Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• , Germany), and Avantor Performance Materials (Deventer, Netherlands). An in-house Purelab® flex water purification system (Veolia Water Technologies, Celle, Germany), was used in the preparation of deionized water. Fungal material examined The current study specimen was collected by one of the authors C.D

• comparison of its morphological traits to close relatives. Fermentation and metabolites extraction Mycelial cultures of F. carnea were fermented on solid and liquid-state media based on previously established methodologies [37]. Essentially, the preparation of solid-state media was as follows: 90 mg of rice

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

• ][1,2,4]triazine or imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine and the expansion of the thiazolidine ring to a thiazine core. The methodology proved to be effective for the preparation of a series of target compounds with different substituents in the tricyclic fragment. Examples of natural and

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

• Kasturi U. Nabar,
• Bhalchandra M. Bhanage and
• Sudam G. Dawande

Beilstein J. Org. Chem. 2023, 19, 1008–1014, doi:10.3762/bjoc.19.76

• in oxidation, C–C, C–X bond formation, rearrangements, and halogenation reactions [23][24][25]. Due to the nontoxic nature, easier preparation, and handling of the hypervalent iodine reagents, many researchers are attracted to unravel the chemistry and reactivity of these reagents. Amongst different

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

• act as activated alkene to take part in various cycloaddition reactions [35][36][37][38][39][40]. For example, Lavilla and co-workers developed a Sc(OTf)3-catalyzed three-component reaction of 5,6-unsubstituted 1,4-dihydropyridines, arylamines and ethyl glyoxylate for the preparation of various pyrido

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• temeperatures. In 2000, the application of the Clauson–Kaas reaction was nicely explored by Sonnet et al. [56] for the preparation of diverse pyrrolizinones. The pyrrole derivatives 5 and 7 were synthesized by the classical Clauson–Kaas reaction by refluxing amines 4 or 6 with 2,5-dimethoxytetrahydrofuran (2

• synthesis of arylpyrrolo- and pyrazolopyrrolizinones, in which the Clauson–Kaas reaction was used as key step for the preparation of pyrrole derivatives 13. The condensation of amines 12 with 2,5-DMTHF (2) was carried out in the presence of p-chloropyridine hydrochloride as catalyst and dioxane as reaction

• 2013, Zhang and co-workers [67] reported the preparation of a new recyclable magnetic nanoparticle-supported antimony catalyst (γ-Fe2O3@SiO2-Sb-IL) and its application in the filtration-free, Clauson–Kaas synthesis of N-substituted pyrroles. This catalyst is fairly easy to make, air stable, and

First synthesis of acylated nitrocyclopropanes

• Kento Iwai,
• Rikiya Kamidate,
• Khimiya Wada,
• Haruyasu Asahara and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2023, 19, 892–900, doi:10.3762/bjoc.19.67

• mass spectrometers. All measurements were made on a Rigaku AFC7R diffractometer with graphite monochromatized Mo Kα radiation. Melting points were recorded on an SRS-Optimelt automated melting point system and were uncorrected. Preparation of nitrostyrenes 2 Nitrostyrenes 2 were prepared according to

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• molecular materials, the development of a wide variety of suitable compounds is essential. The use of stimuli-responsive molecules has paved the way for the preparation of advanced functional materials [6][7][8][9][10]. In this scenario, mechanically interlocked molecules (MIMs) have postulated as ideal

• the interlocked arrangement. As an illustrative example, cucurbit[8]uril-based pseudorotaxanes having a pair of styrylpyridinium threads bearing carboxylic acid groups were employed in the preparation of the uranium-organic framework U-CB[8]-MPyVB (Figure 4a) [63]. The solid structure of the MOFs

• deformation paves the way to the development of photoactuator devices leading to envision advanced applications in optomechanics and microrobotics. Outlook The employment of light-responsive rotaxanes and pseudorotaxanes in the preparation of functional advanced materials leads to envision a promising future

A fluorescent probe for detection of Hg²⁺ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

• Xiaoqian Chen,
• Naqin Yang,
• Yue Ma,
• Xinan Yang and
• Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

