Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• carbonylative reduction approach of organic nitro compounds has been used for the synthesis of important industrial and pharmaceutical compounds such as indoles. In 1986, Cenini et al. reported a new synthetic method for indoles that involved 2-nitrostyrene derivatives. The reaction took place under drastic

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

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

• Milandip Karak,
• Cian R. Cloonan,
• Brad R. Baker,
• Rachel V. K. Cochrane and
• Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

• applications due to their improved solubility in aqueous systems. Assembly is achieved by integrating distinct carbohydrate, peptide, and polyprenyl phosphate building blocks. This modular synthetic method allows for the strategic substitution of constituent building blocks at different synthetic stages and

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• been reported involving the use of A3-bilanes [30][31] or dipyrromethane–dicarbinols [32], the modification of A4-porphyrins [33], or the reaction of pyrrole with different aldehydes [34]. In the present work, the applied synthetic method provided the A3B-porphyrins in a single-step reaction from

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• conditions, and allows easy installation of long-chain substituents at the C-2 position of the quinolone core. These characteristics of the synthetic method could be particularly attractive in the search of novel mimics of the Pseudomonas quorum-sensing signal molecules. The high activity of compounds 4d and

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• urgent need to develop diverse monofluoromethylation methods. In this context, Chen and his colleagues recently developed a concise photocatalytic procedure for achieving monofluoromethylation, as well as di- and trifluoromethylation of various alkenes (Scheme 25) [50]. The synthetic method also

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• under basic conditions, and expanded the synthetic method to N-substituted acylhydrazones [106][107] (Scheme 18). In the early development of 1,3-dipolar cycloadditions of azomethine imines, the acyclic azomethine imines were unstable and their in situ preparation required Brønsted acid or thermal

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• properties via an original mechanism of action. The increasing interest in studying ether lipids for fundamental and applied researches invited to review the methodologies developed to prepare ether lipids. In this review we focus on the synthetic method used for the preparation of alkyl ether lipids either

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• report, it augured the potential of RLT to be a general strategy in synthetic method development, with modern examples including new alkene addition reactions and decarboxylative functionalizations (Scheme 2). Recent applications of RLT in catalysis Upon the discovery and initial exploration of the RLT

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

• Alessio Regni,
• Francesca Bartoccini and
• Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

• common synthetic route to ergot alkaloids, providing an advantageous synthetic method for this class of natural products. Further studies on the utility of the decarboxylative radical cyclization and their applications are currently being investigated in our laboratory. (a) Transformations of DMAT to

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Mikhail E. Minyaev and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

• guanidine C. Finally, the intramolecular cyclization of the guanidine moiety and the carbonyl group leads to the target pyrimidine 9. After the general synthetic method for pyrimidines containing the allomaltol fragment had been established, the photochemical behavior of the obtained compounds 9 was

Sulfate radical anion-induced benzylic oxidation of N-(arylsulfonyl)benzylamines to N-arylsulfonylimines

• Joydev K. Laha,
• Pankaj Gupta and
• Amitava Hazra

Beilstein J. Org. Chem. 2023, 19, 771–777, doi:10.3762/bjoc.19.57

• reactions, and C–H functionalizations ([3] and references therein), leading to the synthesis of diverse nitrogen heterocycles of pharmaceutical relevance [4]. The traditional synthetic method for the preparation of N-arylsulfonylimines, similar to the preparation of N-arylimines, is based on the

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

• Louis Monsigny,
• Floriane Doche and
• Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

• ; palladium; synthetic method; Introduction Nowadays, fluorinated molecules represent an indispensable class of molecules in chemistry and in chemical biology. Thanks to the unique properties of the fluorine atom or fluorinated groups to modulate biological and physicochemical properties of the parent non

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• alternative approaches exist. The direct dehydrogenation of 1,4-dithiane is somewhat cumbersome [25], and, moreover, 1,4-dithiane (1) is surprisingly not available in large quantities at a reasonable cost, in spite of its apparent simplicity. Our lab has found that the synthetic method for dihydrodithiins

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

• is mediated by visible light irradiation. A wide range of substrates bearing different substituents and derived from ubiquitous carboxylic acids, including α-amino acids, were synthesized and examined under this very mild, efficient, and cost effective transition-metal-free synthetic method. These

• can operate as an efficient photoredox catalyst, providing an economical access to construct important oxindole scaffolds containing a quaternary carbon center. This synthetic method features a broad substrate scope, good functional group tolerance and operational simplicity. Mechanistic

On drug discovery against infectious diseases and academic medicinal chemistry contributions

• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

• patents just because of a lack of a simple synthetic method. Our contribution to alleviate this “blind spot” was an extensive exploration of the chemistry of alkoxypyrazoles (C) which provided synthetic building blocks useful to reach, amongst others, many new chemical entities with the general formula B

Dienophilic reactivity of 2-phosphaindolizines: a conceptual DFT investigation

• Nosheen Beig,
• Aarti Peswani and
• Raj Kumar Bansal

Beilstein J. Org. Chem. 2022, 18, 1217–1224, doi:10.3762/bjoc.18.127

• ; Fukui function; global hardness; nucleophilicity index; 2-phosphaindolizines; Introduction In 1988, we developed a simple synthetic method for the synthesis of 1,3-azaphospholo[1,5-a]pyridine derivative (1, R1 = Me, R2 = PhCO) from the reaction of 2-ethyl-1-phenacylpyridinium bromide with PCl3 and Et3N

