Metal-free formal synthesis of phenoxazine

• Gabriella Kervefors,
• Antonia Becker,
• Chandan Dey and
• Berit Olofsson

Beilstein J. Org. Chem. 2018, 14, 1491–1497, doi:10.3762/bjoc.14.126

• pot-synthesis of 2. aBased on recovered 3. Formal synthesis of phenoxazine (1). aBased on recovered 3. Optimization of the O-arylation of route A.a Supporting Information Supporting Information File 181: Experimental details for the synthesis of starting materials and products, analytical data for

• converted to product upon longer reaction time. Compounds containing a phenoxazine moiety. Reported syntheses of phenoxazine derivatives. Retrosynthesis of phenoxazine. Synthesis of iodonium salt 5a. Synthesis of iodonium salt 7. O-Arylation via route B. a) Cyclization of diaryl ether 3. b) Attempted one

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

• Jiyun Sun,
• Xiaohua Zhen,
• Huaibin Ge,
• Guangtao Zhang,
• Xuechan An and
• Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

• . Study on the presumed Togni reagent 1-mediated trifluoromethylation followed by PhIO-mediated azirination. Togni reagent/PhIO-mediated one-pot synthesis of β-trifluoromethyl 2H-azirines. Reaction conditions: 1 (1.2 mmol), 5 (1.0 mmol), CuI (0.2 mmol), PhIO (1.5 mmol) in DCE (10 mL) unless otherwise

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

• Mark Kelada,
• John M. D. Walsh,
• Robert W. Devine,
• Patrick McArdle and
• John C. Stephens

Beilstein J. Org. Chem. 2018, 14, 1222–1228, doi:10.3762/bjoc.14.104

• the development of novel biologically active compounds based on the pyrazolopyrimidinone scaffold, we sought to develop a simple one-pot synthesis of the nitrogen-fused bicyclic system. In order to establish reaction conditions for this one-pot synthesis, we began by seeking general reaction

• conditions for the microwave-assisted generation of the intermediate 5-aminopyrazoles. Once established, this methodology could be expanded to generate a one-pot synthesis of pyrazolo[1,5-a]pyrimidinones. Typical methods for preparing 5-aminopyrazoles require conventional heating of the appropriate β

• convenient and general microwave-assisted method for the synthesis of the 5-aminopyrazoles in hand, we next focused our attention on its application to the one-pot synthesis of pyrazolo[1,5-a]pyrimidinones. The synthesis of pyrazolo[1,5-a]pyrimidinone 3a was chosen as the model reaction (Scheme 2). Initial

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

• Aritra Chaudhury,
• Mana Mohan Mukherjee and
• Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

• turned our attention to devise a one-pot protocol to achieve the same derivative. The one-pot synthesis of this target is particularly challenging because of the presence of the two 1,2-cis glycosidic linkages which are likely to make product isolation particularly difficult at the end of the

• orthogonal strategy for a one-pot synthesis of the targeted tetrasaccharide (Scheme 5). The disaccharide acceptor 4 was glycosylated with galactosyl trichloroacetimidate donor 2 at −15 °C using 30 mol % of TMSOTf. After full consumption of the starting materials (TLC), into the same pot the second acceptor 7

• linkages could be prepared with a yield and a selectivity which were high enough to allow the one-pot synthesis. The tetrasaccharides associated with the pneumonicoccal serogroup 6. Retrosynthetic analysis. Preparation of D-glucosyl donor 6. Reaction conditions: a) NapBr/PMBCl, NaH, DMF, rt, 12 h, 90% (6a

Imide arylation with aryl(TMP)iodonium tosylates

• Souradeep Basu,
• Alexander H. Sandtorv and
• David R. Stuart

Beilstein J. Org. Chem. 2018, 14, 1034–1038, doi:10.3762/bjoc.14.90

• as an important scaffold. Scope of compatible aryl groups. Conditions: 1 (0.5 mmol, 1 equiv), potassium phthalimide (2.5 mmol, 5 equiv), toluene (2.5 mL), 100 °C, 24 hours. Isolated yields are reported. One-pot synthesis of anilines. Discovery and optimization of reaction conditions.a Comparison of