• ) was purchased from Aladdin, and the other reagents were analytical grade and ready for use. TMeQ[6] was synthesized and purified in our laboratory. Preparation of complex 1 TMeQ[6] (15 mg, 14.26 µmol), ZnCl2 (5 mg, 36.7 μmol) and 1,2-bis(4-pyridyl)ethene (3 mg, 16.48 µmol), were dissolved in 5 mL of 3

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

Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones

• Ksenia Malkova,
• Andrey Bubyrev,
• Stanislav Kalinin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60

• synthesis of quinoline-3-sulfonyl chlorides which are the most common reagents for their preparation. As a possible solution, the approach to the heterocyclic core construction from a sulfonamide-containing building block may be considered. In turn, diversely substituted quinoline-3-sulfones are available

• was predominantly applied for the preparation of the corresponding esters. Inspired by this study, we became interested to utilize o-azidobenzaldehydes 1 in combination with ketosulfonamides/ketosulfones 2 as precursors in a new convenient synthetic procedure leading towards 3-sulfonyl-substituted

• quinolines (sulfonamides and sulfones) (Figure 2b). Herein, we report the successful implementation of this approach. Results and Discussion The Knoevenagel condensation/aza-Wittig reaction cascade was used for the preparation of 3-sulfonyl-substituted quinolines. The process proceeds in a domino fashion

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

• applications in various areas of science and technology [3][4][5]. For example, the use of photoreactions for the preparation of complex natural products allows reducing the number of synthetic steps [6][7][8][9]. Moreover, in some cases photochemical processes can open access to complicated multifunctional

• were not optimal and the process could be significantly improved. In order to employ the aforementioned approach for the preparation of pyrimidines containing an allomaltol moiety we initially selected the interaction of enaminone 13a with cyanamide as a model reaction. We varied time and temperature

• photochemical side processes involving the thiophene ring. Conclusion In summary we have developed an approach for the preparation of pyrimidines with an allomaltol fragment. The suggested method started with the synthesis of pyrimidines from the reaction of 2-(1-(dimethylamino)-3-oxo-3-arylprop-1-en-2-yl)-3

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

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• bandgaps, which significantly enhanced their semiconducting character [4][5]. Hence, the preparation of graphene segments, so-called nanographenes (NGs), has received much attention. In materials science, graphene fragments have been obtained by “cutting” graphene materials through specific chemical

• synthesis started with the preparation of the distorted HBC analogue 49, bearing an aryl iodide for the subsequent Sonogashira cross-coupling reaction with alkyne 50 to give 51. The precursor 116 containing three pre-existing HBCs was synthesized through Co-catalyzed cyclotrimerization of compound 51

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• . Taking into account all these facts, we solved the task of developing a new approach for the synthesis of hybrid molecules containing substituted pharmacophoric heterocyclic and peptidomimetic fragments. An approach based on the preparation of an imidazo[1,2-a]pyridine-containing heterocyclic acid and

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• decrease of the isolated yields. As already demonstrated in our previous work, the Pbf-protected arylglycine products can be directly used as building blocks for peptide synthesis [22]. Finally, we utilized our method for the preparation of a protected version of p-hydroxyphenylglycine (Scheme 5), a common

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• of o-nitrotoluene (22) Reduction to 2,2'-diaminobibenzyl (20) Ring-closing via amine condensation Catalytic dehydrogenation 1.1 Oxidative coupling of o-nitrotoluene (22) and reduction to 2,2'-diaminobibenzyl (20) The preparation of dinitrobibenzyl (21) can be achieved by the oxidative coupling of

• , several methods of carboxamidation were tested, thus allowing the authors to synthesize carbamazepine (CBZ) derivatives of 43. 3 Metal-catalysed cyclisation Diverse metal-catalysed coupling methods exist for the preparation of the dibenzo[b,f]heteropine ring system. The following approaches are broadly

• –Heck coupling Whereas Arnold et al. [30] reported the preparation of dibenzo[b,f]heteropines via consecutive Heck and Buchwald–Hartwig reactions (Scheme 11), amination may also precede the introduction of the double bond (Scheme 17). The formation of the dibenzo[b,f]heteropine skeleton by means of a

Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• developed in the near future for potential biological investigations. On the other hand, various methods have been developed for the synthesis of medium and large phostones and phostines, while only limited strategies have been achieved for the preparation of seven- and eight-membered phostams possibly

