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

• %), K2CO3 (2 equiv) and NaOAc (1 equiv) in MeCN (3 mL) under nitrogen for the Heck reaction. Isolated yield. Plausible mechanism for the synthesis of 9a. Optimization of the one-pot reaction conditions.a Supporting Information Supporting Information File 46: General reaction procedures, compound

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• application in the synthesis of quinazolin-4-(3H)-ones by the one-pot reaction between alcohols and 2-aminobenzamide under an oxidative quenching, visible light irradiation using air or oxygen as oxidant (60–81% yields). The authors propose the generation of the superoxide radical anion with the MOF. The

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• enyne substrates, the one-pot reaction manifold enabled the anchorage of non-steroidal spirocyclic moieties at C-17. The procedure proved efficient and stereoselective with mestranol and lynestrenol derivatives incorporating a 2-tetrahydrofuranyl spirocycle at C-17. It was more difficult with 2-oxepanyl

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

• Yong Li,
• Zheng Huang,
• Jia Xu,
• Yong Ding,
• Dian-Yong Tang,
• Jie Lei,
• Hong-yu Li,
• Zhong-Zhu Chen and
• Zhi-Gang Xu

Beilstein J. Org. Chem. 2020, 16, 663–669, doi:10.3762/bjoc.16.63

• has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods. Keywords: Dieckmann cyclization; multicomponent reactions; nitrogen heterocycles; one-pot reaction; Ugi reaction; Introduction Nitrogen-containing heterocycles

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• -monosubstituted dipyrrin 3a, was obtained via a one-pot reaction in 18% yield (in three steps from 2). On the other hand, the β,β'-diethynyl-substituted BODIPY derivatives 5a and 6a, were synthesized by a similar gold-catalyzed reaction of unsubstituted BODIPY 1a in 38% and 2% yields, respectively, in the

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

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

• Vânia F. Pais,
• Tristan Neumann,
• Ignacio Vayá,
• M. Consuelo Jiménez,
• Abel Ros and
• Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

• 5 a Pd-catalyzed one-pot reaction consisting of a borylation and Suzuki coupling was applied. Thus, starting from 1-chloroanthracene (4) and using SPhos/Pd2dba3 (8:1) as the catalyst, a full conversion to the Miyaura-type borylated intermediate was achieved (TLC analysis) after 5 hours at 110 ºC

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• ; mitochondrial probe; near-infrared (NIR) dyes; one-pot reaction; silicon rhodamines; Introduction Since their first synthesis by Fu and co-workers in 2008 [1], silicon xanthenes and the subsequently developed silicon rhodamines (SiR) have drawn a lot of attention as attractive fluorescence dyes offering a

Synthesis of benzo[d]imidazo[2,1-b]benzoselenoazoles: Cs₂CO₃-mediated cyclization of 1-(2-bromoaryl)benzimidazoles with selenium

• Mio Matsumura,
• Yuki Kitamura,
• Arisa Yamauchi,
• Yoshitaka Kanazawa,
• Yuki Murata,
• Tadashi Hyodo,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2019, 15, 2029–2035, doi:10.3762/bjoc.15.199

• have been reported so far (Scheme 1). Zeni et al. reported the synthesis of imidazoselenoazole using a three-step one-pot reaction of N-alkynylimidazoles with selenium involving the electrophilic intramolecular cyclization of acetylenic compounds (Scheme 1, reaction 1) [6]. Zeni et al. also developed a

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• conveniently by means of a macrocyclic condensation reaction between N-functionalized 3,6-dihydroxyphthalimides and 3,6-dichlorotetrazine under mild conditions in a one-pot reaction manner. The novel macrocycles exist as a mixture of rapidly interconvertible conformers in solution while in the solid state they

• operational one-pot reaction fashion on the basis of a nucleophilic aromatic substitution reaction [23][24][25][26][27][28][29][30][31]. To prepare functionalized corona[6]arenes using diethyl terephthalate as a starting material, we observed, however, the formation of a mixture of macrocyclic isomers because

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

• -benzenedicarboxylate), Puthiaraj and co-workers have unprecedently discovered the catalytic activity of this metal-organic framework (MOF) for the synthesis of imidazo[1,2-a]pyridines [100]. The three-component, one-pot reaction between 1, 3 and nitromethane (10, Scheme 5) involved an intermolecular aza-Michael

• catalytic activity exhibited by Cu(0) NPs Chenglong et al. have reported an efficient, three-component one-pot reaction for the synthesis of imidazo[1,2-a]pyridines [111]. The protocol enjoyed a solvent-free domino reaction between compounds 3, 1 and 2 under nitrogen atmosphere at 120 °C (Scheme 15

• been tried with various Cu(I)- and Cu(II)-based catalysts but the use of a mixed nano-CuO/CuAl2O4 and ᴅ-glucose system has resulted in appreciable yields. This three-component one-pot reaction involved 2-AP, phenylacetylene and substituted benzaldehydes as the starting substrates (Scheme 34). The

An azobenzene container showing a definite folding – synthesis and structural investigation

• Abdulselam Adam,
• Saber Mehrparvar and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2019, 15, 1534–1544, doi:10.3762/bjoc.15.156

