Paper
Published 02 Sep 2021

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

  • Christin Walther,
  • Pamela Baumann,
  • Katrin Luck,
  • Beate Rothe,
  • Peter H. W. Biedermann,
  • Jonathan Gershenzon,
  • Tobias G. Köllner and
  • Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

Graphical Abstract
  • , Institute of Forest Sciences, University of Freiburg, Fohrenbühl 27, 79252 Stegen-Wittental, Germany 10.3762/bjoc.17.118 Abstract Plant volatiles play a major role in plant–insect interactions as defense compounds or attractants for insect herbivores. Recent studies have shown that endophytic fungi are
  • also able to produce volatiles and this raises the question of whether these fungal volatiles influence plant–insect interactions. Here, we qualitatively investigated the volatiles released from 13 endophytic fungal species isolated from leaves of mature black poplar (Populus nigra) trees. The volatile
  • of the fungus-derived volatiles like 2-phenylethanol, 3-methyl-1-butanol and the sesquiterpene (E)-β-caryophyllene, are known to play a role in direct and indirect plant defense, the emission of volatiles from endophytic microbial species should be considered in future studies investigating tree
PDF
Album
Supp Info
Full Research Paper
Published 22 Jul 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
PDF
Album
Review
Published 18 May 2021

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

  • Ke Wu,
  • Yichen Ling,
  • An Ding,
  • Liqun Jin,
  • Nan Sun,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

Graphical Abstract
  • carbon and filtered. Then, toluene and other potential volatiles were removed, the residue crystallized from a toluene and heptane solvent mixture to afford 36.0 g (97%) of the desired thioamide 2e as yellow crystalline solid. With the proof that ethylene glycol can efficiently decompose compound A and
  • amide was observed. To the cooled mixture was added EtOH (2 mL, excess) and the resulting mixture was heated at reflux for 2 h. Then, the volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate followed by aqueous workup. The organic phase was dried over anhydrous MgSO4
PDF
Album
Supp Info
Full Research Paper
Published 09 Apr 2021

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

  • Anuj Kumar Chhalodia and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

Graphical Abstract
  • -(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The DMSP analogues were also degraded, resulting in the release of allylated sulfur volatiles known from garlic. For unknown
  • sativum; allyl sulfides; 3-(dimethylsulfonio)propanoate; Roseobacter; volatiles; Introduction The name of the allyl group has been introduced by Wertheim in 1844 when he investigated the constituents of garlic oil and derives from the botanical name of garlic (Allium sativum) [1]. During that time, the
  • -volatile precursor that is stored in garlic and related plants and only degraded into sulfur volatiles upon wounding by the pyridoxal phosphate (PLP) dependent alliinase (Scheme 1B) [7]. This initial enzyme-catalyzed reaction yields one equivalent of allylsulfenic acid (10), pyruvic acid (11), and ammonia
PDF
Album
Supp Info
Full Research Paper
Published 26 Feb 2021

Identification of volatiles from six marine Celeribacter strains

  • Anuj Kumar Chhalodia,
  • Jan Rinkel,
  • Dorota Konvalinkova,
  • Jörn Petersen and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

Graphical Abstract
  • , Inhoffenstraße 7b, 38124 Braunschweig, Germany 10.3762/bjoc.17.38 Abstract The volatiles emitted from six marine Rhodobacteraceae species of the genus Celeribacter were investigated by GC–MS. Besides several known compounds including dimethyl trisulfide and S-methyl methanethiosulfonate, the sulfur-containing
  • Celeribacter strains are capable of methionine and DMSP degradation to widespread sulfur volatiles, but the analysis of trace compounds in natural samples must be taken with care. Keywords: GC–MS; isotopes; Roseobacter; sulfur metabolism; volatiles; Introduction Bacteria from the roseobacter group belong to
  • interaction. Isotopic labeling experiments demonstrated that also in laboratory cultures roseobacter group bacteria efficiently degrade DMSP into sulfur volatiles [22][23], but also from other sulfur sources including 2,3-dihydroxypropane-1-sulfonic acid (DHPS, Scheme 1C) labeling was efficiently incorporated
PDF
Album
Supp Info
Full Research Paper
Published 11 Feb 2021

Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives

  • Alexander Leslie,
  • Thomas S. Moody,
  • Megan Smyth,
  • Scott Wharry and
  • Marcus Baumann

Beilstein J. Org. Chem. 2021, 17, 379–384, doi:10.3762/bjoc.17.33

Graphical Abstract
  • biphasic plug flow pattern as the material progressed through a tubular flow coil reactor (rt, 33 min residence time). Upon separation of the phases and evaporation of the volatiles, the desired products were obtained in generally high yields. It was found that both approaches worked well for the tested
PDF
Album
Supp Info
Full Research Paper
Published 04 Feb 2021

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

  • Wilfred J. M. Lewis,
  • David M. Shaw and
  • Jeremy Robertson

Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31

Graphical Abstract
  • water bath, and stirring continued for 3.5 h. The mixture was concentrated, with azeotropic removal of ethanol and other volatiles with toluene, to afford the title compound as a caramel-colored solid (561 mg) that was used directly in the subsequent acylation and oxidation steps [the NMR spectra
  • via cannula over 15 min. The reaction mixture was allowed to warm to rt over 14 h, the volatiles were removed, then pyridine (2 mL) and activated charcoal (5 g) were added. The resulting slurry was part-purified by column chromatography (dichloromethane → methanol) and the product-containing fractions
PDF
Album
Supp Info
Full Research Paper
Published 02 Feb 2021

