The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• . Jung and Shinde, on the other hand, synthetized a supramolecular acid catalyst 14 combining β-cyclodextrins with succinic acid and tested it in a GBB reaction between isatin (15), indazol-3-amine (16) and pentyl isocyanide (17), yielding, after a ring expansion triggered by a retro-aza-ene reaction via

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• was as follows: 3.00 g of α-cyclodextrin, 3.33 g of β-cyclodextrins and 4.05 g of γ-cyclodextrins (3.30 mmol) were dissolved in 10 mL of DMF (in three different round-bottomed flasks). After complete dissolution of the cyclodextrins, 2.00 g (13 mmol) of CDI as cross linker were added to each batch

• carbonyldiimidazole. For example, for the 1:4 ratio synthesis, 3.38 g of α-cyclodextrin, 3.75 g of β-cyclodextrins and 4.56 g of γ-cyclodextrins were placed inside a 50 mL jar containing 10 zirconia balls. The amount of CDI added in each batch to maintain the 1:4 molar ratio was 2.25 g. After 3 h of sun wheel

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

• Margareta Sohora,
• Leo Mandić and
• Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

• initiated by phthalimides in organic synthesis [14][15]. Furthermore, H-abstractions were investigated in inclusion complexes, in the cavity of β-cyclodextrins (β-CD) [16]. We found out that H-abstraction reactions were about ten times more efficient in the β-CD complexes than in the isotropic solution, and

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

• Gábor Benkovics,
• Mihály Bálint,
• Éva Fenyvesi,
• Erzsébet Varga,
• Szabolcs Béni,
• Konstantina Yannakopoulou and
• Milo Malanga

Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

• ). Analysis of regiochemistry of homo-difunctionalized β-cyclodextrins by full NMR spectral assignment NMR structural analysis was performed on the ditosyl derivatives, precursors of the corresponding diazido compounds. There are two factors that warrant large signal dispersion in the 1H NMR spectra of

• being more deshielded (Δδ ≈ 0.026 ppm) than the others (Supporting Information File 1, Figure S14). The 6A,6B-regioisomer is also the least water-soluble. Consequently, structural verification was solely based upon the analysis of the ditosyl precursors, as discussed above. Hetero-difunctionalized β

• -cyclodextrins The hetero-difunctionalization was performed as a stepwise introduction of an azido and a tosyl moiety into the primary rim of β-CD, in order to obtain a versatile intermediate which allows independent manipulation of two orthogonal functions on the β-CD scaffold. Although the selectivity of the

Phosphodiester models for cleavage of nucleic acids

• Satu Mikkola,
• Tuomas Lönnberg and
• Harri Lönnberg

Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

• departure of the 5´-linked nucleoside by a factor of 107. The mechanistic proposal has partly been based on Breslow’s studies on hydrolysis of 4-tert-butylcatechol cyclic phosphate by regioisomers of β-cyclodextrins bearing two imidazole groups [60]. This reverse reaction of the cyclization of 4-tert

Influence of the milling parameters on the nucleophilic substitution reaction of activated β-cyclodextrins

• László Jicsinszky,
• Kata Tuza,
• Giancarlo Cravotto,
• Andrea Porcheddu,
• Francesco Delogu and
• Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 1893–1899, doi:10.3762/bjoc.13.184

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

• -glycolic acid)-PLGA NPs, liposomes), many examples in literature report on the development of gold-based glyco nanoparticles as efficient system to delivery payloads. In this contest, AuNPs modified with lactose moieties and β-cyclodextrins have been reported by Vargas-Berenguel et al. [87]. The authors

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• aqueous medium, which precludes any response to light excitation. Keywords: β-cyclodextrins; fluorescence; photodynamic therapy; photosensitizers; singlet oxygen; xanthene; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides able to form host–guest inclusion complexes with drugs and this

• have the typical fingerprint signals for the asymmetric, 6-monosubstituted β-cyclodextrins. Generally two sets of signals can be identified (Figure 4 and Figure S20 in Supporting Information File 1): the first set comprises the aromatic protons of the eosin dyes that are observed between 6.35–7.75 ppm

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• . Amphiphilic β-cyclodextrins substituted with 7 dodecylsulfide groups on the primary side and 7 oligo(ethylene glycol) units on the secondary side were obtained via a straightforward three step synthesis as described [27][30]. A thin film of these amphiphiles was obtained by evaporation of a chloroform

Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

• Eva Bednářová,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2016, 12, 349–352, doi:10.3762/bjoc.12.38

• solid surfaces by CDs. Among the solid surfaces, to which CDs were attached, are sorbents for separation techniques or waste water treatment [8] or nanoparticles [6]. In our work, we focused on the preparation of sulfanyl-group-containing CD derivatives – 6I-deoxy-6I-(ω-sulfanyl-alkylene-sulfanyl)-β

• -cyclodextrins (β-CD-S-X-SH) – which can be attached to a gold surface [9][10] or a polydopamine-coated surface [11]. It has been already described that the surface coverage of self-assembled monolayers of CD derivatives on gold depends substantially on the linker between the sulfanyl group and the CD

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• . We have previously reported urethane-crosslinked CD polymers, which were prepared by reacting heptakis(2,6-di-O-methyl)-β-cyclodextrins (DM-β-CDs) with aromatic diisocyanates such as 4,4’-methylenebis(phenyl isocyanate) (MDI) and 1,4-phenylene diisocyanate (PDI) [18]. Although MDI- or PDI-crosslinked

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• studied for complexation with RF to achieve its stabilization [111][112][113][114][115][116][117]. In a comparative study of complexation between α- and β-cyclodextrins with RF, β-cyclodextrin was found to form more stable inclusion complexes with RF [116]. The formation of strong and stable inclusion

Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

• Christopher Kremer,
• Gregor Schnakenburg and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 814–824, doi:10.3762/bjoc.10.77

• shallow binding sites that bind non-polar substrates via dispersive interactions. Hence, we wanted to take this approach one step further by using β-cyclodextrins as another class of macrocyclic compounds that are very well-known for their excellent recognition properties towards non-polar substrates [25

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• ]. In our recent reports on the interaction between CDs and the organophosphorus insecticide 1 we gave an account of the X-ray crystal structures and thermal decomposition profiles of two solid inclusion complexes between permethylated α- and β-cyclodextrins, hexakis(2,3,6-tri-O-methyl)-α-CD (TRIMEA

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• delivery Swellable cyclodextrin-based nanosponges were purposely prepared for protein delivery by using a different synthetic route. New swellable cyclodextrin-based poly(amidoamine) nanosponges (PAA-NS) [44], named NS 10 and NS 11, were synthesised by cross-linking β-cyclodextrins with either 2,2-bis

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• , the stoichiometry appears to be less than 1:1, the binding constant is somewhat lower, and the thermodynamic parameters are different (notably, ΔS is negative). This observation can be explained by steric hindrance in the trivalent host–guest complex: apparently, three β-cyclodextrins are too large to

Influence of cyclodextrin on the solubility of a classically prepared 2-vinylcyclopropane macromonomer in aqueous solution

• Helmut Ritter,
• Jia Cheng and
• Monir Tabatabai

Beilstein J. Org. Chem. 2012, 8, 1528–1535, doi:10.3762/bjoc.8.173

• studied area [7][8]. β-Cyclodextrins (β-CDs) are cyclic oligomers consisting of seven α-1,4-glycosidically linked glucopyranose units which are present in the chair conformation [9][10][11][12]. The molecule resembles a truncated cone with approximate Cn-symmetry [13]. The cyclic 1,4-linked glucose units

Chiral recognition of ephedrine: Hydrophilic polymers bearing β-cyclodextrin moieties as chiral sensitive host molecules

• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 1516–1519, doi:10.3762/bjoc.7.177

• , the use of cyclodextrins as chiral host molecules has been the focus of attention for many investigations [6][7]. β-Cyclodextrins (β-CDs) are widely used as selectors for the resolution of enantiomers of chiral drugs in both separation techniques and spectroscopic methods [8][9][10][11][12][13][14

Cross-metathesis of allylcarboranes with O-allylcyclodextrins

• Ivan Šnajdr,
• Zbyněk Janoušek,
• Jindřich Jindřich and
• Martin Kotora

Beilstein J. Org. Chem. 2010, 6, 1099–1105, doi:10.3762/bjoc.6.126

• carried out according to the previously reported procedures [8]. O-Allylcyclodextrins 2 were prepared by allylation of β-cyclodextrins under various reaction conditions (2I-O-allyl-β-cyclodextrin for 2a [22], 3I-O-allyl-β-cyclodextrin for 2b [23], and 6I-O-allyl-β-cyclodextrin for 2c) followed by