Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al₂O₃/MeSO₃H

• Hashem Sharghi,
• Mahdi Aberi,
• Mohsen Khataminejad and
• Pezhman Shiri

Beilstein J. Org. Chem. 2017, 13, 1977–1981, doi:10.3762/bjoc.13.193

• recycled catalyst could be reused five times without any significant loss in activity (Figure 1). Conclusion In conclusion, Al2O3 and MeSO3H exhibited an excellent reactivity in the one-pot synthesis of 3-arylquinolines using anilines and styrene oxide. The methodology has the advantages of good to

• . AMA = Al2O3/methanesulfonic acid Optimization studies for the synthesis of 6,7-dimethyl-3-phenylquinoline (3a) from 3,4-dimethylaniline (1a, 1.0 mmol) with styrene oxide (2, 2.0 mmol) in open air. One-pot synthesis of 3-arylquinolines from the reaction of different anilines (1.0 mmol) with styrene

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

• Joseph L. Howard,
• William Nicholson,
• Yerbol Sagatov and
• Duncan L. Browne

Beilstein J. Org. Chem. 2017, 13, 1950–1956, doi:10.3762/bjoc.13.189

• physical form in the one-pot two-step mechanochemical procedure. Optimised conditions for the one-pot synthesis. Substrate scope of the one-pot, 2 step mechanochemical synthesis (isolated yields). a1 equiv Selectfluor used. Optimisation of pyrazolone formation. Optimisation of pyrazolone fluorination

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

• predominantly towards di-fluorinated product [102]. Multi-component reactions Multi-component reactions are one of the most powerful tools for the one pot synthesis of complex molecular structures with various functional groups [103][104][105][106][107][108]. Starting from the development of the Strecker

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

• Grzegorz Mlostoń,
• Paulina Pipiak,
• Róża Hamera-Fałdyga and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

• ]. General Procedure for the one-pot synthesis of ethenes 9a–f: A hetaryl thioketone 1 (1 mmol) was dissolved in THF (2–3 mL) and the solution was cooled to 0 °C (ice bath). Then, the mixture was treated with small portions of an ethereal solution of TMS-CHN2 (2 M, 0.5 mL, 1 mmol). The reaction was complete

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• -mediated oxidative dehydrogenation. NBS-mediated oxidative dehydrogenation of tetrahydro-β-carbolines. One-pot synthesis of various methyl(hetero)arenes from o-aminobenzamide in presence of di-tert-butyl peroxide (DTBP). Oxidative dehydrogenation of 1, 4-DHPs. Synthesis of quinazolines in the presence of

• lithium carbonate at high temperature. 4-Methoxy-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted benzazoles. Plausible mechanism of the 4-methoxy-TEMPO-catalyzed transformation. One-pot synthesis of 2-arylquinazolines, catalyzed by 4-hydroxy-TEMPO. Oxidative dehydrogenation – a key step in

• -pot synthesis of substituted dihydroquinazolines 35 from a variety of o-aminobenzylamines with appropriate aldehydes and alkylnitrates. The initial condensation of substituted o-aminobenzylamines with aldehydes afforded the substituted tetrahydroquinazoline 34, which was subsequently treated with a

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• , entries 3, 9 and Table 3, entries 2, 13 and 19). Therefore, this method is suitable for the synthesis of numerous oxazoles with diverse functionalities. Our strategy for the concise synthesis of 2,4,5-trisubstituted oxazoles. Synthesis of DMPOPOP. One-pot synthesis of 5-(triazinyloxy)oxazole under

• altered. However, these reactions require strongly acidic conditions or high temperatures. Therefore, a mild method for the synthesis of diverse trisubstituted oxazoles using three commercially available compounds with a wide variety of structures is still desired. Previously, we reported a one-pot

• synthesis of oxazolone from carboxylic acids and amino acids using a dehydrative condensing reagent, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM [19][20][21][22])[23]. Formation of 5-(triazinyloxy)oxazole is also reported to occur when an excess of DMT-MM was used. Recently

