Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

• Viktoria A. Ikonnikova,
• Cristina Cheibas,
• Oscar Gayraud,
• Alexandra E. Bosnidou,
• Nicolas Casaretto,
• Gilles Frison and
• Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169, doi:10.3762/bjoc.20.15

• one-pot transformation from readily available benzyl(prenyl)malonate substrates. After the photooxygenation of the prenyl moiety, the resulting hydroperoxide was directly engaged in a Hock cleavage by adding a Lewis acid. The presence of an aromatic nucleophile in the reaction mixture and that of a

• surrogate readilly unmasked under Hock cleavage conditions. The oxidative cleavage of this alkene would not only release the aldehyde group, but also volatile acetone originated from the traceless isopropylidene motif. Overall, a three-reaction process will thus be performed in one pot (Scheme 1c

• substrates to be submitted to the one-pot tandem transformation (Scheme 5). With only a few exceptions, the presence of ortho (R1), meta (R2), or para (R3) substituents on the benzyl moiety generally allowed the intramolecular Friedel–Crafts reaction, after the first intermolecular one in the presence of

Copper-promoted C5-selective bromination of 8-aminoquinoline amides with alkyl bromides

• Changdong Shao,
• Chen Ma,
• Li Li,
• Jingyi Liu,
• Yanan Shen,
• Chen Chen,
• Qionglin Yang,
• Tianyi Xu,
• Zhengsong Hu,
• Yuhe Kan and
• Tingting Zhang

Beilstein J. Org. Chem. 2024, 20, 155–161, doi:10.3762/bjoc.20.14

• , and aryl bromides as bromination reagents are limited. Wan and Li, respectively, demonstrated a few examples of a one-pot N-acylation and C5–H bromination of 8‑aminoquinolines using acyl bromines acting as both acyl and halide donors [25][26]. The groups of Lei and Fang independently realized the

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• cyclopentadiene moieties. TCBD 4, obtained through the [2 + 2] CA–RE reaction, continues to function as an electron-accepting alkene, as shown in Scheme 4. Subsequent [2 + 2] CA–RE reactions involving electron-rich alkynes yield tetracyano-1,3,5-hexatrienes (TCHTs). These reactions occur seamlessly in a one-pot

• one-pot reaction involving TCNE and one equivalent of 3-(4-(dimethylamino)phenyl)propionitrile in toluene at 90 °C for 24 h. Subsequently, one equivalent of 1 was added at 90 °C for 24 h (Scheme 6) [101]. While the separation of the isomers was not achieved, the structure of the 3Z,5E isomer was

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• , this new method creates two C–N bonds simultaneously based on a mono-halogenated starting material, thus allowing heterocycle formation with diminished halogen waste. Keywords: carbazoles; heteroaromatics; iodanes; metal-catalyzed; one-pot reaction; Introduction N-Acyl carbazoles are effective

• followed by a ring-closure starting from 2,2'-diiodo-1,1'-biphenyls [15][16][17]. Related one-pot procedures are also described (Scheme 1b) [18][19]. Such 2,2´-dihalobiphenyls are established starting materials for synthesizing a variety of heterocycles. Usually, their utilization leads to the production

Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• the PCR assembly step. Because of this, misalignments may occur, and errors may be introduced. (2) PCR assembly of multiple short ODNs in one pot requires similar melting points of the multiple overlapping regions of the short ODNs. Therefore, the sequences of the short ODNs must be carefully chosen

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• NHC·CS2 zwitterions relies on the deprotonation of an azolium salt with a strong base, typically potassium tert-butoxide or potassium bis(trimethylsilyl)amide (also known as potassium hexamethyldisilazide, KHMDS) followed by the addition of carbon disulfide either in one pot or after the isolation of the

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• polyphosphoric acid (PPA) in refluxing chlorobenzene to give 3 (TT) in 86% yield. The brominated TT 4 was obtained through selective monobromination of compound 3 using NBS at −10 °C in DMF in 88% yield. The boronated triphenylamine 6 was constructed in a one-pot two-step reaction in 77% yield, by lithiation of

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

• the construction of various nitrogen-containing polycyclic frameworks (36, 38, 39, 41) (Scheme 17) [32][33][34]. These protocols offered a wide range of substrate compatibility in a one-pot reaction, significantly enhancing synthetic efficiency. Nitrogen-containing heterocycles are abundantly found in

