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

• phenylalkynes 187 and aldehydes 188 to trans-2,3-disubstituted 1-indanones 189 in the one-pot reaction (Scheme 53) [82]. A synthesis of 3-aryl-1-indanone derivatives 192 from aromatic aldehydes 190 and alkyne derivatives 191 has been patented by Xi and Liu in 2016 [83]. The reaction proceeded in the presence of

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

• Michaela Prothiwa,
• Dávid Szamosvári,
• Sandra Glasmacher and
• Thomas Böttcher

Beilstein J. Org. Chem. 2016, 12, 2784–2792, doi:10.3762/bjoc.12.277

• one-pot reaction for the synthesis of 2-heptyl-chromen-4-one (1-O-HHQ, 4) which includes esterification, Baker–Venkataraman rearrangement and subsequent acid-catalyzed ring closure to affort the 1-O-HHQ in 60% yield [36] (Scheme 1). The 2-heptyl-3-hydroxychromen-4-one (1-O-PQS, 13) was previously

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• Dracocephalum rupestre, have been synthesized in a one-pot reaction. The separation of 2a–d and 3a–d was achieved by preparative HPLC. The four stereoisomers of each natural product were separated by analytical chiral HPLC and their absolute configuration was studied by the combination of HPLC–ECD measurements

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

• environmentally friendly synthetic method, to obtain different derivatives containing the benzimidazole core by a one-pot reaction. Additionally, Er(OTf)3 was selected as the catalyst to achieve the selective formation of products in order to avoid tedious work-up and product separation procedures. Moreover

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

• Arne Klinkebiel,
• Ole Beyer,
• Barbara Malawko and
• Ulrich Lüning

Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219

• cleaved in a one-pot reaction. The tetrafold cleavage yielded hydroxytriazine 17e in 52% yield. All tricarboxylic acids 17 are considerably less soluble in most solvents when compared to the respective methyl esters 16. Nevertheless, they are sufficiently soluble in, for instance, DMSO or in base to allow

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

• addition to formaldehyde, other aldehydes could also be used for the [5 + 1] annulation according to literature [34][35]. Conclusion A one-pot reaction sequence involving [3 + 2] cycloaddition of azomethine ylides, [3 + 2] cycloaddition of azides with alkenes, and denitrogenation followed by a [5 + 1

Application of heterocyclic aldehydes as components in Ugi–Smiles couplings

• Katelynn M. Mason,
• Michael S. Meyers,
• Abbie M. Fox and
• Sarah B. Luesse

Beilstein J. Org. Chem. 2016, 12, 2032–2037, doi:10.3762/bjoc.12.191

• Diels–Alder (US-IMDA) reaction with substituted 2-furaldehyde and allylamine (Scheme 1), which provides direct access to N-arylepoxyisoindolines 1 through a simple, one-pot reaction [23]. Through this stereoselective tandem process, six new bonds and four stereocenters are generated in one synthetic

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• using Zn(OAc)2 to a 2-step, one pot reaction with sodium hydride in tetrahydrofuran, followed by the addition of zinc(II) chloride. Zinc(II) and BF2+ chelates were purified by silica gel column chromatography to isolate the chelates as blue solids and the identity and purity was confirmed by NMR

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• publication, Gade et al. also achieved a high selectivity toward GD in a one-pot reaction starting from glycerol and DMC [66]. Using tetramethylammonium hydroxide ([TMA][OH]) as basic catalyst, a high selectivity (78%) for GD was reached under mild operating conditions (80 °C, 90 min). The results suggested

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• that is produced in Streptomyces species [134][135]. The respective biosynthetic pathway has been fully reconstituted in an in vitro one-pot reaction [136]. The flavoprotein EncM transforms the C12 methylene group of the octaketidic PKS type II product 139 in a two-step oxidation sequence using the

