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

• interest of synthetic and medicinal chemists. Synthesis of various propargylamines from various salicylaldehydes under metal-catalyst-free conditions. Representative examples of bioactive compounds bearing a propargylamine moiety and synthesis of various N-heterocycles from propargylamine-containing

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• the synthesis of kinamycin 9 derivatives, which exhibited a strong cytotoxic and anticancer activity (Scheme 4) [15]. Propionic acid derivatives are also useful substrates in syntheses of 1-indanones and isocoumarins [16]. These latter are essential reagents for the synthesis of bioactive compounds

Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

• Hisashi Masui,
• Sae Yosugi,
• Shinichiro Fuse and
• Takashi Takahashi

Beilstein J. Org. Chem. 2017, 13, 106–110, doi:10.3762/bjoc.13.13

• reproduce the same results anytime and anywhere using the same apparatus and reagents. As a result, synthetic chemists can spend more time on advanced and challenging problems. We previously reported automated syntheses of various bioactive compounds [5][6][7][8], including taxol, using our originally

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• compounds could be useful as potential novel lipid derivatives because of the presence of lipophilic chain and the phenolic amide conjugate. Results and Discussion Synthesis 10-Undecenoic acid was chosen as the lipid part as the derivatives of undecenoic acid have been reported to be potent bioactive

• compounds [12][13]. Additionally the terminal double bond of undecenoic acid provides a reactive group for further derivatization for producing potential functional derivatives. The synthetic route followed for the synthesis of the phenolipids is shown in Scheme 1. Initially, undecenoic acid was treated

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

• have been exploited as valuable building blocks in natural product syntheses, e.g., calyculins A and B as potent serine-threonine protein phosphatase inhibitors [6], as well as ligands in enantioselective reactions [7]. Furthermore, allylphosphonates are important bioactive compounds that exhibit

Selective and eco-friendly procedures for the synthesis of benzimidazole derivatives. The role of the Er(OTf)₃ catalyst in the reaction selectivity

• Natividad Herrera Cano,
• Jorge G. Uranga,
• Mónica Nardi,
• Antonio Procopio,
• Daniel A. Wunderlin and
• Ana N. Santiago

Beilstein J. Org. Chem. 2016, 12, 2410–2419, doi:10.3762/bjoc.12.235

• ), high selectivity and broad application. This method could help to produce bioactive compounds using an environmentally friendly procedure. ESP maps and charge density on carbonylic oxygen atoms for the studied aldehydes obtained at the BPW91/6-31+G* level. All maps used consistent surface potential

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

• Xiaofeng Zhang,
• Kenny Pham,
• Shuai Liu,
• Marc Legris,
• Alex Muthengi,
• Jerry P. Jasinski and
• Wei Zhang

Beilstein J. Org. Chem. 2016, 12, 2204–2210, doi:10.3762/bjoc.12.211

• new sequence initiated with a three-component [3 + 2] cycloaddition for preparing polycyclic scaffold 1 bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide rings. Those heterocyclic fragments could be found in bioactive compounds such as bromodomain, thrombin

• . Upon the completion of the reaction as monitored by LC–MS, the reaction mixture was concentrated and then isolated on a semi-preparative HPLC with a C18 column to afford purified product 1. Heterocyclic fragments in bioactive compounds. One-pot double [3 + 2] cycloadditions and denitrogenation for

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• diarylmethyl-substituted furans, which are otherwise hardly available molecules [39][40][41][42][43][44][45][46] and used for the synthesis of bioactive compounds [47]. Thus, the superelectrophilic activation of 5-HMF and 2,5-DFF could be of great value for organic synthesis. Results and Discussion The

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• a natural source: Coriandrone A isolated from the aerial parts of Coriandrum sativum [6] and other furo[3,2-h]isocoumarins have been reported as synthetic products [7][8][9]. In the last decade, our research group has been devoted to finding novel bioactive compounds from mangrove endophytic fungi

