Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• -dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under simple and minimum manipulation, without purification

• mixture of hydrazide 3a and formylbenzoic acid 4 was heated at 120 °C (oil bath) using water as the solvent in the presence of SDS (10%) as the surfactant for 10 h leading to a 90% yield in 5a. To demonstrate the generality of this method, we next investigated the scope of this reaction under the

• above, we have never observed the formation of degradation products. (ii) The reaction was performed in water, in the presence of SDS (sodium dodecyl sulfate) as the surfactant. Based on previous studies [35], the most effective method for ensuring the solubility of reactants in water is the use of

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

• Vladimir A. Burilov,
• Guzaliya A. Fatikhova,
• Mariya N. Dokuchaeva,
• Ramil I. Nugmanov,
• Diana A. Mironova,
• Pavel V. Dorovatovskii,
• Victor N. Khrustalev,
• Svetlana E. Solovieva and
• Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

• vesicles [41]. The inflection point in the plot of EY λmax vs surfactant concentration should be treated as the CAC of the amphiphile [42]. As can be seen from Table 1 the CAC values determined by the two methods are significantly different, especially in the case of macrocycles 10a,b. These differences

• are assigned to the different natures of the used dyes. In the case of EY, which is a dianion at pH 7, the interaction with the dicationic calixarenes 10a,b results in the formation of a non-charged complex, which can be referred to a non-ionic surfactant. Generally, non-ionic surfactants possess

• dicationic calixarene 10b with ADP results in an uncharged complex, which can be referred to a non-ionic surfactant. At the same time, binding of 10b with ATP affords a negatively charged complex (Table 2, entries 9 and 10). Obviously the formation of the uncharged complex of 10b with ADP increases the

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• their work, they also utilized an important chemical attribute of cetylammonium bromide (CTAB) – namely, CTAB forms surfactant-assembled lipophilic nanoreactors stable in organic solvents, which could be used for regioselective functionalization of indenes. Therefore, they investigated the

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• minutes residence time this corresponds to an O2-transfer rate of roughly 0.25 mM min−1. Similarly high values could be obtained previously only under mechanically demanding reaction conditions or using surfactant-stabilised emulsions [7]. Varying the ratio of gas to liquid had no significant effect on

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• possible to observe an hydrophilic and an hydrophobic face, giving to CA its characteristic surfactant properties. CA is sold as a treatment for children and adults affected by bile acids synthesis disorders. Because of its abundance in bovine bile, CA is the precursor for UDCA. CDCA 3α,7α-Dihydroxy-5β

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• ratio by preventing the binding of the CCP on the DNA strand in the region remote from the PNA binding site, which is quite problematic in the detection of long DNA targets derived from PCR. On the other hand, addition of an organic solvent, such as N-methylpyrrolidinone [118], or a surfactant [119][120

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

• acetanilides or anilines were obtained as sole products [59]. To meet high expectations of environmentally low impact chemical reactions, Lipshutz and co-workers carried out the trifluoromethylation of heterocycles using aqueous micellar conditions based on the surfactant TPGS−750−M in water at room

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• ) [19][20], pulmonary surfactant-associated protein D (SP-D) [21], dendritic cell-specific ICAM-3-grabbing non-integrins 1 and 2 (DC-SIGN, also known as CD209; and DC-SIGNR, also known as CD299) [22][23], and mannose-binding protein (MBP) [24]. These CLECs exert their function through different

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• phosphonic acid function and its ability to be ionized in water render this group attractive to design the polar head group of anionic amphiphilic compounds [25][26] or polymeric-based amphiphilic derivatives [27]. This type of compound was used as surfactant to stabilize colloidal solutions of nanocrystals

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• the field: Challenge 1: coupling chemistry with vesicle dynamics. A special effort should be made to discover simple reaction networks whose products include amphiphiles or surfactant molecules that can be spontaneously absorbed by pre-existing vesicles, modifying their basic properties (e.g., their

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• ligand exchange protocol to introduce the thiolated saccharide molecules [20][21][22]. In this frame, the Turkevich method [23] is the most common protocol to produce citrate-capped spherical nanoparticles, with diameter size between 10 and 50 nm. Noteworthy, by employing surfactant or templating agents

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

• Markus Börgardts and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

• , 9, and 10 were mixed in ethanol in a ratio of 1:6:17 furnishing a perfect white emission with the CIE chromaticity coordinates of x = 0.33 and y = 0.33. This mixture was then mixed with TEOS (tetraethoxysilane), surfactant P123 (poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol/(EtO

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• rate for 1a (0.9 mol gPd−1 h−1) (Table 1, entry 9) [124], that confirms the effectiveness of the strategy. The continuous flow partial hydrogenation of 1-heptyne (2) to 1-heptene (2a), an additive for lubricants and a surfactant [125], was also reported using packed 2% Pd@Al2O3 catalyst, showing 49

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• at a high population cell density in B. subtilis [19][20]. In addition, the ComX pheromone promotes the production of surfactin A, a cyclic lipopeptide with antibiotic and biological surfactant activities (Figure 2A) [21][22]. Furthermore, the ComXnatto pheromone from B. subtilis subsp. natto

