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

• based on stereoselective interactions of CDs with guest molecules (chiral separations, asymmetric catalysis, enzyme mimics) [20]. However, if the target is only the side-selectivity of difunctionalization, pseudoenantiomeric mixtures of the regioisomers can be used [21]. For CD-based multifunctional

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

• Tilman Lechel,
• Roopender Kumar,
• Mrinal K. Bera,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

• be due to their low solubility in ethereal solvents at low temperatures – a problem that could only partially be solved by use of DMF as cosolvent. The yields of β-ketoenamides KE44–46 are only in the range of 25%, but the three-component approach to unique multifunctional products is nevertheless

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

• MS measurements was provided by the Russian Foundation for Basic Research (grants No. 18-29-04029 and 18-02-00653). IVT is also grateful to Volkswagenstiftung (Project «Multifunctional molecular materials – bridging magnetism and luminescence»). The authors are thankful to Dr. Yu. Belousov (LPI) for

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• regenerates the catalyst. As it is a fast-growing field, this review will be mainly focused on an overview of the recent advances concerning the development of organic and organometallic photoredox catalysts for the photoreticulation of multifunctional monomers for a rapid and efficient access to 3D polymer

• photoreticulation processes of multifunctional radical (acrylate, methacrylate…) or cationic (epoxide) monomers. Undoubtedly, the advantage of the photoredox catalysis approach is the high efficiency of the system to initiate the polymerization upon mild light irradiation conditions (as the catalyst is regenerated

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• , adhesion inducer and cell movement inhibitory effect, [4Lys(Bu)]-GnRH-III(Dau=Aoa) proved to be the best candidate in our study for application in the targeted melanoma therapy as a multifunctional antitumor and antimetastatic drug delivery system. Schematic structure of Dau-conjugated GnRH-III or its

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• )disulfide (empirical name – dichlorodiphenyl disulfide, abbreviated as DDDS), 2,6-lutidine and acridinium salts under blue LED irradiation, providing access to precious, non-commercially available and multifunctional amine building blocks in one step (Scheme 2) [40]. The group demonstrated the synthesis of

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• and co-workers [20][21][22][23][24][25][26][27][28][29][30][31] have built a multifunctional controllable gel system, which utilized L-glutamic lipid to construct nanofibers, nanotwists, and nanotubes with the property of chirality. Azobenzene, which is structurally photosensitive, is widely chosen to

Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• cannot be regarded as a classical secondary alcohol group but as a hemiacetal OH, it can be successfully involved in Mitsunobu reactions to achieve 1-O-acyl glycoses. Thus, searching for an efficient protocol for the preparation of complex, multifunctional glycosyl esters in the context of the total

• photoswitchable azobenzene α-D-mannoside 47 (Scheme 9) [46]. Notably, in this reaction, traces of an anomeric mixture of the respective furanoside 48 were detected. The Mitsunobu synthesis of aryl glycosides was also applied to p-nitrophenol [47], naphthols [48][49], or multifunctional phenols [27][50]. Such

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• . Seven conjugates with no cytotoxic effect on either cell types were identified, with two more conjugates with significantly milder cytotoxic effect. Based on these results, the monomeric GnRH-III(Dau=Aoa), the two multifunctional conjugates, [4Lys(Dau=Aoa)]-GnRH-III(Dau=Aoa) and GnRH-III(Dau=Aoa-K(Dau

• =Aoa)), the modified GnRH-III containing compound, ([4N-MeSer]-GnRH-III(Dau), the dimeric {GnRH-III(Dau-C)}2 and the two multifunctional conjugates containing two different chemotherapeutic drugs, GnRH-III(Mtx-K(Dau=Aoa)) and [4Lys(Mtx)]-GnRH-III(Dau=Aoa) are considered ideal compounds for tumor

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• Pseudomonas aeruginosa. A series of chemoecological studies of P. aeruginosa has uncovered multifunctional roles of this quinolone class as antibacterial, antifungal, iron-chelating, and autoinducer agents to assist the survival of the producing organisms [32]. Additionally, drug discovery attempts have

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

• artificial cleaving agents that have enzyme-like catalytic properties but are more robust. pH-Rate profiles, linear free energy relationships and kinetic heavy atom isotope effects are the experimental approaches that are, together with construction of multifunctional cleaving agents, most extensively used

¹⁵N-Labelling and structure determination of adamantylated azolo-azines in solution

• Sergey L. Deev,
• Alexander S. Paramonov,
• Tatyana S. Shestakova,
• Igor A. Khalymbadzha,
• Oleg N. Chupakhin,
• Julia O. Subbotina,
• Oleg S. Eltsov,
• Pavel A. Slepukhin,
• Vladimir L. Rusinov,
• Alexander S. Arseniev and
• Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

• ][1,2,4]triazine 4 (Figure 1A, Triazavirin®) was approved in Russia for the treatment of influenza [9]. This drug targets the viral protein haemagglutinin. The incorporation of an adamantyl moiety in azolo-azine structures could lead to the development of new multifunctional antiviral drugs. Previously

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• supramolecular polymers [9] multifunctional molecules are assembled in a regular manner. To avoid branching, monosubstituted CDs are required for a linear supramolecular polymer of CDs with guest groups attached. Monosubstituted derivatives of CDs [10] include three regioisomers, namely 2I-O-, 3I-O-, and 6I-O