One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

• Bo Yang,
• Chuanye Tao,
• Taofeng Shao,
• Jianxian Gong and
• Chao Che

Beilstein J. Org. Chem. 2016, 12, 1487–1492, doi:10.3762/bjoc.12.145

• reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group. Keywords: Groebke–Blackburn–Bienaymé reaction; imidazo[1,2-a]pyridines; multi-component reaction; one-pot reaction; Introduction

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

• were resistant to this reaction. The trimethylchlorosilane-mediated one-pot reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate (8) with aryl aldehydes 9 and urea under Biginelli conditions has been presented by Timoshenko et al. (Scheme 3) [27]. The resulting 4-hydroxytetrahydropyrimidin-2

• -aminophosphonate 26 in 99% yield (Scheme 7) [34]. The reaction of isatin (27) with diethyl phosphite and benzylamine under similar conditions gave the corresponding α-aminophosphonate 28 in 90% yield together with small amounts of α-hydroxyphosphonate 29 as a side product (Scheme 8). The one-pot reaction of

• for the rapid access of heterocyclic phosphonates is the combination of the Kabachnik–Fields reaction with a subsequent ring closure. Thus, the one-pot reaction of 5-chloro-2-pentanone (46) with ammonia and diethyl phosphonate in ethanol lead to the non-isolable intermediate 47 which was directly

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• unsymmetrically substituted diarylpyridines, difficult to access by other methods. Keywords: arylpyridines; cross coupling reaction; heteroaromatics; one-pot reaction; palladium catalyst; Introduction Nitrogen heterocycles are an important class of compounds widely present in agrochemical products [1][2] and

• monoarylated intermediate. Two alternative approaches were based on a one-pot reaction concept, which is advantageous from the point of view of costs (solvents, adsorbents etc.) and work-up procedure. Route 2 is based on the stepwise diarylation of 1 without isolation of the monoarylated product. We also

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

• Guozheng Huang,
• Simon Schramm,
• Jörg Heilmann,
• David Biedermann,
• Vladimír Křen and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

• , Prague 4, CZ-14220, Czech Republic 10.3762/bjoc.12.66 Abstract Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding

• pure (10R,11R)- and (10S,11S)-hydnocarpin D described to date and gives 56% yield starting from commercially available silibinin in a one-pot reaction. Evaluation of Mitsunobu conditions and reagents applied for esterification and dehydration, respectively, enabled us to exclusively obtain either the

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

• Mamoru Tobisu,
• Takuya Igarashi and
• Naoto Chatani

Beilstein J. Org. Chem. 2016, 12, 654–661, doi:10.3762/bjoc.12.65

• derivatives by treatment with protecting groups in a one-pot reaction sequence. The reactivity of 1g has previously been well-exploited in catalytic borylation of aryl halides [22][23][24][25][26][27]. Herein, we report the C–H borylation of arenes using 1g catalyzed by an Ir/N-heterocyclic carbene (NHC

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

• Rajeev S. Menon,
• Akkattu T. Biju and
• Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

• catalyst rapidly shuttles the intermediate δ-keto aldehyde 61 to the final product preventing the erosion of enantioselectivity [54]. This cascade reaction constitutes a fine example of symbiotic dual-catalysis wherein both catalysts perform better together in a one-pot reaction than they do independently

• product 81 (Scheme 45). The yields are moderate; however excellent diastereo- and enantioselectivities were observed for the one-pot reaction [62]. In a similar fashion, an asymmetric multicatalytic cascade reaction involving the dienal 82 and unsaturated cyclic sulfonylimine 83 afforded spiro-fused

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• experimental data). The compounds myo-11 and scyllo-11 were obtained in 80% and 76% yield, respectively in a one pot reaction by the treatment of myo-1 and scyllo-1 with triphenylmethyl chloride in pyridine and a catalytic amount of DMAP at 40 °C for three days followed by the addition of acetic anhydride [46

• chloride, followed by peracetylation with acetic anhydride in a one pot reaction [46]. Myo-18 and scyllo-18 were obtained in 74 and 70% yield, respectively. It is worthy to note that the tertiary hydroxy group in myo-18 and scyllo-18 remained unprotected under these conditions. The literature data are