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• , first reported in 1944 [3], a wide variety of catalytic systems are still being reported [4][5][6][7][8][9][10][11][12]. Electro-organic synthesis refers to an organic synthetic method combined with electrochemistry [13][14]. A striking feature in electro-organic synthesis is the use of electricity as a

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• -triisopropylphenyl)phosphinyl azide (17) gave the corresponding 2,3-dihydrobenzo[c][1,2]azaphosphole 1-oxide 18 in 51% and phosphonamidate 19 in 28% yield (Scheme 4). The synthetic method was applied occasionally [24]. P-Stereogenic 3-arylmethylidene-2,3-dihydrobenzo[c][1,2]azaphosphole 1-oxides 21 and 23 were

• -oxides 56a in 23% and 93 in 63% yields, respectively, showing the limited scope of the synthetic method (Scheme 17) [39]. Ring-closing metathesis (RCM) is an efficient strategy for the construction of cyclic compounds via the formation of a C=C bond [40][41], which can be reduced to the C–C bond. 2

• synthetic method showed very limited substrate scope. Only less bulky primary amines underwent the first aza-Michael addition and then intramolecular nucleophilic substitution. However, aromatic amines, aniline, 2,3-dihydro-1H-inden-4-amine, and the bulky aliphatic primary amine adamantylamine did not

Thiophene/selenophene-based S-shaped double helicenes: regioselective synthesis and structures

• Mengjie Wang,
• Lanping Dang,
• Wan Xu,
• Zhiying Ma,
• Liuliu Shao,
• Guangxia Wang,
• Chunli Li and
• Hua Wang

Beilstein J. Org. Chem. 2022, 18, 809–817, doi:10.3762/bjoc.18.81

• )2-bb-DTT, (TMS)2-bb-DST, and (TMS)2-bb-DSS as starting materials. The synthetic method described in this research not only provides a method for the synthesis of S- shaped double helicenes but also enriches the family of selenophene helicenes. Multiple intermolecular interactions and regular

Rapid gas–liquid reaction in flow. Continuous synthesis and production of cyclohexene oxide

• Kyoko Mandai,
• Tetsuya Yamamoto,
• Hiroki Mandai and
• Aiichiro Nagaki

Beilstein J. Org. Chem. 2022, 18, 660–668, doi:10.3762/bjoc.18.67

• conventional batch technique has irreconcilable limitations. Cyclohexene oxide is one of the key starting materials for manufacturing various functional organic compounds and materials such as polymers and chiral organic compounds with cyclohexane moiety [2][3][4][5][6]. Thus, an efficient and fast synthetic

• method for the production of cyclohexene oxide is highly desired to be developed, taking sustainability for the environment and our society into consideration. The general synthetic procedure for cyclohexene oxide is the epoxidation of cyclohexene [7][8]. Among various oxidizing agents used in the

Comparative study of thermally activated delayed fluorescent properties of donor–acceptor and donor–acceptor–donor architectures based on phenoxazine and dibenzo[a,j]phenazine

• Saika Izumi,
• Prasannamani Govindharaj,
• Anna Drewniak,
• Paola Zimmermann Crocomo,
• Satoshi Minakata,
• Leonardo Evaristo de Sousa,
• Piotr de Silva,
• Przemyslaw Data and
• Youhei Takeda

Beilstein J. Org. Chem. 2022, 18, 459–468, doi:10.3762/bjoc.18.48

• (Figure 1) that exhibits efficient orange-to-red TADF [17], and the OLEDs fabricated with POZ-DBPHZ achieved a high EQE up to 16%. However, the role of the number of donors and molecular symmetry in the TADF character of POZ-DBPHZ remained unexplored, due to the lack of a synthetic method to the

• the designed D–A molecule 1, an asymmetric dibenzophenazine electrophile was required. Recently, we have established a synthetic method for such a compound, i.e., 3-trifluoromethanesulfonyldibenzo[a,j]phenazine (DBPHZ-OTf in Scheme 1) to prepare linear-type A–D–A–D compounds [18]. Starting from the

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

• Md Imran Hossain,
• Md Imdadul H. Khan,
• Seong Jong Kim and
• Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

• programs, we decided to optimize the reaction conditions for the synthesis of the trifluoromethyl-substituted isoxazole 3x. We varied the solvent mixtures and the bases, but kept the reaction temperature at room temperature and the reaction time at 2 hours, because these are the highlights of our synthetic

• method. The results are collected in Table 2. First, we varied the proportion of methanol in the solvent mixture with water to increase the solubility of 4,4,4-trifluoro-1-phenyl-1,3-butanedione (2l). As the percentage of methanol in the solvent mixture increased from 5% to 50%, 75%, and 95%, with DIPEA

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

• Martin Vrbický,
• Karel Macek,
• Jaroslav Pochobradský,
• Jan Svoboda,
• Miloš Sedlák and
• Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

• for 26 (R2 = (−)-bornyl, 44–67%). For these findings we do not have any reliable explanation. Next, the synthetic method [12][13] for the preparation of the target oxazolidine-2-one drugs 1 and 2 from the new chiral intermediates was verified (Scheme 2). For this study, the bornyl derivatives 24 and

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• derivatives, the construction of the naphthoquinone ring is also a viable synthetic method to produce menadione. This is a very efficient strategy with great synthetic value, however, it is less used when compared to other methodologies, as it involves more steps and sometimes more complex reactions. One of