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

• Jessica Hilschmann,
• Gerhard Wenz and
• Gergely Kali

Beilstein J. Org. Chem. 2017, 13, 1310–1315, doi:10.3762/bjoc.13.127

• length as well as statistical distribution of stopper groups along the axis. Herein, we report for the first time a simple one-pot synthesis of polyrotaxanes with control of length and sequence of the polymer axis through RAFT rotaxa-polymerization of isoprene in water. RAFT polymerization was indeed

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• and so on [5][6]. The multistep synthesis may or may not involve inline separation units and also in-line analytical tools to monitor the process. The multistep synthesis where the intermediate separation or work-up is not required is conventionally termed as ‘one pot’ synthesis, which is also called

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• (Table 5). Proposed mechanism In order to assess the mechanism of the three-step one-pot synthesis of 5, the reaction between the commercial reagents 6a and 0.5 equiv of diphenyl diselenide (as analogue to the dialkyl diselenides 8 proposed as intermediates) was carried out in the presence of 1 equiv t

• oxygen atmosphere. The method is also applicable to the synthesis of functionalized heterocycles in good to excellent yields. One-pot synthesis of vinyl and alkynyl selenides. Effect of t-BuOK on the formation of n-octyl alkynyl selenide 5a. Effect of reactants concentration on alkynyl selenide formation

• . Synthesis of N-ethyl-2-(n-octylselanyl)-1H-indole (9) and 3-iodo-2-(n-octylselanyl)benzofuran (10). Control reactions and mechanistic study. Proposed mechanism for the formation of selenides 5. Proposed mechanism for the formation of indole 9. Solvent screening for the one-pot synthesis of selenide 5a.a

N-Propargylamines: versatile building blocks in the construction of thiazole cores

• S. Arshadi,
• E. Vessally,
• L. Edjlali,
• R. Hosseinzadeh-Khanmiri and
• E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

• thiazole-2-thiones 3 through the thermal cyclocondensation of N-propargylamines 1 with carbon disulfide as developed by Batty and Weedon [75]. (a) One-pot synthesis of 2-benzylthiazolo[3,2-a]benzimidazoles 6 through a base-catalyzed cascade reaction of internal N-propargylamines 4 and CS2. (b) Synthesis of

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

• synthesis of the [14C]indene 176, which was next applied for the examination of the indene bioconversion network expressed in Rhodococcus sp. KY1 [79]. The [14C]1-indanone 175 was obtained in the one-pot synthesis involving the Friedel–Crafts acylation of [14C]benzene 173 with chloropropionic acid chloride

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

• Mikael Bols and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12

• with this, the analogue of 46 having a TIPDS group rather than a DTBS was not particularly unreactive, as it is more flexible due to the bigger ring. The Yang group used 46 in a one-pot synthesis of a trisaccharide, where they took advantage of 46 being less reactive than partially benzoylated

Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions

• Andreas C. Boukis,
• Baptiste Monney and
• Michael A. R. Meier

Beilstein J. Org. Chem. 2017, 13, 54–62, doi:10.3762/bjoc.13.7

• indicate the formation of the respective Biginelli–Passerini product. As a proof of principle, the Biginelli and Passerini reaction were combined in a one-pot synthesis. In this experiment, the Biginelli reaction was performed with an excess of the aldehyde component (three equivalents) in a minimal amount

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

• Manjunatha Narayanarao,
• Lokesh Koodlur,
• Vijayakumar G. Revanasiddappa,
• Subramanya Gopal and
• Susmita Kamila

Beilstein J. Org. Chem. 2016, 12, 2893–2897, doi:10.3762/bjoc.12.288

• of biological importance [1][2]. The regio- and stereoselective construction of spiro compounds by utilizing the 1,3-dipolar cycloaddition reaction of azomethine ylides has been reported [3][4][5][6]. However, unlike the previous reports, the present method is concise and facilitates the one-pot

• synthesis of multifunctionalized spiranes. The earlier works reveal the use of different reaction conditions to prepare functionalized spiroindane, spiropyrolidine, spiropyrrolizidine and spirooxindole derivatives. Among them, the 1,3-dipolar cycloaddition based route is preferred due to multiple advantages