An efficient and facile access to highly functionalized pyrrole derivatives

• Meng Gao,
• Wenting Zhao,
• Hongyi Zhao,
• Ziyun Lin,
• Dongfeng Zhang and
• Haihong Huang

Beilstein J. Org. Chem. 2018, 14, 884–890, doi:10.3762/bjoc.14.75

• Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, China 10.3762/bjoc.14.75 Abstract A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily

• substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research. Keywords: azomethine ylides; 1,3-dipolar cycloaddition; one-pot synthesis; polysubstituted pyrroles; pyrrolo[3,4-c]pyrrole-1,3-diones

• -1,3-diones [8][9][10] via 1,3-dipolar cycloaddition without any chiral catalysts/ligands and a facile access to highly substituted pyrroles with amide groups or ester groups. Herein, we propose a straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar

Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence

• Amarendar Reddy Maddirala and
• Peter R. Andreana

Beilstein J. Org. Chem. 2018, 14, 875–883, doi:10.3762/bjoc.14.74

• spirocyclic 2-oxindoles. Post-Ugi-4CR/transamidation/cyclization sequence. Base-promoted intramolecular 5-endo-dig cyclization. Reaction scope with varying combinations of substrates. Synthesis of 5-chloro-1'-phenylspiro[indoline-3,2'-pyrrolidine]-2,5'-dione (8a). Method applicability for the one-pot

• synthesis of 5-HT6 receptor antagonist 8j [53]. Optimization conditions for the intramolecular cyclization (Scheme 3, 6→7a and 7a').a Supporting Information Supporting Information File 50: 1H and 13C NMR spectroscopic data for compounds 7a–k and 8a–j, and X-ray crystal structure details for 7a

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

• Natalia Soldatova,
• Pavel Postnikov,
• Olga Kukurina,
• Viktor V. Zhdankin,
• Akira Yoshimura,
• Thomas Wirth and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 849–855, doi:10.3762/bjoc.14.70

• sulfuric acid has been developed. The procedure allows the synthesis of a wide range of iodonium salts containing electron-donating and electron-withdrawing substituents. Particularly attractive is the possibility of the one-pot synthesis of symmetric bis-aryliodonium salts directly from arenes via an

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• 7a. ‘One-pot’ synthesis of diketopiperazine-fused triazolobenzodiazepines 7a and 7b. Synthesis of hydantoin-fused triazolobenzodiazepine 10. Reaction conditions: 1. 2-azidobenzaldehyde 1 (1.85 mmol), propargylamine (2a, 1.85 mmol), trichloroacetic acid (9, 1.85 mmol), benzyl isocyanide 4 (1.85 mmol

Mannich base-connected syntheses mediated by ortho-quinone methides

• Petra Barta,
• Ferenc Fülöp and
• István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

• reactions is definitely more advantageous. Ionic liquids have also attracted considerable attention due to their „green chemistry” values, including reusability, high thermal stability and non-inflammability. Hajipour et al. reported the one-pot synthesis of 1-amidoalkyl-2-naphthols catalysed by N-(4

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na₂S₂O₈

• Teppei Sasaki,
• Katsuhiko Moriyama and
• Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

• -bromocoumarins, the C–Br bond of 3-bromo-4-phenylcoumarin was smoothly converted into 4-phenylcoumarins bearing C–H, C–S, C–N, and C–C bonds at 3-position. We believe the present method will be useful for the preparation of various 4-arylcoumarin derivatives due to its simple one-pot synthesis. ORTEP of 3-bromo

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

• Masanori Inaba,
• Tatsuya Sakai,
• Shun Shinada,
• Tsuyuka Sugiishi,
• Yuta Nishina,
• Norio Shibata and
• Hideki Amii

