Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• (hetero)arylboronic acid 111 was reported. The use of a catalytic amount of CuCl and MeOLi as base in CH3CN as solvent was recognized as the optimized conditions. This strategy provided a new procedure for the one-pot synthesis of fully decorated 1,2,3-triazole derivatives 112 in good to excellent yield

Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines

• Alexei N. Izmest’ev,
• Dmitry B. Vinogradov,
• Natalya G. Kolotyrkina,
• Angelina N. Kravchenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2021, 17, 1141–1148, doi:10.3762/bjoc.17.87

• imidazo[4,5-e]thiazolo[3,2-b]triazines 4a–n into imidazo[4,5-e]thiazolo[2,3-c]triazines 5a–n. One-pot synthesis of compounds 5a,b,h,i from imidazo[4,5-e]triazines 3a,b. Plausible mechanism of the formation and the rearrangement of compounds 4 into isomers 5. Results for the screening of the reaction

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

• Asha Budakoti,
• Pradip Kumar Mondal,
• Prachi Verma and
• Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

• allylisilane 152. Further manipulation of functional groups of 153 leads to the synthesis of (−)-dactyloide (Scheme 36) [71]. The one-pot synthesis of a 2,6-disubstituted THP was reported by Minehan and co-workers and involved treating 3-iodo-2-[(trimethylsilyl)methyl]propene with an aldehyde in the presence

• Alder’s chair-like transition state 227 in which the (Z)-alkene accounts for the trans-stereocontrol at the C3 position and equatorial iodide addition accounts for the cis-stereocontrol at the C4 position, as shown below in Scheme 54. The one-pot synthesis of tetrahydropyran by utilizing the Babier–Prins

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

• Geetanjali S. Sontakke,
• Rahul K. Shukla and
• Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

• isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and

• derivatives, we performed a sequential one-pot synthesis by combining a Cu(I)-catalyzed “Click” reaction of phenylacetylene (7) with TsN3 and a metal-free C2-heteroarylation of quinoline N-oxide (1a, Scheme 6b). Remarkably, the yield of the desired product 3a in the one-pot synthesis (80%) was comparable to

• isoquinoline N-oxide. Gram-scale and one-pot synthesis. Proposed mechanism. Optimization of the reaction conditions.a Supporting Information Supporting Information File 220: Experimental details. Funding The activity was generously supported by Science and Engineering Research Board (SERB), India: CRG/2019

Decarboxylative trifluoromethylthiolation of pyridylacetates

• Ryouta Kawanishi,
• Kosuke Nakada and
• Kazutaka Shibatomi

Beilstein J. Org. Chem. 2021, 17, 229–233, doi:10.3762/bjoc.17.23

• lithium pyridylacetates undergo decarboxylative fluorination upon treatment with an electrophilic fluorination reagent to afford fluoromethylpyridines under catalyst-free conditions. Furthermore, we demonstrated the one-pot synthesis of fluoromethylpyridines from methyl pyridylacetates by saponification

• , entry 11). In the absence of MS 4 Å, the yield of 2a was diminished even when the reaction was carried out in THF (Table 1, entry 12). With the optimized reaction conditions in hand, we examined the one-pot synthesis of 2a from methyl ester 7a. Methyl 2-pyridylacetate 7a were saponified with lithium

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• cited therein). The classical two-stage version of the enzymatic transglycosylation reaction [16][17][18][19][20], as well as one-pot synthesis, and the more sophisticated option employing two cross-glycosylation transformations for nucleoside synthesis [23][24][25][26][27], seemed less attractive and

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• NPs. A one-pot synthesis method was used to both deposit Pd salts and reduce them into NPs onto the support material. First, PdCl2 was mixed for 15 min with either ChNC or ChsNC in an acidic aqueous medium to form a dark yellow mixture. This step facilitated coordination of Pd salts onto the support

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

• Thomas Schneider,
• Michael Keim,
• Bianca Seitz and
• Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

• theory), but also represent powerful 1,3-biselectrophiles. Thus, Diels–Alder reactions followed by an intramolecular SE(Ar) reaction of the α-(trifluoromethyl)iminium functional group were achieved as a two-step one-pot synthesis. On the other hand, an electrophilic (Markownikow type) addition of the

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

• Ksenia I. Kaskevich,
• Anastasia A. Babushkina,
• Vladislav V. Gurzhiy,
• Dmitrij M. Egorov,
• Nataly I. Svintsitskaya and
• Albina V. Dogadina

Beilstein J. Org. Chem. 2020, 16, 1947–1954, doi:10.3762/bjoc.16.161

• uracil ring, leading to the formation of 7-oxopyrimidines. Structure of ritanserin and setoperone drugs. One-pot synthesis of 5(7)-oxothiazolopyrimidine-6-carbonitriles. Synthesis of thiazolopyrimidine-5-ones through the reaction of 2-aminothiazoles with ethyl acetoacetate. Synthesis of 2-(benzo[d

