Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams

• Tetsuya Sengoku,
• Koki Makino,
• Ayumi Iijima,
• Toshiyasu Inuzuka and
• Hidemi Yoda

Beilstein J. Org. Chem. 2020, 16, 2769–2775, doi:10.3762/bjoc.16.227

• understanding of the structure–cytotoxicity relationship [14]. Therefore, we were motivated to develop a new synthetic methodology for N-alkyl and N-phenyl derivatives 4 and 5 starting from 2 with 1. Results and Discussion Our studies began with an exploration of a promising substrate for the desired

A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates

• Olusesan K. Koleoso,
• Matthew Turner,
• Felix Plasser and
• Marc C. Kimber

Beilstein J. Org. Chem. 2020, 16, 1983–1990, doi:10.3762/bjoc.16.165

• synthetic methodology that could generate this conjugated N-acyliminium intermediate 2, that would not be dependent on conventional electrophilic activation modes (Scheme 2). In principle, a new method for its generation could greatly enhance the value of the allenamide building block, as well as

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

• Soundararajan Karthikeyan,
• Radha Krishnan Shobana,
• Kamarajapurathu Raju Subimol,
• J. Helen Ratna Monica and
• Ayyanoth Karthik Krishna Kumar

Beilstein J. Org. Chem. 2020, 16, 1579–1587, doi:10.3762/bjoc.16.130

• ) acetylation, (ii) azidation, and (iii) cycloaddition to produce IV–VIII. In spite of the broad scope and synthetic utility, it is evident that the multistep synthetic methodology is the only existing module for cycloaddition reactions. Our research group is focused on developing one-pot synthetic

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

• 100050, China 10.3762/bjoc.16.120 Abstract A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

• Alexander V. Nyuchev,
• Ting Wan,
• Borja Cendón,
• Carlo Sambiagio,
• Job J. C. Struijs,
• Michelle Ho,
• Moisés Gulías,
• Ying Wang and
• Timothy Noël

Beilstein J. Org. Chem. 2020, 16, 1305–1312, doi:10.3762/bjoc.16.111

• Alexander V. Nyuchev Ting Wan Borja Cendon Carlo Sambiagio Job J. C. Struijs Michelle Ho Moises Gulias Ying Wang Timothy Noel Micro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Het Kranenveld, Bldg 14 − Helix, 5600

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

• David Schönbauer,
• Carlo Sambiagio,
• Timothy Noël and
• Michael Schnürch

Beilstein J. Org. Chem. 2020, 16, 809–817, doi:10.3762/bjoc.16.74

• David Schonbauer Carlo Sambiagio Timothy Noel Michael Schnurch Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria Department of Chemical Engineering and Chemistry, Micro Flow Chemistry and Synthetic Methodology, Eindhoven University of Technology, Den

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

• nonalternant cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), which represent the topological subunits of fullerenes and exhibit high chemical, physical and biological activities [1][2][3][4][5][6][7][8][9][10]. Thanks to development in organic synthetic methodology, CP-PAHs with peripheral

The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

• Narasimhamurthy Rajeev,
• Toreshettahally R. Swaroop,
• Ahmad I. Alrawashdeh,
• Shofiur Rahman,
• Abdullah Alodhayb,
• Seegehalli M. Anil,
• Kuppalli R. Kiran,
• Chandra,
• Paris E. Georghiou,
• Kanchugarakoppal S. Rangappa and
• Maralinganadoddi P. Sadashiva

Beilstein J. Org. Chem. 2020, 16, 159–167, doi:10.3762/bjoc.16.18

• , yielding O-benzyl benzylcarbamothioate (4a) in 80% yield after 1 h (Table 1, method B, entry 1). A decreased amount of base reduced the yield slightly (Table 1, method B, entry 6). The versatility of the synthetic methodology was further investigated by reacting O-benzyl S-methyl dithiocarbonate (1a) with

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

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• acids significantly differ in terms of carbon atom economy and preparative simplicity although carbon-wasteless approaches do exist. For future use as starting materials in total syntheses of complex natural products synthetic methodology to orthogonally protected hydroxyglutamic acids were also

Design and synthesis of C₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

• Sambasivarao Kotha,
• Saidulu Todeti and
• Vikas R. Aswar

Beilstein J. Org. Chem. 2018, 14, 2537–2544, doi:10.3762/bjoc.14.230

• established with the help of 1H NMR, 13C NMR spectral data and was further supported by HRMS details (Scheme 3). Conclusion We have demonstrated a simple synthetic methodology to C3-symmetric star-shaped molecules containing propellane moieties at the periphery which may be useful for material science

Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines

• Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 1349–1369, doi:10.3762/bjoc.14.114

• -Henry reactions The catalytic asymmetric Henry reaction, also known as catalytic asymmetric nitroaldol reaction, constitutes a useful synthetic methodology towards chiral β-nitro alcohols [69][70]. This reaction and related aza-Henry reactions involving imines have been promoted by both metal catalysts