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• -type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products. Keywords: [3 + 2] cycloaddition; decarboxylation; 1,3-dipolar; double cycloaddition; one-pot synthesis; multicomponent reaction; semi

• aldehydes and alkenes. The first cycloaddition products 3c or 3d can also be used as intermediates for other transformations to synthesize novel heterocyclic rings via multicomponent, one-pot, and stepwise synthesis [63][64]. Presented in the following sections is our work on the development of amino acid

• -based decarboxylative [3 + 2] cycloadditions of N–H-type AMYs B3 and B4 for double cycloadditions. The stereochemistry of the cycloadditions and the combination of the cycloaddition with other transformations to be one-pot or stepwise reactions are also presented. Perspective One-step synthesis of

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• notable distinction as they could readily undergo oxidation to yield the corresponding crownphyrins 28–33, incorporating a dipyrrin unit. The synthetic pathway towards crownphyrins is straightforward and relies on a one-pot reaction between diformyldipyrromethane 20a/b and a diamine which introduces the

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• amine protection – can potentially take place in one pot). We have shown that this protocol can be applied to the synthesis of several analogs bearing different substitution patterns on the alkene. The structural diversity that can be readily obtained utilizing this chemistry underscores the versatility

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• Dengxu Qiu Chenhui Jiang Pan Gao Yu Yuan College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.19.113 Abstract Isoxazole derivatives were synthesized via a one-pot method utilizing 2-methylquinoline derivatives as template substrates, sodium

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• previously been shown in the literature that the first two steps of this Smiles-rearrangement approach can be effectively performed in one pot [49]. Therefore, after allowing the O-alkylation to proceed at room temperature in dimethylethyleneurea (DMEU), we proceeded directly to the hydroxyamides 7 and 8

• through the use of additional NaOH and refluxing the crude alkylation mixture. After heating for 3 h, the desired intermediates were recovered in acceptable yields over this two-step one-pot sequence. The amide hydrolysis of 7 and 8 to the desired free naphthylamines 9 and 10 proved challenging, but was

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• the presence of N-(2-bromophenylthio)succinimide 1’ and copper catalyst led to intermolecular sulfenoamination of alkenes and subsequent C–N coupling to produce dihydrobenzothiazine structures 27 in a one-pot manner. Furthermore, deprotection of the amine unit by K2CO3 and Na metal was performed in

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• multifunctional catalytic system 142 incorporating ruthenium nanoparticles (RuNPS) and an NHC–Cu–Cl complex supported on silica (Scheme 56). The catalyst, Ru@SiO2–[Cu(NHC)] was successfully applied to a one-pot tandem A3 reaction of an aldehyde, alkyne, and secondary amine followed by hydrogenation of the

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis

• the Nobel Prize in 2022 to M. Meldal, K. B. Sharpless and C. R. Bertozzi did not come as a surprise. In most cases the (3 + 2) cycloadditions were performed with isolated (and purified) organic azides, but it was early found that one-pot processes generating the potentially hazardous azides [22] in

• was also discussed in a review article [57] dealing with the various types of bis(1,2,3-triazoles). Since we were not interested in compounds such as 4 we did not further investigate details in order to optimize this process. Instead, we looked at the one-pot nucleophilic substitution to generate

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• electrophilic trapping of the intermediary indole anion with alkyl halides provides a concise one-pot synthesis of 3-iodoindoles. The latter are valuable substrates for Suzuki arylations, which are exemplified with the syntheses of four derivatives, some of them are blue emitters in solution and in the solid

• increasingly interesting [26][27]. In addition, as one-pot processes with a huge exploratory potential and diversity-oriented character, syntheses of indoles by multicomponent reactions have aroused considerable interest [28][29][30]. As part of our program to develop heterocycle syntheses based upon

• Discussion In our previous studies on the alkynylation–cyclization synthesis of 2-substituted (aza)indoles [32][33][34], we could show that the copper-free Pd-catalyzed alkynylation of 2-aminobromopyridines or 2-bromoanilines and the subsequent base-catalyzed anellation in a one-pot fashion proceeds without

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

• reacted immediately (one-pot procedure) with sodium borohydride to give 4.4. It must be noted that this sequence does not induce racemization and that 4.4 can be stored for months with 0.5% of solid KOH acting as a stabilizer [72]. Then, 4.4 was alkylated with stearyl tosylate to produce 4.5. The two