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• intramolecular nucleophilic attack to the terminal imino group of 9a, provides cyclized adduct 10a, and finally pyrimidine derivative 7a by aromatization/elimination of NH3. To the best of our knowledge, this is the first one-pot synthesis of functionalized pyrimidines using phenacyl azides as the sole starting

• in Supporting Information File 1. One-pot synthesis of 2,5-diarylpyrazines (A) (path a) or 2-aroyl-(4 or 5)-aryl-(1H)-imidazoles (B) (path b), or 2,4-diaroyl-6-arylpyrimidines (C) (path c) in DES from phenacyl azides (rt = room temperature). Transformation of phenacyl bromide (1a) in ChCl/Gly into

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

• Haruyasu Asahara,
• Minami Hiraishi and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

• (CH), 129.3 (CH), 134.8 (C), 138.1 (C), 139.8 (C), 142.3 (C), 158.9 (C). One-pot synthesis of 3-arylated-4-nitrophenol 5b To a solution of Danishefsky’s diene (2, 129.2 mg, 0.75 mmol) in toluene (1 mL), nitrostyrene 1b (90.0 mg, 0.50 mmol) was added, and the resulting mixture was heated at 120 °C for

• structure of nitroalkenes 1b and 1d. Synthetic scheme of the 3-arylated-4-nitrophenols 5. Conversion from 3a to 4a and one-pot synthesis of 4a. Deuteration of cyclohexanone 4a. A plausible mechanism for the formation of 5a. Optimization of the reaction conditions for the Diels–Alder reaction.a Aromatization

• of cyclohexanone 4a. One-pot synthesis of 3-arylated-4-nitrophenols 5. Supporting Information Supporting Information File 124: Spectral data for 5b–f, NMR spectra (1H, 13C, and DEPT) for 4a and 5a–f, and crystallographic data for 4a. Acknowledgements The authors appreciate the kind assistance

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• , dichloromethane, toluene, and n-hexane/dichloromethane. While no reaction was observed in diethyl ether, the best conversion was achieved in dichloromethane. Benzene was not used as a solvent because of having toxic and carcinogenic effects. Herein, we report mild reaction conditions for the one-pot synthesis of

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• -tethered benzothiophenone derivatives via incorporation of sulfur. To the best of our knowledge, this is the first report of one-pot synthesis of novel β-carboline-tethered benzothiophenones and evaluation of their light-emitting properties. In this regard, detailed studies are presented and discussed

• found to be slow reacting and produced 2aA in a lower yield (42%). From the perspective of green chemistry, one-pot reactions are preferred as less waste is generated due to the avoidance of work-up, isolation, and purification of intermediates [66]. Accordingly, the feasibility of a one-pot synthesis

• by the results obtained from the one-pot synthesis of β-carboline C-1 substituted benzothiophenone derivatives, we were interested if the scope of this one-pot strategy could be extended for the synthesis of β-carboline C-3-tethered benzothiophenones (Scheme 5). Thus, the Claisen–Schmidt condensation

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

• Moustafa Sherief Moustafa,
• Ramadan Ahmed Mekheimer,
• Saleh Mohammed Al-Mousawi,
• Mohamed Abd-Elmonem,
• Hesham El-Zorba,
• Afaf Mohamed Abdel Hameed,
• Tahany Mahmoud Mohamed and
• Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

• Chemistry, Faculty of Science, Minia University, Minia 61519, Egypt Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, Giza 12211, Egypt 10.3762/bjoc.16.142 Abstract An efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-1,3,5-triazine-2,4-diamine derivatives was

• -2,4-diamines; one-pot synthesis; X-ray crystallography; Introduction The family of triazines is of considerable interest in fields related to organic and medicinal chemistry. 2,4-Diaminotriazines are privileged scaffolds exhibiting diverse biological activities such as antibacterial [1], anti-HSV-1

• required temperature control and showed dependence on the amine nucleophile reactivity [27]. Another route involved the reaction of substituted biguanidines with acetic anhydrides, chlorides or carboxylates [11][28][29][30][31]. Liu et al. [32] reported a one-pot synthesis of N2,6-disubstituted-1,3,5

Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• 21, was unsuccessful and no tricyclic product was formed. Bonnet-Delpon and co-workers reported the one-pot synthesis of several CF3-containing N-tethered amines in good yields (54–86% over 2 steps) [49]. These products were subjected to metathesis reactions in the presence of Grubbs catalyst

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• the homogeneous photocatalyst. The flow synthesis also prevented the formation of a chlorinated byproduct identified on the batch resins as an intermediate, and purification could be applied to wash out reactants from the first step of the one-pot synthesis, a potentially useful synthetic advantage of

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