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• polymerization [21]. This technique consists in the application of a multifunctional macromolecule. The number of initiating groups on this macromolecule codes the number of arms in the synthesized star polymer. Moreover, by extension of ω-chain ends on the periphery of the star we can easily introduce a next

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• –Hillman reaction The Morita–Baylis–Hillman reaction (MBH) employs olefins, tertiary amine catalysts and electrophile aldehydes to produce multifunctional products. Mack et al., found a significant enhancement in the rate of a Morita–Baylis–Hillman (MBH) reaction under ball milling conditions (Scheme 5

Phenylsilane as an effective desulfinylation reagent

• Wanda H. Midura,
• Aneta Rzewnicka and
• Jerzy A. Krysiak

Beilstein J. Org. Chem. 2017, 13, 1513–1517, doi:10.3762/bjoc.13.150

• were connected with the synthesis and further conversion of multifunctional cyclopropanes, where the carboxylate moiety was present in close proximity to sulfinyl and phosphoryl substituents [18][19][20]. A selective and effective method of the independent conversion of each of these substituents is

Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

• Yonglei Du,
• Jian Li,
• Kerong Chen,
• Chenglin Wu,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2017, 13, 1342–1349, doi:10.3762/bjoc.13.131

• mechanism was proposed in Scheme 3. The multifunctional organocatalyst d has a chiral scaffold including a thiourea moiety and an amino group. Both the 3-substituted oxindoles 1 and nitrovinylacetamide (2a) that participate in this reaction are activated simultaneously via multiple hydrogen bonds. In

Strategies in megasynthase engineering – fatty acid synthases (FAS) as model proteins

• Manuel Fischer and
• Martin Grininger

Beilstein J. Org. Chem. 2017, 13, 1204–1211, doi:10.3762/bjoc.13.119

• antineoplastic doxorubicin and by the antiparasitic avermectin (Figure 1a) [1]. PK are assembled from acyl-coenzyme A (acyl-CoA) units via a series of Claisen-type condensation reactions catalyzed by polyketide synthases (PKS) (Figure 1b). PKS occur as large multifunctional enzymes, termed megasynthases, which

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• -containing polymers while simplifying the complexity induced by multifunctional initiator through partial benzylation of the β-CD resulting in a CD-diol. Also, the ROP of D,L-LA catalyzed by 4-dimethylaminopyridine and initiated by all 21 OH groups of β-CD was employed by Xu et al. [15]. However, the above

Effect of the ortho-hydroxy group of salicylaldehyde in the A³ coupling reaction: A metal-catalyst-free synthesis of propargylamine

• Sujit Ghosh,
• Kinkar Biswas,
• Suchandra Bhattacharya,
• Pranab Ghosh and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 552–557, doi:10.3762/bjoc.13.53

• of natural products [1], potential therapeutic agents [2], oxotremorine analogues [3] and multifunctional amino derivatives [4][5]. Compounds like resagiline or selegiline (structures 1 and 2, Scheme 1) bearing a propargylamine moiety, are familiar as potent selective, irreversible monoamine oxidase

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• of new monomers and crosslinkers remained limited [4]. Mono-, di-, tri- and multifunctional (meth)acrylates are among the first choices for photopolymerized mixtures as they exhibit a favorable balance between reactivity and thermal stability upon storage [5][6][7]. Moreover, they comprise

3D printed fluidics with embedded analytic functionality for automated reaction optimisation

• Andrew J. Capel,
• Andrew Wright,
• Matthew J. Harding,
• George W. Weaver,
• Yuqi Li,
• Russell A. Harris,
• Steve Edmondson,
• Ruth D. Goodridge and
• Steven D. R. Christie

Beilstein J. Org. Chem. 2017, 13, 111–119, doi:10.3762/bjoc.13.14

• , to create multifunctional fluidic devices with embedded reaction monitoring capability. The selectively laser melted parts are the first published examples of multifunctional 3D printed metal fluidic devices. These devices allow high temperature and pressure chemistry to be performed in solvent

• of using 3D printing to produce microfluidic devices using AM techniques such as stereolithography (SL) [11], polymer jetting and fused deposition modelling (FDM) [12][13]. There is therefore considerable interest in the optimisation of chemical systems using this type of multifunctional continuous

• for inline reaction analysis due to its rapid data generation, however, it can often be difficult to interpret for complex multifunctional systems. On the other hand, chromatographic analysis methods produce much more concise spectra allowing quantitative data to be extrapolated, however, they often

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• by initially forming a dimer from multifunctional monomers, which then forms a trimer, then oligomer and finally a polymer (Figure 4) [24]. Kim and Hyun report the synthesis of polyurethane, discussing the associated numerical simulation they conducted to determine the dependency of shear rate on

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• reaction; γ-ketoallylphosphonate; organophosphorus chemistry; Introduction Phosphonates and their derivatives are an important class of substances that have a wide range of applications in numerous areas such as medicinal [1][2][3] and agricultural chemistry [4][5]. Among them, multifunctional derivatives

• yields and selectivity, using cyclic MBH acetates as starting materials, in the presence of DMAP or imidazole as additives (Scheme 2, reaction 6). Moreover, it has been demonstrated that the presence of a nitrogen atom and a phosphonate moiety in multifunctional compounds may improve their synthetic and

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

• reaction for the construction of acyclic acylhydrazino-peptomers. The consecutive multicomponent reactions produced a variety of acylhydrazino-peptomers in moderate to excellent yields (47–90%). These compounds are multifunctional intermediates that can be further functionalized to obtain new