• acyl group. Then, the phosphocholine polar head group was introduced with a sequential one-pot procedure using first 2-chloro-2-oxo-1,3,2-dioxaphospholane (12.7) to produce a cyclic phosphate as intermediate that subsequently reacted with trimethylamine to produce thio-PAF 12.8. The opening of

• 22.10. However, the last step features the lower yield (54%) of this 8-step synthesis. In 1994, Bittman et al. reported an alternative strategy to introduce the phosphocholine moiety by the preparation of a cyclic phosphite as a key intermediate [119]. This one-pot three-step sequence starts with the

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• Chandra Sekhar Tekuri Pargat Singh Mahendra Nath Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India 10.3762/bjoc.19.89 Abstract A facile one-pot four-component synthetic methodology is evolved to construct novel copper(II) benzo[f]chromeno[2,3-h

• ; multicomponent synthesis; one-pot reaction; trichloroacetic acid; Introduction π-Conjugated porphyrin macrocycles are known for their applications in numerous areas ranging from oxygen transport, photosynthesis, catalysis and medicine [1][2][3]. In the past several years, diverse organic scaffolds have been

• present study discloses an easy and first synthetic approach to build highly π-conjugated copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins through a trichloroacetic acid-catalyzed one-pot four-component reaction of 2,3-diamino-5,10,15,20-tetraarylporphyrins, 2-hydroxynaphthalene-1,4-dione, aromatic

Retraction: One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

• Mohammad Abbasi and
• Reza Khalifeh

Beilstein J. Org. Chem. 2023, 19, 1170–1170, doi:10.3762/bjoc.19.85

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• Ave., 55a, 644077 Omsk, Russian Federation 10.3762/bjoc.19.83 Abstract An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones

• when irradiated with UV light. Keywords: 5-aminopyrazole; azlactone; elimination; fluorescence; one-pot synthesis; pyrazolo[3,4-b]pyridin-6-one; Introduction The pyrazolo[3,4-b]pyridine scaffold is present in many biologically active compounds [1][2][3][4][5][6][7][8][9][10][11][12]. Among them, 4

• carried out as one-pot synthesis, without isolation of the intermediate dihydro derivative 3а. In this case, the solvent (DMSO) could be added at the stage of obtaining dihydro derivative 3a or introduced into the reaction together with t-BuOK. We have explored both variants. When intermediate 3a was

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• products (e.g., 7) whereas irradiation with blue light (λ = 455 nm) provided disubstituted products 8 (Figure 5A). Additionally, adding a different trapping reagent before switching from green to blue light allows for a sequential and controlled substitution in a one-pot reaction (Figure 5B). 2,4,6

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• hours of reaction. A one-pot method for the synthesis of 1,3-dimethylimidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine 3a was exemplified by successive reactions of imidazo[4,5-e][1,2,4]triazine 7 with diethyl acetylenedicarboxylate and excess KOH. Acidification of aqueous solutions of potassium salts

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

• Elena Y. Mendogralo Maxim G. Uchuskin Perm State University, Bukireva st. 15, Perm, 614990, Russian Federation 10.3762/bjoc.19.74 Abstract A semi-one-pot method for the synthesis of 4-substituted tetrahydrofuro[3,2-c]pyridines by the Pictet–Spengler reaction was developed. The method is based on

• . The reversibility of the acid hydrolysis is quite typical for furans and is more pronounced for di- and polysubstituted furans, due to the higher stability of the latter [49][50][51]. 3-(2-Oxopropyl)piperidin-4-one 5a could be involved into the Paal–Knorr pyrrole synthesis in a one-pot manner. Thus

• methyl iodide (Scheme 5). Conclusion In conclusion, we have developed a semi-one-pot method for the synthesis of 2,3-annulated furans based on the Pictet–Spengler reaction. This method provides a shortcut to 4-substituted tetrahydrofuro[3,2-c]pyridines in reasonable yields starting from readily available

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• -fused tetrahydroquinolines (reaction 1 in Scheme 1) [41][42]. Menéndez and co-workers reported a Yb(OTf)3-mediated Povarov reaction of imines and N-alkyl-1,4-dihydropyridines for the synthesis of hexahydrobenzo[h][1,6]naphthyridines (reaction 2 in Scheme 1) [43]. Khan and co-workers employed a one-pot