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

• 1a. Other examples of the one-pot synthesis of fluorinated phthalides 1 are given in Scheme 3. The reactions of 2-cyanobenzaldehyde (2) with organosilicon compounds (RF–SiMe3) proceeded cleanly by the use of KF (conditions A) or Et3N (conditions B). As a consequence, pentafluoroethyl

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides

• Irwan Iskandar Roslan,
• Kian-Hong Ng,
• Gaik-Khuan Chuah and
• Stephan Jaenicke

Beilstein J. Org. Chem. 2017, 13, 2739–2750, doi:10.3762/bjoc.13.270

• -efficient protocols, we have employed transition-metal-free approaches for the one-pot synthesis of imidazo[1,2-a]pyridines and thiazolamines by coupling β-ketoesters or their derivatives, phenylacetones and phenylacetophenones, with aminopyridines [20][21] and thioureas [22]. The strategy involves in situ

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

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

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

• ) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• one-pot process. Here, we report the development of the one-pot synthesis of these title compounds by a consecutive pseudo three-component approach and the investigation of the luminescence behavior by absorption and emission spectroscopy. Results and Discussion Synthesis and structure of 4

• and non-conjugated bichromophores in a rapid fashion. Studies directed towards the one-pot synthesis of more complex polycyclic emitters are currently underway. The ORTEP-style plot of crystal structure 4b (ellipsoids are draw at the 40% probability level). The ORTEP-type plot of the crystal structure

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• ); HRMS (ESI) m/z [M + Na]+: calcd. for C23H18N2OF2Na, 399.12794; found, 399.1279 (0 ppm); m/z [M + H]+: calcd. for C23H19N2OF2, 377.14599; found, 377.1454 (2 ppm); m/z [M – HF + Na]+: calcd. for C23H17N2OFNa, 379.12171; found, 379.1216 (0 ppm). One pot synthesis of (2-(1,1-difluoro-3-phenylpropyl)imidazo

• 7e by X-ray crystallography analysis. Retrosynthetic scheme for the preparation of our target molecules A. Synthesis of enones 6 with a gem-difluoroalkyl side chain. Synthesis of 7a. One-pot synthesis of 7a. Synthesis of enones 6a–e. Preparation of different imidazo[1,2-a]-N-heterocyclic derivatives

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• oligosaccharides including those containing both 1,2-cis and 1,2-trans linkages, branching sequences and sulfate esters. For example, a four component preactivation-based one-pot synthesis was designed to synthesize Globo-H, an important tumor-associated carbohydrate antigen (Scheme 18) [60]. Globo-H

• ; then 96, and triethyl phosphite; (b) p-TolSCl/AgOTf, −60 °C; then 99. One-pot synthesis of Globo-H hexasaccharide 105 using building blocks 101, 102, 103 and 104. Synthesis of (a) oligosaccharides 109–113 towards (b) 30-mer galactan 115. Reagents and conditions: (a) TTBP, 4 Å MS, CH2Cl2, p-TolSCl

Main group mechanochemistry

• Agota A. Gečiauskaitė and
• Felipe García

Beilstein J. Org. Chem. 2017, 13, 2068–2077, doi:10.3762/bjoc.13.204

• ) (Cp′ = C5Me4(n-Pr)). Mechanochemical synthesis of the Ar-BIAN ligands and indium(III) complexes (top). One-pot synthesis of an indium complex (bottom). Synthesis of germanes from germanium (Ge) or germanium oxide (GeO2). Ball-milling nucleophilic substitution reactions to produce acyclic and cyclic

Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

• Hao Wang,
• Cui Chen,
• Weibing Liu and
• Zhibo Zhu

Beilstein J. Org. Chem. 2017, 13, 2023–2027, doi:10.3762/bjoc.13.200

• , Maoming 525000, P. R. China. Fax: +86-668-2923575; Tel: +86-668-2923956 10.3762/bjoc.13.200 Abstract We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes

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