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations

• Serena Traboni,
• Emiliano Bedini and
• Alfonso Iadonisi

Beilstein J. Org. Chem. 2016, 12, 2748–2756, doi:10.3762/bjoc.12.271

• experimentally simple tool for the straightforward access to saccharide building-blocks useful in organic synthesis. Keywords: carbohydrates; one-pot synthesis; regioselective protection; silyl protecting group; solvent-free reaction; Introduction The application of an orthogonal set of protecting groups

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

• measured, but these compounds, along with naringenin were virtually inactive in the DPPH radical scavenging test (IC50 > 200 µg/mL), compared to the positive control quercetin (IC50 = 9.4 ± 0.6 µg/mL). Conclusion An efficient one pot synthesis of dracocephins A (2a–d) and B (3a–d) was achieved starting

Et₃B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita–Baylis–Hillman alcohols

• Ahlem Abidi,
• Yosra Oueslati and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2402–2409, doi:10.3762/bjoc.12.234

• interesting synthesis of bicyclic dienones in a one-pot process involving the reaction of 2-(acetoxymethyl)cyclohex-2-enone with 1,3-dicarbonyl compounds using K2CO3 as a weak base. Later, Chamakh and Amri [38] have described a one-pot synthesis of (E)-4-alkylidene-2-cyclohexen-1-ones through a cross coupling

β-Amino functionalization of cinnamic Weinreb amides in ionic liquid

• Yi-Ning Wang,
• Guo-Xiang Sun and
• Gang Qi

Beilstein J. Org. Chem. 2016, 12, 2372–2377, doi:10.3762/bjoc.12.231

• liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf2]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, the presented process can be readily performed as a one-pot synthesis at room temperature. Moreover, the preparation has the

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

• 365 nm. Low resolution mass spectra were recorded with APCI (atmospheric pressure chemical ionization). The final products were purified on Angela HP-100 pre-LC system with a Venusil PrepG C18 column (10 μm, 120 Å, 21.2 mm × 250 mm). General procedure for the one-pot synthesis of compounds 7 The

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

• Roman Yu. Peshkov,
• Elena V. Panteleeva,
• Wang Chunyan,
• Evgeny V. Tretyakov and
• Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

• Discussion The suggested one-pot synthesis of alkylcyanobiaryls 5 comprises consecutive generation of terephthalonitrile dianion (12–) [30][31][32] by the addition of metallic sodium to a suspension of dinitrile 1 in liquid ammonia, treating of the thus formed 12− salt with a twofold excess of nitrile 2

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

• selective CDK2 inhibition properties [34][35]. As a continuing effort, we report herein our recent efforts in the development of a GBB-based MCR method for the one-pot synthesis of diverse quinazolin-2-one fused imidazo[1,2-a]pyridines (Scheme 1). Parts of the work have been disclosed in a previous patent

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

• Daniela Obels,
• Melanie Lievenbrück and
• Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 1395–1400, doi:10.3762/bjoc.12.133

• -dibromooctane can easily be conducted through a one-pot synthesis. Swellable networks can be obtained by radical copolymerization of 2a with N-VP. Furthermore, the conversion of the double bonds through thiol–ene click reaction with 2-aminoethanethiol hydrochloride leads to paraffinic oligomers 4 bearing

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

• conditions are summarized in Table 1. 3.2 Domino Knoevenagel/hetero-Diels–Alder process The one-pot synthesis of dihydropyrans via a three-component reaction between an activated methylene compound, an aldehyde and an electron-rich alkene was firstly reported by Tietze et al. [72]. Collignon et al. applied

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

• Gastón Silveira-Dorta,
• Sergio J. Álvarez-Méndez,
• Víctor S. Martín and
• José M. Padrón

Beilstein J. Org. Chem. 2016, 12, 957–962, doi:10.3762/bjoc.12.94

• mixture. In the one-pot synthesis of anti-β-amino alcohols, the best results were achieved when the reactions were run in Et2O [16]. A fine tuning of the reducing agent was also necessary to obtain the desired products. Our first goal was to study the outcome of the reaction in terms of solvent and the