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• different naturally occurring and synthetic dienophiles. The synthesis of the Diels–Alder adduct from myrcene and acrylic acid, containing surfactant properties, was scaled-up in a plate-type continuous-flow reactor with a volume of 105 mL to a throughput of 2.79 kg of the final product per day. This

• continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reaction temperatures and shorter reaction times. Keywords: continuous processing; flow chemistry; renewable feedstock; surfactant

• the maleates 2d and 2e required up to 10 h reaction time at 140 °C to reach near-completion. The slowest reactions were observed using itaconic acid (2c) and the PEG containing acrylate 2g. Acrylic acid (2b) was selected for further study given our interest in products with surfactant properties, and

Formose reaction accelerated in aerosol-OT reverse micelles

• Makoto Masaoka,
• Tomohiro Michitaka and
• Akihito Hashidzume

Beilstein J. Org. Chem. 2016, 12, 2663–2667, doi:10.3762/bjoc.12.262

• molar ratio of water to surfactant, w (= [water]/[surfactant]), independent of the temperature. At w = 10, AOT and CTAB reverse micelles contain water pools of Rw ≈ 3 and 2 nm, respectively. On the other hand, Rw for TX is nearly constant at ca. 1 nm independent of w and temperature. The formose

• reactions were carried out at 60 °C by mixing a 100 mM solution of a surfactant in isooctane or in a mixed solvent of isooctane and 1-hexanol (5:1, v/v) and an aqueous solution containing 200 mM formaldehyde and 20 mM calcium hydroxide to adjust w to 10. After predetermined times, aliquots of the reaction

• formaldehyde), the values of Convmax and k2 were the largest at w = 5. These observations indicate that the contents are frequently exchanged between water pools of AOT reverse micelles during the reaction. On the interface between the surfactant molecules and the water phase in the reverse micelles, there is

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates

• Madhuri Vangala and
• Ganesh P Shinde

Beilstein J. Org. Chem. 2016, 12, 2086–2092, doi:10.3762/bjoc.12.197

• carbohydrate–protein interactions [25], ligation and surfactant properties [26][27]. Although p-nitrophenyl carbonates were extensively utilized in these reactions, the nucleophilicity of amidine bases towards these carbonates was not encountered so far. In continuation of our interest in carbohydrates [28][29

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• –surfactant combined catalysts (LASC) are another catalytic system which has been used for the three-component reaction of 2-alkynylbenzaldehydes, amines, and nucleophiles such as alkynes, nitromethane, or diethyl phosphonate in water under ultrasonic conditions [49]. As depicted in Scheme 23, the reaction of

• reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate. Lewis acid–surfactant combined catalysts for the one-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate. Lewis acid catalyzed cyclization of different Kabachnik–Fields adducts. Three-component

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• organic solvent, here 2 wt % solutions of selected surfactants in water were found to be excellent reaction media, providing an additional environmentally appealing feature to this protocol. While good yields could be obtained using the first generation surfactant PTS (polyoxyethanyl α-tocopheryl sebacate

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

• Chompoonut Rungnim,
• Sarunya Phunpee,
• Manaschai Kunaseth,
• Supawadee Namuangruk,
• Kanin Rungsardthong,
• Thanyada Rungrotmongkol and
• Uracha Ruktanonchai

Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251

• addition [2][3][4][5][6][7][8] and surfactant addition [9]. Complexation is one of the most utilized methods for enhancing the solubility of poorly soluble drugs. Cyclodextrins (CDs) are well-known macrocyclic oligosaccharides that are produced by enzymatic degradation of starch. CDs consist of 6, 7 and 8

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

• Shawna L. Balof,
• K. Owen Nix,
• Matthew S. Olliff,
• Sarah E. Roessler,
• Arpita Saha,
• Kevin B. Müller,
• Ulrich Behrens,
• Edward J. Valente and
• Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

• monomer liquidity and polyethylene glycol (PEG) based Emulgin® B3 as surfactant which was previously vigorously stirred for 1 h and then further emulsified using a sonication probe for another 5 min establishing the microemulsion. The emulsion polymerization reactions were conducted at less favorable

• determined solid contents often times exceeded the theoretical value derived from the amounts of monomer and surfactant added. This indicates that the catalysts have sufficient activity and thermal stability under the chosen conditions to promote complete ROMP of DCPD and the DCPD/COE monomer mixture. After

• average latex particle diameters range from 255 nm to 315 nm using the same concentration of surfactant throughout the series of experiments. The final average droplet diameter deviated less than 3% from the initial droplet size before polymerization where determined. Therefore, the size of the latex

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• ]. Addition of 2.5% of a surfactant such as sodium dodecyl sulfate (SDS) improves the spectral overlap with the absorption spectra (Figure 3a), and likely diminishes formation of potent aggregates. For the pyrene-based cluster 15a two main absorptions maxima at 391 and 292 nm were observed and safely assigned

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• ]. The amphiphilic organocatalysts, often referred to as hydroxyamino acid (serine or threonine) surfactant organocatalysts by the authors, were then applied with success in asymmetric anti-Mannich reactions and asymmetric aldol reactions of ketones and aromatic aldehydes, in the presence of water [54

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• position for protection of encapsulated molecules and maintaining the stability. CD nanocapsules were prepared without a stabilizing agent, e.g., surfactant, which means drug stability is mostly yielded by the polymeric wall. Therefore the polymer concentration that is probably related with the polymeric