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

  • Romain Pierre,
  • Anne Brethon,
  • Sylvain A. Jacques,
  • Aurélie Blond,
  • Sandrine Chambon,
  • Sandrine Talano,
  • Catherine Raffin,
  • Branislav Musicki,
  • Claire Bouix-Peter,
  • Loic Tomas,
  • Gilles Ouvry,
  • Rémy Morgentin,
  • Laurent F. Hennequin and
  • Craig S. Harris

Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

Graphical Abstract
  • deprotection with concomitant ionic reduction of the pyridine–OAt bond of the intermediate 23 was achieved by dissolving the residue in the TFA/TES/H2O (3:1:1 v/v/v) mixture; 3) removal of the volatiles by sparging followed by purification of the residue by mass-triggered preparative LC–MS to afford the final
PDF
Album
Supp Info
Full Research Paper
Published 18 Jan 2021

On the mass spectrometric fragmentations of the bacterial sesterterpenes sestermobaraenes A–C

  • Anwei Hou and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2020, 16, 2807–2819, doi:10.3762/bjoc.16.231

Graphical Abstract
  • related techniques the volatiles from many bacteria, fungi, and plants have been investigated [8][9][10], which provides rapid information about the production of volatile terpenes. This information is particularly useful in the combination with the genome sequences of the producing organism, because it
PDF
Album
Supp Info
Letter
Published 19 Nov 2020

3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly Ithomia salapia

  • Florian Mann,
  • Daiane Szczerbowski,
  • Lisa de Silva,
  • Melanie McClure,
  • Marianne Elias and
  • Stefan Schulz

Beilstein J. Org. Chem. 2020, 16, 2776–2787, doi:10.3762/bjoc.16.228

Graphical Abstract
  • multiple factors, notably non-random mating based on color pattern and/or sexual pheromones [6][7][8]. Determining whether the closely related subspecies of I. salapia differ in the chemical composition of volatiles is, therefore, of great interest. All male ithomiine butterflies, including Ithomia
PDF
Album
Supp Info
Full Research Paper
Published 16 Nov 2020

Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes

  • Maximillian Heidrich and
  • Herbert Plenio

Beilstein J. Org. Chem. 2020, 16, 2080–2086, doi:10.3762/bjoc.16.175

Graphical Abstract
  • of celite and the celite washed with a small amount of DCM. The volatiles of the filtrate were evaporated under reduced pressure and the residue dried in vacuo, to yield complex 1 (62 mg, 0.039 mmol, 92% yield) as white solid. 1H NMR (500 MHz, CD2Cl2) δ 7.54–7.48 (m, 8H), 7.46–7.39 (m, 8H), 7.08–6.93
PDF
Album
Supp Info
Full Research Paper
Published 26 Aug 2020

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

  • Paola Vitale,
  • Luciana Cicco,
  • Ilaria Cellamare,
  • Filippo M. Perna,
  • Antonio Salomone and
  • Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

Graphical Abstract
  • separation of the organic layer from water, and removal of the volatiles under reduced pressure. To examine the scope and limitation of this transformation, various functionalized phenacyl halides (1c–i) were tested as substrates. As can be seen from the results compiled in Scheme 3, the reaction is amenable
PDF
Album
Supp Info
Full Research Paper
Published 05 Aug 2020

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

  • Péter Bagi,
  • Réka Herbay,
  • Nikolett Péczka,
  • Zoltán Mucsi,
  • István Timári and
  • György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

Graphical Abstract
  • : 0.17 g, 1k: 0.17 g, 1l: 0.19 g, 5: 0.18 g, 8: 0.21 g) in 1.0 mL of dichloromethane, 0.094 mL (1.1 mmol) of oxalyl chloride was added dropwise at 0 °C in a sealed tube. The reaction mixture was stirred for 15 minutes, then the volatiles were evaporated to remove the solvent and the excess of the oxalyl
PDF
Album
Supp Info
Full Research Paper
Published 22 Apr 2020

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

  • Akihiro Yuasa,
  • Kazunori Nagao and
  • Hirohisa Ohmiya

Beilstein J. Org. Chem. 2020, 16, 185–189, doi:10.3762/bjoc.16.21

Graphical Abstract
  • transferred to the vial (mixture A) containing the copper complex with toluene (0.6 mL). After 12 h stirring at 80 °C, the reaction mixture was diluted with diethyl ether (1 mL). The reaction mixture was filtered through a short plug of aluminum oxide (1 g) with diethyl ether as an eluent. After volatiles
PDF
Album
Supp Info
Letter
Published 07 Feb 2020

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

  • Xinlu Chen,
  • Tobias G. Köllner,
  • Wangdan Xiong,
  • Guo Wei and
  • Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

Graphical Abstract
  • relatedness to bacterial TPSs. The biological role of the volatile terpenoids produced by the plasmodia of P. polycephalum is discussed. Keywords: amoebae; evolution; terpene synthases; volatiles; Introduction Volatile organic compounds (VOCs) are used by many living organisms as chemical languages for
  • and gene expression patterns, the products of most DdTPSs were released as volatiles from D. discoideum at the multicellular developmental stage [14][15]. TPS genes previously were known to exist only in bacteria, fungi, and plants [13][17][18]. The identification of TPS genes in dictyostelid social
  • for studying a diversity of topics [19][20][21], ranging from cytoplasmic streaming to primitive intelligence [22]. In a manuscript deposited at arXiv [23], it was described that complex mixtures of volatiles including some terpenoids were detected from the headspace of P. polycephalum using two
PDF
Album
Supp Info
Full Research Paper
Published 28 Nov 2019
Other Beilstein-Institut Open Science Activities