• strategy and we tried to synthesize the chiral foldable container 10 in a one pot reaction. For this purpose, the platforms 2a and 3a and the dibromide 9 were dissolved in acetonitrile in the ratio 1:1:2.2. To this solution potassium carbonate as base was added and the whole mixture was refluxed for one

• -isomer (Figure 8). Conclusion In conclusion, we were able to synthesize a foldable container consisting of two different types of Lissoclinum macrocyclic peptides which are connected via two azobenzene units. The synthesis of this container was achieved by a one pot reaction of the two imidazole

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

• been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

• Andrew T. King,
• Hugh G. Hiscocks,
• Lidia Matesic,
• Mohan Bhadbhade,
• Roger Bishop and
• Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

• , NSW, 2232, Australia Mark Wainwright Analytical Centre, University of New South Wales, Sydney, NSW, 2052, Australia, School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia 10.3762/bjoc.15.134 Abstract The one-pot reaction of 2,6-bis(diphenylmethyl)-4-methoxyaniline with tert

• . [12] (Scheme 1). Herein, we report the unexpected product derived from 5 under the reaction conditions described in Scheme 1. The unusual crystal packing present in this 3H-indazole product was also analysed. Results and Discussion The one-pot reaction of compound 5 with tert-BuONO and DABSO in the

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• investigate the synthesis of bambusuril analogs in which glycoluril and chromophoric units alternate. Here we describe the first results of our efforts. Results and Discussion The preparation of the macrocycles was based on a one-pot reaction of 2,4-dimethylglycoluril and m-xylylene dibromide, a structurally

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

• in a remarkable one-pot reaction sequence, which involved the incorporation of 13 building blocks and the formation of 20 new bonds without the need of isolating any intermediate in the process. Wessjohann and co-workers demonstrated that the MiBs strategy could be easily used to obtain several

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

• (1H-13C-CP) with structure of substituent, d) ATR–IR. Reaction scheme for the one-pot reaction of C60Cl6 to produce Janus-type fullerenols (OH)19+/−3C60(HNR)5. Scope of the reaction and isolated yields. Supporting Information Supporting Information File 358: General methods and characterization data

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

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

• prepared simultaneously in a one-pot reaction starting from 38 components (Figure 15). In 2015, Mal and co-workers described a multicomponent Biginelli [85] reaction following a subcomponent synthesis under mechanochemical conditions. They have developed a method in which dihydropyrimidone synthesis was

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

• Kirill B. Polyanskii,
• Kseniia A. Alekseeva,
• Pavel V. Raspertov,
• Pavel A. Kumandin,
• Eugeniya V. Nikitina,
• Atash V. Gurbanov and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2019, 15, 769–779, doi:10.3762/bjoc.15.73

• alkali in the last step, which provides the target high-purity imidazolidine in 85–87% yield. We stress that there is no need for the isolation and purification of intermediate substances. The introduction of Ru-indenylidene complex 8 in one-pot reaction with adduct 9 followed by reaction with styrenes

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

• Yue Zhong,
• Wen-Yu Wu,
• Shao-Peng Yu,
• Tian-Yuan Fan,
• Hai-Tao Yu,
• Nian-Guang Li,
• Zhi-Hao Shi,
• Yu-Ping Tang and
• Jin-Ao Duan

Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26

• , which indicated that the reaction was strongly influenced by steric hindrance. It was noteworthy that this sequential one-pot reaction could be carried out on the gram scale (Scheme 4). We selected 2-iodotoluene and 2-bromo-4,5-dimethoxybenzoyl chloride as substrates. When the reaction of 2-iodotoluene

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• on the 1H-imidazo[2,1-a]isoindolone skeleton, Hosseini-Zare et al. reported the synthesis of new 2,3-diaryl-5H-imidazo[2,1-a]isoindol-5-ones via the one pot reaction of 1,2-diketones, 2-formylbenzoic acid and ammonium acetate [15]. These methodologies usually use toxic solvents such as benzene [16

DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives

• Soumitra Guin,
• Raman Gupta,
• Debashis Majee and
• Sampak Samanta

Beilstein J. Org. Chem. 2018, 14, 2771–2778, doi:10.3762/bjoc.14.254

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

• Luce Mattio,
• Loana Musso,
• Leonardo Scaglioni,
• Andrea Pinto,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2018, 14, 2482–2487, doi:10.3762/bjoc.14.224

• protect the oxygen at C-4 [15]. We selected a benzyl protecting group, as it could be cleaved by catalytic hydrogenation together with the benzyl ester of L-phenylalanine in the ureidodipeptide fragment (see synthesis of compound 20) by a one-pot reaction. To increase the reaction rate toward O-alkylation

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

• Edwin Alfonzo,
• Jesse W. L. Mendoza and
• Aaron B. Beeler

Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

• -epoxide adduct 25 [35]. However, the one-pot reaction was highly successful with three electron-rich benzyl alcohols 26, 27, and 28 all bearing multiple oxygenation and with a large panel of electron-rich aldehydes (Figure 2). The reaction was highly successful even when both partners were poly-oxygenated

Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

• Aderonke Ajibola Adeyemo and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2018, 14, 2242–2249, doi:10.3762/bjoc.14.199

• sophisticated heterobimetallic supramolecular architectures in a one-pot reaction and their functional properties are currently being explored [55][62][63][64][65][66][67][68][69][70]. The incorporation of two different metal centers in a supramolecular architecture can impart different functional properties