One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

• Gui-Feng Kang and
• Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

• Kazuyuki Sato,
• Akira Kawasaki,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2020, 16, 1411–1417, doi:10.3762/bjoc.16.117

• FL (c) spectra at different solvent compositions of THF/H2O upon excitation at 365 nm (1.0 × 10−5 M); (d–f) F-BKI 9b: photograph (d), UV–vis (e), and FL (f) spectra at different solvent compositions of THF/H2O upon excitation at 380 nm (1.0 × 10−5 M). Selective fluorination of isoxazoles and one-pot

• synthesis of 4-fluoroisoxazoles. One-pot reaction for the synthesis of 3,5-disubstituted 4-fluoroisoxazoles 3. aIsolated yield. bIsolated yield by using conventional heating (oil bath) at 150 °C for 1 h. Synthesis of BKIs 6 either from 1,3-diketones 1 or from isoxazoles 2. Synthesis of enaminoketones 5 and

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

• Xiaoming Ma,
• Suzhi Meng,
• Xiaofeng Zhang,
• Qiang Zhang,
• Shenghu Yan,
• Yue Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

• , triazolobenzodiazepines and tetrahydrochromeno[3,4-b]pyrrolizine (Scheme 2) [30][31][32][33][34][35][36][37][38][39]. Many of these scaffolds were synthesized through the combination of MCR and one-pot synthesis. A literature search indicated that a [3 + 2] cycloaddition-initiated method has also been used for the

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

• Ji Ma,
• Yubin Fu,
• Junzhi Liu and
• Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

• Ming-Xi Bi,
• Shuai Liu,
• Yangen Huang,
• Xiu-Hua Xu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

• . Recently, the development of efficient methods for the synthesis of pyrrolo[1,2-a]indol-3-one derivatives has attracted considerable attention. For instance, Song [21] and Liang [22] reported the one-pot synthesis of novel phosphorylated and sulfonylated pyrrolo[1,2-a]indol-3-ones from N-[(3-phenyl

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• and the carbohelicene moieties (Scheme 1) [16]. The approach focused on the regioselective one-pot synthesis of a 7-hydroxybenzo[b]phosphole derivative from an 3-alkoxyphenylzinc reagent, an alkyne, and dichlorophenylphosphine [17]. The hydroxy group of this key intermediate served as a handle for the

Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• exhibits unusual properties in nucleophilic reactions. This reagent was obtained [30][31][32] in high yield and with high purity by a one-pot synthesis from divinyl sulfide [33][34][35] and selenium dibromide. The structure of compound 1 suggests the possibility of formation of both seleniranium 2 and

• % yields, respectively. The one-pot synthesis of hitherto unknown bis(1,3-thiaselenol-2-ylmethyl) diselenide (8) in 90% yield from thiaselenole 1 was developed (Scheme 10). The reaction proceeded via the formation of thiaselenole selenocyanate 4, which was in situ converted into diselenide 8. This compound

• alkyl propiolates (77Se NMR data are included). One-pot synthesis of diselenide 8 from thiaselenole 1 (77Se NMR data are included). Synthesis of compounds 6a–j from diselenide 8. Results the reaction of thiaselenole 1 with KSeCN based on 1H NMR spectroscopy monitoring (Figure 1).a Supporting

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

• Faïma Lazreg,
• Marie Vasseur,
• Alexandra M. Z. Slawin and
• Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

• catalytic strategy for the one-pot synthesis of N-sulfonylamidines is described. The cationic copper(I) complexes were found to be highly active and efficient under mild conditions in air and in the absence of solvent. A copper acetylide is proposed as key intermediate in this transformation. Keywords

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• -bond formation A P–N bond formation reaction is easier to be done than a P–C bond formation because the construction of the latter involves reaction conditions that are not suitable for multifunctionalized precursors. On the other hand, the installation of P–N bonds is usually done via a “one-pot

• synthesis” protocol. The quaternary salt byproduct that is formed when using an amine as the base can be easily separated by filtration. Bis(phosphine)amines with a P–N–P framework are more flexible to manipulate than diphosphines with a P–C–P framework [98]. The P–N–P cone angle and geometry on the

Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin

• Thomas J. Cogswell,
• Craig S. Donald and
• Rodolfo Marquez

Beilstein J. Org. Chem. 2020, 16, 135–139, doi:10.3762/bjoc.16.15

• )-(+)-goniothalamin 2 and acylated aza-goniothalamin analogue 3 [14][15][16][17][18]. Extension of the two-pot methodology to include a variety of different aldehyde starting materials. One pot synthesis of benzyl carbamate 4 reported by Veenstra and co-workers [19]. Formation of diene 5 in 66% through a one pot

One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

• Valeriya G. Melekhina,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Vitaly S. Mityanov,
• Artem N. Fakhrutdinov,
• Arkady A. Dudinov,
• Vasily A. Migulin,
• Yulia V. Nelyubina,
• Elizaveta K. Melnikova and
• Michail M. Krayushkin

Beilstein J. Org. Chem. 2019, 15, 2840–2846, doi:10.3762/bjoc.15.277

• : condensation; dihydropyrrolone derivative; one-pot synthesis; pyrrolo[3,4-b]pyridine-4,5-diones; recyclization; Introduction Derivatives of pyrrolo[3,4-b]pyridin-5-one are known for their broad-spectrum biological activity [1][2][3]. One example includes a family of compounds based on this fragment that was

• to give the crude enaminone 7a as a brown solid. The obtained residue was then heated in an AcOH/HCl mixture to give the target pyrrolopyridinone 1a. In addition, the described one-pot synthesis, besides from being more straightforward, provided better yields as compared to the standard two-step

Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study

• Sergey A. Dobrynin,
• Igor A. Kirilyuk,
• Yuri V. Gatilov,
• Andrey A. Kuzhelev,
• Olesya A. Krumkacheva,
• Matvey V. Fedin,
• Michael K. Bowman and
• Elena G. Bagryanskaya

Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259

• observed in a one-pot synthesis from cyclopentanone, dimethyl fumarate and ammonium acetate. This multistep reaction includes 1,3-dipolar cycloaddition of dimethyl fumarate to the cyclic azomethine ylide formed in situ from cyclopentanone and ammonia. The polycyclic amine product was easily converted into

• carbonyl compounds for the synthesis of heterocyclic compounds has been repeatedly demonstrated [2][3]. We recently used a domino reaction of amino acid, ketone and dimethyl fumarate for the one-pot synthesis of a substituted pyrrolidine, which then was converted into a reduction-resistant pyrrolidine

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• al. developed a programmable enantioselective one-pot synthesis of molecules with eight stereocentres greatly improving the efficiency of natural product synthesis [83]. Each of these natural products are biologically active, hence their total synthesis will allow further characterisation of their

Friedel–Crafts approach to the one-pot synthesis of methoxy-substituted thioxanthylium salts

• Kenta Tanaka,
• Yuta Tanaka,
• Mami Kishimoto,
• Yujiro Hoshino and
• Kiyoshi Honda

Beilstein J. Org. Chem. 2019, 15, 2105–2112, doi:10.3762/bjoc.15.208

• . Keywords: Friedel–Crafts reaction; metal-free conditions; one-pot synthesis; photoredox catalyst; thioxanthylium salt; Introduction Thioxanthylium salts are one of the important structural motifs found in biologically active compounds and photochemical materials [1][2][3][4][5][6][7][8]. Owing to these

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

• Hai-Yun Huang,
• Haoran Li,
• Thierry Roisnel,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204

• 58–74% yields. Then, the one-pot synthesis of α,β-di(hetero)arylated 5,6-dihydropyrrolo[3,2,1-ij]quinolines was attempted (Scheme 3). The use of a larger amount of aryl bromides (3 equiv) provided the target diarylated lilolidines 20–22 in good yields. Under these conditions, the mono-arylated

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• ), a new quinazolinone derivative in 40% yield (Scheme 6). Notably, these heterocycles are known for their use as antitumor [101], anticonvulsant [102] or epidermal growth factor receptor tyrosine kinase inhibitory agents [103], JNK inhibitors [104] or 5-HT3 antagonists [105]. Earlier, a one-pot

• synthesis of an analogous compound was accomplished by Sayahi et al. starting from isothiocyanates in the presence of CuBr [106]. As aforementioned, in some cases only isothiocyanate 8 was detected and/or isolated. Thus, in order to gain mechanistic insights on the generation of 3a, we performed a series of