• preparation of medium and large phostams, phostones, and phostines. Synthesis of 1,2-azaphosphepine 2-oxide, 1,2-azaphosphocine 2-oxide, 1,2-azaphosphepane 2-oxide, and 1,2-azaphosphocane 2-oxide from ethyl N-allyl-N-(alkenyl(4-phenoxyphenyl)phosphoryl)glycinates. Synthesis of bis[1,2]oxaphosphepine 2-oxide

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• spherical nanoparticles remained relatively stable under different pH conditions. The unique properties of these two fluorescent supramolecular spherical nanoparticles may be valuable for applications in oral drug delivery materials, biomarkers, etc. Experimental Material preparation. Chitosan with a degree

• give CS-TPE as a pale-yellow solid. The CS-TPE obtained with feed ratios (Rf) of 2, 10, and 20 mol % were denominated CS-TPE-2%, CS-TPE-10%, and CS-TPE-20%, respectively. The labelling degree (DL) of CS-TPE was calculated by Equation 1 based on the 1H NMR data. Preparation of TBTQ-C6/CS-TPE

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

• Péter Kisszékelyi and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

• Grédy Kiala Kinkutu,
• Catherine Louis,
• Myriam Roy,
• Juliette Blanchard and
• Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

• of the development of a sustainable chemical industry [1][2][3][4]. Furfurals, which are versatile platform molecules derived from renewable lignocellulose present in agricultural wastes [5][6][7][8], have proven to be of great importance for the preparation of value-added chemicals, biofuels, as

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

• Ita Hajdin,
• Romana Pajkert,
• Mira Keßler,
• Jianlin Han,
• Haibo Mei and
• Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

• closely linked to the substitution pattern of the cyclopropane unit [2]. The prevalence of the biologically active cyclopropyl derivatives, either isolated from natural sources or rationally designed as pharmaceutical agents, has inspired chemists to find efficient methods for their preparation. Among

• (5). This compound was synthesized smoothly within three steps in 16.6% overall yield. The synthetic route commenced from the preparation of N-protected amine 3, followed by the deprotection of benzylamine 3 to furnish 4 and ended with the diazotization of 4 using tert-butyl nitrite. As a result, the

• and aliphatic olefins were examined. The reaction conditions were first optimized using 4-methylstyrene as a model substrate. The results are summarized in Table 1. Initially, dirhodium tetraacetate (Rh2(OAc)4), the most common catalyst for the preparation of cyclopropanes, was applied. To our

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• the success of total synthesis and can be a source of new discoveries. Indeed, as a science allowing the preparation of useful functional compounds, it is strongly connected to biological and medicinal studies, while the development of natural-product-based tools for chemical biology often requires

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• generally there are many different synthetic routes to transition metal/NHC complexes [7][8][9][10][11][12][13][14][15] not all of them are applicable to the preparation of copper(I)/NHC compounds (Scheme 1) [5][6][13][16][17][18][19]. Generally, the so-called direct routes via the appropriate imidazol(in

• “built-in base” route relies on the use of Cu2O which can be directly reacted with a suitable NHC precursor 1 (Scheme 1c) [28]. In any case, the most common approach hinges upon the use of the preliminary preparation of an intermediate silver(I)/NHC complex followed by facile transmetallation to copper(I

• preparation of copper(I)/NHC complexes [45][47]. All mechanochemical syntheses were carried out in a planetary ball mill and the vessel was loaded in an argon-filled glovebox. Copper(I) chloride, imidazolium salt 3 and the appropriate base were mixed (in a molar ratio of 1.0:1.0:1.5, respectively) and ground

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

• Jorge de Lima Neto and
• Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

• route for the preparation of isomeric macrolides of combretastatin D congeners called 11-O-methylcorniculatolide A (5), isocorniculatolide A (7), and 11-O-methylisocorniculatolide A (8), where the key steps comprised an SNAr reaction for the diaryl ether formation and a Mitsunobu reaction for the

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• for preparation. On the other hand, similar methods such as spray-drying do not provide intimate contact between the three types of components for a sufficient period of time to reach the association–dissociation equilibrium [1][27][67]. In this study, the recovery yields were in the range of 51.5