Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams

• Valentina Giraldi,
• Giandomenico Magagnano,
• Daria Giacomini,
• Pier Giorgio Cozzi and
• Andrea Gualandi

Beilstein J. Org. Chem. 2024, 20, 2461–2468, doi:10.3762/bjoc.20.210

• investigated whether this protocol could be adapted to other lactams, allowing for a practical synthesis of bicyclic structures. The resulting bicyclic lactam substrate could serve as a foundation to access pyrroloisoquinoline alkaloids [50][51]. The model substrate 14 was synthesized in a two-step process

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• pointed out, though for the first time truxene was reported in 1894 by Kipping [9], whereby 3‐phenylpropionic acid in situ cyclized under acidic conditions to indan‐1‐one which under the same conditions offered a mixture of both isomers, that is truxene as well as isotruxene. However, the practical

• synthesis of only truxene was established by Dehmlow’s research group in 1997 [10]. Remarkably, one of the advantages of truxene over the other polyaromatic hydrocarbons (PAHs) is the presence of three benzylic positions, that generally permit to assemble a myriad of functionalized truxene-based

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

• Matteo Gasparetto,
• Balázs Fődi and
• Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

• crucial function in many biological processes. Due to their bifunctional character, they have been also used for combinatorial chemistry purposes, such as the preparation of DNA-encoded chemical libraries. We developed a practical synthesis for α-heteroaryl-α-amino acids starting from an array of small

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

• and practical synthesis of 2-arylpyridines. The reaction starts with the formation of arylated pyridine N-oxide 116 by reaction of pyridine N-oxide 9 with the arylboronic ester 114 in the presence of Cu catalyst and base which is followed by deoxygenation to furnish the desired product 115 (Scheme 22b

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

• Qian-Ci Gao,
• Yi-Fei Li,
• Jun Xuan and
• Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

NaI/PPh₃-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

• Dan Liu,
• Yue Zhao and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

• by these advances, we developed here a visible light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides under NaI/PPh3 catalysis, for the most efficient and practical synthesis of quaternary oxindoles (Scheme 1b and 1c). It should be noted that during the finalization of this

New synthesis of a late-stage tetracyclic key intermediate of lumateperone

• Mátyás Milen,
• Bálint Nyulasi,
• Tamás Nagy,
• Gyula Simig and
• Balázs Volk

Beilstein J. Org. Chem. 2022, 18, 653–659, doi:10.3762/bjoc.18.66

• ] for the resolution of compound (±)-10, a direct intermediate of lumateperone, easily available from (±)-9a, we aimed to elaborate a new, practical synthesis of the latter. First, we envisaged a new synthetic route to the racemic key intermediate (±)-9a, significantly shorter than those described

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• challenge and practical synthesis is still missing in the literature. Its accessibility may enrich the arsenal of available tools for enzyme inhibitor design by increasing the number of hydrogen bonding donor and acceptor groups at the same side of the backbone, which may result in a tight binding with

Chemoselective N-acylation of indoles using thioesters as acyl source

• Tianri Du,
• Xiangmu Wei,
• Honghong Xu,
• Xin Zhang,
• Ruiru Fang,
• Zheng Yuan,
• Zhi Liang and
• Yahui Li

Beilstein J. Org. Chem. 2022, 18, 89–94, doi:10.3762/bjoc.18.9

• , Scheme 3). The results indicate that this N-acylation reaction of indole has great potential in practical synthesis. Some control experiments were conducted to explore the reaction mechanism of this transformation (Scheme 4). When S-methyl decanethioate (2i) was adopted without Cs2CO3, no decomposition

A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

• Yuki Yamamoto,
• Akihiro Tabuchi,
• Kazumi Hosono,
• Takanori Ochi,
• Kento Yamazaki,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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

• diseases [60]. The reaction of the enzymatic transglycosylation was used by Krenitsky et al. in the practical synthesis of nelarabine (vide supra), whereas the preparation of KR has been reported earlier (i) by employing the selected whole E. coli cells [61][62] and briefly described (ii) by using the

Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols

• Tatsuya Kumon,
• Miroku Shimada,
• Jianyan Wu,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184

• best of our knowledge, there are no reports on the practical synthesis of disubstituted 2-fluoroalkylated indenols so far. Transition-metal-catalyzed carbocyclization reactions of alkynes with benzene derivatives having a leaving group X (X = Br, I, OTs, B(OH)2) have been widely considered as one of

• . Despite their effective advantages, on the other hand, the reports on cycloaddition reactions with fluorine-containing alkynes for the construction of fluoroalkylated indene derivatives are rare [21][26]. Recently, our group has reported the first practical synthesis of fluoroalkylated indenol derivatives