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

• Romain Sallio,
• Stéphane Lebrun,
• Frédéric Capet,
• Francine Agbossou-Niedercorn,
• Christophe Michon and
• Eric Deniau

Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46

• nucleophiles bearing a chiral auxiliary enabled an effective match effect between the diastereomeric ion pair formed by the nucleophile, the Michael acceptor and the cinchoninium salt. Further investigations on this synthetic methodology will be reported in due course. Examples of synthetic pharmacologically

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30

• synthetic methodology, and so in principle the locust bean gum approach should allow rapid access to a wide variety of more extended N-glycan structures. In their original publication Nishimura and co-workers first glycosylated the free OH at position 3 with 2,4-branched trisaccharide trichloroacetimidate

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• bond bioisosteres made the click reaction a valuable synthetic methodology for conjugation of bioactive molecules [7][8][9] aiming to improve their biological activities [4][10][11]. Discovery of copper(I) ion catalysis in azide–alkyne cycloadditions was decisive for applications of this reaction, as

Main group mechanochemistry

• Agota A. Gečiauskaitė and
• Felipe García

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

• obtained in small-scale via salt metathesis reactions due to poor starting material (SrI2 and K[Cp′]) solubility in ether solution. LAG provides a high yielding synthetic methodology circumventing the scalability issues associated with the inefficient diffusion of reactants in large-scale solution-based

Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

• Manuel Anselmo,
• Lisa Moni,
• Hossny Ismail,
• Davide Comoretto,
• Renata Riva and
• Andrea Basso

Beilstein J. Org. Chem. 2017, 13, 1456–1462, doi:10.3762/bjoc.13.143

• atmosphere was not essential, we therefore decided to test our synthetic methodology with an in house-made flow apparatus. The reaction coil was formed with 1 m of FEP tubing (internal diameter 0.8 mm) wrapped around a glass cylinder. Irradiation was obtained with strips of blue LEDs attached inside a hollow

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• ) has been isolated for the first time and fully characterized. Certain insights into the role of enolization equilibria in the formation and diastereomeric integrity of the CCR adducts has been obtained. The synthetic methodology described herein significantly expands the scope and tests the limits of

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

• Stephan Scheeff and
• Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

• . Keywords: anticancer agent; medicinal chemistry polyketides; synthetic methodology; total synthesis; Introduction The complex structures of polyketides continues to be a great challenge for synthetic chemists and has also been a key driver for the development of new methodologies [1][2][3][4][5][6][7][8

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• fenitrothion (Figure 4) were also investigated. Finally, compounds 1–4 were tested for their detoxification ability against the nerve agent soman. Results and Discussion Synthesis The regioselective disubstitution of diol 6 (Scheme 1) was the key step to access derivatives 2 and 3. The synthetic methodology

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

• Vinicius R. Campos,
• Ana T. P. C. Gomes,
• Anna C. Cunha,
• Maria da Graça P. M. S. Neves,
• Vitor F. Ferreira and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

• such synthetic methodology in porphyrin chemistry allowing the synthesis of new derivatives, containing β-arylvinyl substituents. Keywords: N-tosylhydrazones; Pd-catalyzed cross coupling; porphyrins; Introduction Porphyrin-type heterocycles are well known for their special role in several scientific

Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• derivatives [82][83]. On another hand, a greener synthetic methodology to bio-based polymers is to first synthesize a more reactive derivative of isosorbide and then perform the polycondensation reaction (Scheme 4). In this prospect a good candidate is the dicarboxymethyl isosorbide (DCI). In fact

Silica-supported sulfonic acids as recyclable catalyst for esterification of levulinic acid with stoichiometric amounts of alcohols

• Raimondo Maggi,
• N. Raveendran Shiju,
• Veronica Santacroce,
• Giovanni Maestri,
• Franca Bigi and
• Gadi Rothenberg

Beilstein J. Org. Chem. 2016, 12, 2173–2180, doi:10.3762/bjoc.12.207

• Raimondo Maggi N. Raveendran Shiju Veronica Santacroce Giovanni Maestri Franca Bigi Gadi Rothenberg Clean Synthetic Methodology Group, Dipartimento di Chimica, Università di Parma, Parco Area delle Scienze 17A, I-43124 Parma, Italy Van ’t Hoff Institute for Molecular Sciences, University of

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

• . This represents in principle a donor–acceptor–donor topology, suitable for further development toward molecular electronics. Studies employing the presented synthetic methodology and the concept of bridging oligophenothiazines with conjugating bridges of variable electronic nature are currently

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• the Kröhnke-type synthetic methodology [23][24] starting from azulene carbaldehydes (1) [25] and 2-acetylpyridine (Scheme 1). In the first step, the 1-azulenyl-2′-azachalcone precursor 2 is formed via a Claisen–Schmidt aldol condensation. This reaction was performed in an environmentally friendly