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• bioactive surfaces [8][14], imaging of biochemical processes [15], localization of bioactive compounds inside living cells [16], syntheses of small-molecule screening libraries [17], catenane and rotaxane syntheses [18], in reactions under continuous flow processing [19], polymer and surface science [20][21

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

• an important class of organophosphorus compounds that has attracted the attention of both industrial and medicinal chemists [5][6][7][8][9][10][11][12]. Many efforts have been made to prepare these bioactive compounds over the last 60 years [13]. There are two general approaches to the synthesis of

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

• offers the opportunity to find novel bioactive compounds with the potential to become drug leads. Regarding halotolerant myxobacteria, the 9 Mb genome of the Myxococcus fulvus strain HW-1 (ATCC BAA-855, suborder Cystobacterineae) was the first-of-its-kind to be sequenced [38]. Genome mining performed in

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• cellulolytic Sorangium strains harbor well-conserved homologs of both genes. Antibiotics from myxobacteria with a possible role in predation The following listing highlights few selected antibiotics from myxobacteria in the context of predation. For a comprehensive overview of bioactive compounds from

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• isolated from two solitary wasp species (Sceliphron caementarium and Chalybion californicum, Hymenoptera, Sphecidae) [100]. Based on a pre-screening of bacterial extracts, the detailed chemical analysis of selected strains revealed not only a broad range of known bioactive compounds, such as bafilomycins

Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

• Norbert Vida,
• Jiří Václavík and
• Petr Beier

Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12

• applications ranging from advanced materials to bioactive compounds [1][2][3]. One such fluorinated functional group which has become the focus of systematic investigation only recently is the pentafluorosulfanyl (SF5) group [4][5]. The combination of high stability [6], lipophilicity [7] and strong electron

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

• Yan Li,
• Xue Zhou,
• Guangfan Zheng and
• Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

• ; Findings Direct aminooxygenation of alkenes provides a straightforward and powerful approach to construct the 1,2-aminoalcohol skeleton [1], which is ubiquitous in bioactive compounds (such as the drugs bestatin (1) and tamiflu (2), the natural products Al-77-B (3) and hapolosin (4); Figure 1) [2] and has

• the cleavage of the N–O or C–N bond of the NHPI moiety. Further studies are underway in our lab. Bioactive compounds containing 1,2-aminoalcohol motif. The copper-catalyzed three-component aminooxygenation of styrenes with NFSI and NHPI derivatives. Reaction conditions: 1 (0.9 mmol, 3.0 equiv), NFSI

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

• hormones were among the first bioactive compounds whose aqueous solubilities were shown to be significantly enhanced via CD inclusion. For example, in an early study by Uekama et al. [14], the interactions between 18 steroid hormones and the native cyclodextrins α-, β- and γ-CD in aqueous solution were

Bifunctional phase-transfer catalysis in the asymmetric synthesis of biologically active isoindolinones

• Antonia Di Mola,
• Maximilian Tiffner,
• Francesco Scorzelli,
• Laura Palombi,
• Rosanna Filosa,
• Paolo De Caprariis,
• Mario Waser and
• Antonio Massa

Beilstein J. Org. Chem. 2015, 11, 2591–2599, doi:10.3762/bjoc.11.279

• of such a catalytic strategy to access the target compounds 1–4 in an efficient manner. The availability of efficient catalytic processes is a fundamental requirement for the development of scalable synthetic routes of bioactive compounds. Thus, in the present work, we firstly reconsidered this

• to obtain both the enantiomers of chiral bioactive compounds. In this case, we focused on (R,R)-8a, which afforded the required (S)-7 (the absolute configuration has been previously determined by vibrational circular dichroism) [31]. Asymmetric synthesis of 9 by decarboxylation of (S)-7 Although

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

• Marcel Mirel Popa,
• Emilian Georgescu,
• Mino R. Caira,
• Florentina Georgescu,
• Constantin Draghici,
• Raluca Stan,
• Calin Deleanu and
• Florea Dumitrascu

Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121

• structural motifs for a broad range of compounds with applications as advanced fluorescent materials [2][3], ligands [4][5], bioactive compounds [6], and for the design of dynamic chemical devices [7][8][9][10]. The most accessible route to hybrid heteroarenes is the direct coupling [1][11][12]. However, in

• indolizines and azaindolizines are known as fluorescent materials [2][3][4][15] with applications as chemosensors [16] and as bioactive compounds [17][18][19][20]. For example, starting from bispyridyl derivatives such as 1 and 3, fluorescent compounds from the class of indolizines, as for example compounds 2

Novel carbocationic rearrangements of 1-styrylpropargyl alcohols

• Christine Basmadjian,
• Fan Zhang and
• Laurent Désaubry

Beilstein J. Org. Chem. 2015, 11, 1017–1022, doi:10.3762/bjoc.11.114

• impossible to achieve [4][8][9]. The importance of cyclopentenones as intermediates to the synthesis of bioactive compounds prompted us to explore the synthetic potential of this novel rearrangement of 1-styrylpropargyl alcohols (Table 1). Toward this purpose, a number of other substrates were synthesized

Thiazole formation through a modified Gewald reaction

• Carl J. Mallia,
• Lukas Englert,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 875–883, doi:10.3762/bjoc.11.98

• substitution of the α-carbon to the cyano group. Keywords: design of experiment (DOE); 1,4-dithiane-2,5-diol; Gewald reaction; thiazole; thiophene; Introduction Thiazoles are privileged motifs which are encountered in many naturally occurring bioactive compounds and pharmaceuticals with indications in a

Ruthenium-catalyzed C–H activation of thioxanthones

• Danny Wagner and
• Stefan Bräse

Beilstein J. Org. Chem. 2015, 11, 431–436, doi:10.3762/bjoc.11.49

• . Keywords: C–H activation; metal catalysis; thioxanthones; Introduction Thioxanthones (Figure 1) belong as a unique member to the large group of benzoannelated heterocycles [1]. They have found extensive use in biomedical applications (drugs and other bioactive compounds [2][3][4][5]) and material sciences

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

• Pavel K. Mykhailiuk

Beilstein J. Org. Chem. 2015, 11, 16–24, doi:10.3762/bjoc.11.3

• trifluoromethylated derivatives play a major role in chemistry [28], their more lipophilic analogues – C2F5 [1][29][30] and SF5 [1][31] – only gain popularity. The C2F5-substituted derivatives, for example, often have higher activity compared with the CF3-counterparts [32][33]. Therefore, some bioactive compounds

• alkynes 1–12 with C2F5CHN2 gives 3,5-disubstituted ones. Also, alkaline hydrolysis of the ester group in 1a gave acid 25 – potential building blocks for medicinal chemistry and drug discovery: many bioactive compounds, including the insecticidal agent DP-23, contain the residue of the CF3-analogue of 25

• layer was separated. The aqueous layer was washed with CH2Cl2 (2 × 3 mL). The combined organic layers were dried over Na2SO4 and evaporated under vacuum to provide the pure product. Bioactive compounds and agrochemicals with fluorinated pyrazoles. Bioactive compounds with C2F5 group [34][35][36]. X-ray

A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives

• Debabrata Samanta,
• Anup Rana,
• Jan W. Bats and
• Michael Schmittel

Beilstein J. Org. Chem. 2014, 10, 2989–2996, doi:10.3762/bjoc.10.317

• bioactive compounds. For instance, thiadiazole containing heterocycles are known to exhibit important anti-inflammatory, antihypertensive, anti-HIV and antituberculosis activity [1]. Within this family, 1,2,4-thiadiazoles display notable medicinal properties as potent neuroprotectors [2

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• of a variety of polycyclic structures containing typical structural elements of bioactive compounds [82]. Since 73 provides manifold possibilities for structural modifications, the generation of complex and structurally diverse scaffolds could be achieved in very few steps (diversity-oriented