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles

• Ken Tamamoto,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 2375–2383, doi:10.3762/bjoc.14.213

• apparatus [24] or reductive couplings with various carbonyl compounds [25], leading to good yields of versatile CF2CF2-containing substances. However, many obstacles to practical synthesis remain, e.g., the use of 1,2-dibromotetrafluoroethane (Halon-2402) with ozone depletion and global warming potentials

One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates

• Jun Ki Kim,
• Hwan Jung Lim,
• Kyung Chae Jeong and
• Seong Jun Park

Beilstein J. Org. Chem. 2018, 14, 243–252, doi:10.3762/bjoc.14.16

• , Korea Translational Research Branch, National Cancer Center, 323 Ilsan-ro, Ilsandong-gu, Goyang-si Gyeonggi-do 10408, Korea 10.3762/bjoc.14.16 Abstract Herein, we describe a novel approach for the practical synthesis of tetrasubstituted thiophenes 8. The developed method was particularly used for the

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• keto-oximes 179 and 2-amino derivatives 180 are β2-adrenergic agonists tested for bronchodilating activity. The pterosin family are sesquiterpenoids naturally occurring in bracken fern (Pteridium aquilinum), some of them exhibit antibacterial and cytotoxic activity. A practical synthesis of pterosin A

Versatile synthesis of the signaling peptide glorin

• Robert Barnett,
• Daniel Raszkowski,
• Thomas Winckler and
• Pierre Stallforth

Beilstein J. Org. Chem. 2017, 13, 247–250, doi:10.3762/bjoc.13.27

• intraspecies interactions will give insight into the fundamentals of cell signaling and access to a rich source of novel natural products. We describe a practical synthesis of the modified dipeptide glorin (1, Figure 1), the assumed acrasin for many of the early-diverged species of social amoebae. While

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• pioneering works of Friedkin and co-workers (testing of 5-amino- and halogeno derivatives of uracil for TP from horse liver) and Heidelberger and co-workers (practical synthesis of 5-fluoro- and 5-trifluoromethyl-2'-deoxyurines) substrate properties of 5-substituted uracil derivatives were studied in a

A novel and practical asymmetric synthesis of dapoxetine hydrochloride

• Yijun Zhu,
• Zhenren Liu,
• Hongyan Li,
• Deyong Ye and
• Weicheng Zhou

Beilstein J. Org. Chem. 2015, 11, 2641–2645, doi:10.3762/bjoc.11.283

• route for the synthesis of (S)-dapoxetine (1) through this chiral auxiliary. Results and Discussion Herein, a novel and practical synthesis of 1 (Scheme 1) based on (S)-tert-butanesulfinamide (2) was developed. 3-(Naphthalen-1-yloxy)-1-phenylpropan-1-one (3), which was commercially available from J&K

Recent advances in copper-catalyzed asymmetric coupling reactions

• Fengtao Zhou and
• Qian Cai

Beilstein J. Org. Chem. 2015, 11, 2600–2615, doi:10.3762/bjoc.11.280

• coupling The biaryl motif is a key subunit in many natural products and axially chiral ligands. The classical Ullmann coupling is one of the most important methods for the practical synthesis of biaryls [14]. However, only few reports of an asymmetric version of the Ullmann coupling have been documented

Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant

• Dnyaneshwar N. Garad,
• Subhash D. Tanpure and
• Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

• for a practical synthesis of vernakalant. Keywords: APS-DMSO; imides; practical synthesis; radical-mediated; vernakalant; Introduction Cyclic imides are privileged pharmacophores and important building blocks for the synthesis of natural products, drugs, agrochemicals, advanced materials and

• developed protocol is wide and pure products could be obtained without column chromatographic purification, which makes it a commercially sustainable process. A practical synthesis of the drug vernakalant has been achieved using our one-pot imide forming process as one of the important steps. Currently, we

• (OAc)2 (10 mol %), ammonium persulfate (APS) (2 equiv), 1,4-dioxane (0.1 M), DMSO (5% v/v), 100 °C, 3 h in a Schlenk tube). A practical synthesis of vernakalant (11). Optimization studiesa. Imides from substituted/unsubstituted aromatic amines and succinic anhydridesa. Imides from substituted

Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization

• William H. Hersh

Beilstein J. Org. Chem. 2015, 11, 184–191, doi:10.3762/bjoc.11.19

• interference has also been described [24]. We recently reported the synthesis of a number of chiral disulfide sulfurizing reagents [25] and the results of the sulfurization of phosphite triesters in order to look for stereoselectivity [26]. In order to change such a method into a practical synthesis route for