Different reactivity of phosphorylallenes under the action of Brønsted or Lewis acids: a crucial role of involvement of the P=O group in intra- or intermolecular interactions at the formation of cationic intermediates

• Stanislav V. Lozovskiy,
• Alexander Yu. Ivanov and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1491–1504, doi:10.3762/bjoc.15.151

• mixture with morpholine leading to amide Z-11o. Multigram-scale one-pot synthesis of indane 12d from 2-methylbut-3-yn-2-ol. 1H, 13C, and 31P NMR monitoring of AlCl3-promoted reactions of allene 1a leading to compounds E-14 or 15 at room temperature. Plausible reaction mechanism A for the formation of

• -pot synthesis of indane 12d starting from 2-methylbut-3-yn-2-ol (Scheme 7, see procedure in Supporting Information File 1). The first stage of this procedure gave allene 1a, which was dissolved in CH2Cl2 and subjected to reaction with p-xylene under the action of AlCl3. Finally, methanolysis of the

• complex mixtures of oligomeric compounds. In the same reaction with benzene, allene 1b afforded alkene Z-11n in high yield (Scheme 5). The use of morpholine for quenching of the superacidic reaction mixture gave amide Z-11o in the reaction of 1a with benzene (Scheme 6). We also conducted a large-scale one

One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

• Christina Görgen,
• Katharina Boden,
• Guido J. Reiss,
• Walter Frank and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1360–1370, doi:10.3762/bjoc.15.136

• ] specifically have been published employing a cyclizing addition of an acylhydrazone to the carbonyl group as a ring-forming reaction [32][33][34][35][36][37][38][39][40], their diversity-oriented one-pot synthesis in a multicomponent approach has remained unexplored to date. In the course of our program

• additionally corroborated by X-ray structure analysis showing that the assignment of intermediate 5a was not a fully unsaturated pyrazole (Figure 4) [53]. Therefore, we set out to optimize the one-pot synthesis of 1,5-diacyl-5-hydroxypyrazolines by choosing the model reaction of phenylglyoxylic acid (1a

• –cyclization sequence of (hetero)arylglyoxylic acids, oxalyl chloride, arylacetylenes, and hydrazides does not form aromatic pyrazoles, but rather 1,5-diacyl-5-hydroxypyrazolines, i.e., the aromatizing elimination of water does not occur under these neutral conditions. This novel one-pot synthesis of 1,5

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• -lactam, albeit functionalized in the side chain. The one-pot synthesis of the β-lactam steroid was achieved via the Ugi 3-component-4-center reaction using the dehydrocholic aldehyde 1 as carbonyl component. This variation of the Ugi reaction including a β-amino acid component allows the formation of the

• (cages) by multiple multicomponent macrocyclizations based on the Ugi-4CR [73][75]. One-pot synthesis of steroidal cages by double Ugi-4CR-based macrocyclizations [76].

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

• Angélica de Fátima S. Barreto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

• for the synthesis of molecular cages was described [50]. The approach was based on macromulticycle connectivities through bridgeheads. For the macrocyclization reaction, metal-template-driven and dilution conditions were used. These conditions allowed one-pot synthesis including aryl, heterocyclic

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• Marius Kunkel Sebastian Polarz University of Konstanz, Universitätsstrasse 10, 78467 Konstanz, Germany 10.3762/bjoc.15.87 Abstract An efficient one-pot synthesis for Janus-type fullerenol derivatives and how to characterize them is reported. This synthesis provides access to asymmetrically

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• ester cages of type 22 [64]. Mechanochemical synthesis of borasiloxane-based macrocycles. Mechanochemical synthesis of 2-dimensional aromatic polyamides. Nitschke’s tetrahedral Fe(II) cage 25. Mechanochemical one-pot synthesis of the 22-component [Fe4(AD2)6]4− 26, 11-component [Fe2(BD2)3]2− 27 and 5

Selectivity in multiple multicomponent reactions: types and synthetic applications

• Ouldouz Ghashghaei,
• Francesca Seghetti and
• Rodolfo Lavilla

Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46

• -based MCRs. In this way, the selective formation of intermediate B, leads to the following MCR processes based in different isocyanide MCRs. This approach made possible a remarkable 8-CR process for the one-pot synthesis of compounds with up to 11 diversity points. A conceptually distinct approach for