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• that compound 44 showed the highest activity against B. subtilis and E. coli due to the presence of a rigid pyridine nucleus. The authors further prepared various amide-linked bistriazoles by a three-component one-pot reaction of the amide-linked dialkynes, benzyl bromides and sodium azide catalyzed by

• 1,2,3-bistriazole. The synthesis of bistriazoles via a sequential one-pot reaction. Previous reports on the copper-catalyzed Huisgen cycloaddition to bistriazoles with spacers. Previous reports on the copper-catalyzed Huisgen cycloaddition to bistriazoles with spacers. Acknowledgements This project

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

• Enas M. Malik,
• Younis Baqi and
• Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

• inert solvent (e.g., nitrobenzene) to form 1-aminoanthraquinone-2-sulfonic acid (4), the salt of which is then brominated to give bromaminic acid sodium salt (2). Sulfonation of 3 (oleum method) is achieved by the use of oleum followed by bromination in a one-pot reaction. Therefore, the oleum method is

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• accomplished in a one-pot reaction under Wolff–Kishner reaction conditions to generate 223 and 259, respectively (Scheme 41). Cycloaddition reactions [2 + 2] Cycloaddition: Roemer and Lentz [175] have reported the synthesis of fluorinated ferrocenophanes from 1,10-bis(trifluorovinyl)ferrocene and 1,4-(1,10

Azobenzene-based inhibitors of human carbonic anhydrase II

• Leander Simon Runtsch,
• David Michael Barber,
• Peter Mayer,
• Michael Groll,
• Dirk Trauner and
• Johannes Broichhagen

Beilstein J. Org. Chem. 2015, 11, 1129–1135, doi:10.3762/bjoc.11.127

• -pot reaction over three steps in 25%. By diazotization of 1d and trapping the salt with TMS-azide, we obtained azido azobenzene 1e in 63% yield through a [3 + 2] and retro-[3 + 2] cycloaddition (Scheme 1b) according to the procedure of Barral et al [10]. For the Mills reaction, different nitroso

• led to azobenzenes 1a [6], 1b [9] and 1c, in moderate to low yields (43%, 38% and 25%, respectively) (Scheme 1a). Employing methylene-protected aniline 2 (crystal structure depicted in Scheme 1e) according to the procedure from Supuran and co-workers [6], amino azobenzene 1d was isolated after a one

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

• Hongnan Sun,
• Binbin Huang,
• Run Lin,
• Chao Yang and
• Wujiong Xia

Beilstein J. Org. Chem. 2015, 11, 524–529, doi:10.3762/bjoc.11.59

• (R)-2-phenyl-N-tosylazetidine (1o) with 2-bromoethanol and/or 3-bromopropanol under the one-pot reaction conditions, afforded the seven-membered product (S)-3o and the eight-membered compound (S)-3ob in 65% and 60% yield with 52% and 67% ee, respectively. Based on the above results, a viable

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• [146]. The coupling reaction with N-hydroxyphthalimide (154b) was carried out using the NaI/aqueous t-BuOOH/KOH system instead of Bu4NI/t-BuOOH in decane [146]. The resulting activated esters 159 and 160 were isolated or used in the one-pot reaction with amines to prepare amides (Scheme 32). The

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

• Bianca Rossi,
• Nadia Pastori,
• Simona Prosperini and
• Carlo Punta

Beilstein J. Org. Chem. 2015, 11, 66–73, doi:10.3762/bjoc.11.10

• reported optimized conditions for the selective free radical nucleophilic addition of ethers and alcohols to ketimines generated in situ under non-anhydrous conditions. The protocol consists of a three-component, one-pot reaction involving an aromatic amine, a ketone, and the source of the ketyl radical

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

• Pavel K. Mykhailiuk Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine; and Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine 10.3762/bjoc.11.3 Abstract A one-pot reaction between C2F5CH2NH2·HCl, NaNO2 and electron