Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

• Sebastien Curpanen,
• Per Reichert,
• Gabriele Lupidi,
• Giovanni Poli,
• Julie Oble and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

• , bottom). In spite of extensive experimentation to find better conditions, this result could not be improved. Nevertheless, important information came from an experiment involving furyl carbinol 4c, having a benzyldimethylsilyl unit (Scheme 5). Here, treatment with t-BuOCu⋅LiI in THF/HMPA in the presence

• (as for substrates with pending hydroxy units) [32][33][34][35]. To the best of our knowledge, no analogous cross-coupling reactions from aryl- or heteroaryl-substituted benzyldimethylsilanes have been disclosed. We were thus delighted to find that using Pd2(dba)3 as precatalyst (2.5 mol %) in

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

• Oleg A. Levitskiy,
• Olga I. Aglamazova,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

• % isolated yield, along with some amount of the alkene complex (see Scheme 4). In an attempt to increase the yield of the cysteine derivatives, the amount of the thiol was doubled. Unexpectedly, this resulted in the inversion of the diastereomeric ratio (entry 2 in Table 2). To find a reason, the experiment

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• used to find mass in range (100 to 1000). Computational methods In this work, DFT calculations were used to investigate the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-dione (10ab) from 2-pyrrolidinone (4a/4a’) and methylamine (9b, CH3NH2). The stable structures of reactants, intermediates

Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials

• Valentin H. K. Fell,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Eman J. Hussien and
• Peter J. Skabara

Beilstein J. Org. Chem. 2022, 18, 944–955, doi:10.3762/bjoc.18.94

• triethylamine to the eluent [44]. Also, using a solvent mixture with a low polarity, which is necessary to receive a good separation from the side products, led to a precipitation of the compound on the column, and many attempts were necessary to find an ideal solvent mixture. Additionally, the reaction was

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

• Shao-Cong Zhan,
• Ren-Jie Fang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

• compound 3a (CCDC 2109578) and 4e (CCDC 2109579) were successfully determined by X-ray diffraction. It is pleased to find that the obtained spiro[carbazole-3,5'-pyrimidines] 4a–h have same cis-configuration to that of the above prepared spiro[carbazole-3,3'-indolines] 1a–j and spiro[carbazole-2,3

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• diastereofacial stereoselectivity. Our goal was to identify the nature of transition states associated with two theoretically possible diastereomers and to find out if the experimentally observed diastereomer is more kinetically favorable than the opposite one. The reaction between 3-methyl-3-phenylcyclopropene

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

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

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

• find that the diastereoselectivity of this reaction was not very good. Because the polarity of the two diastereoisomers were very similar, it was very difficult to isolate them as pure compounds by column chromatography. For convenience, only the pure major diastereoisomers of the spiro compounds 3a–w

• expand the scope of this reaction, 3-(ethoxycarbonylmethylene)oxindoles 4 were also employed in the reaction with bis-chalcones 2. We were pleased to find that the reaction proceeded smoothly in the presence of an excess amount of tri(n-butyl)phosphine under similar reaction conditions and the results

• advantages of using readily available substrates, simple operation, good yields, and molecular diversity, which enable it to find potential applications in heterocyclic and medicinal chemistry. Experimental 1. General procedure for the preparation of the spiro[cyclohexane-1,3'-indolines] 3a–w: In an

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

• Jannis A. Reich,
• Miriam Aßmann,
• Kristin Hölting,
• Paul Bubenheim,
• Jürgen Kuballa and
• Andreas Liese

Beilstein J. Org. Chem. 2022, 18, 567–579, doi:10.3762/bjoc.18.59

• heparinus and the aldolase from Escherichia coli K12 were produced in E. coli BL21(DE3). Both enzymes were purified and immobilized on different carriers to find for each enzyme the best choice for a stable and active enzyme preparation when applied under high pressure in continuous operation. For screening

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• -3α,12α,16α-triol (6) [15], 3-epimaslinic acid (7) [18], oleanolic acid (8) [19], and ursolic acid (9) [20]. To find potential antineuroinflammatory, neurotrophic, and cytotoxic secondary metabolites from G. hederacea var. longituba, the isolated compounds (1–9) were evaluated for these biological

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• , we believe this type of biomimetic chiral macrocycles will find more applications as catalysts in other reactions. Design of PKS-inspired multifunctional amino-thiourea macrocycle catalysts. Proposed catalytic mechanism. Synthesis of tetraamino-bisthiourea chiral macrocycles M1–M12. The synthesis of

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

• , and bio-orthogonal chemistry). Our method could also find potential applications in the production of important 3,4,5-trisubstituted isoxazoles, such as the precursors of many β-lactamase-resistant antibiotics like oxacillin, cloxacillin, dicloxacillin, and flucloxacillin (Figure 9), which share a

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

• . Review Preparation methods of menadione Among the most common methods for the preparation of menadione (10), we can find, for example, the oxidation of 2-methylnaphthalene or 2-methylnaphthol. Other less frequent but equally efficient approaches to synthesize menadione include the demethylation of 2

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• ]. In this study, however, two molecules were isolated (1 and 3), the structures of which suggest that the timing of the enzymatic reactions can be interchanged. An alternative explanation would be that compound 5 is metabolized to 1, even though we did not find any literature evidence for such a

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

• Sangram Gore,
• Sundarababu Baskaran and
• Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

• further chemical transformations on the DHPM skeleton. We hope that this environmentally benign one-pot method will find application in the synthesis of 5-unsubstituted dihydropyrimidinones. Biologically active functionalized DHPMs. Synthesis of 5-unsubstituted DHPMs.a Supporting Information Supporting

Trichloroacetic acid fueled practical amine purifications

• Aleena Thomas,
• Baptiste Gasch,
• Enzo Olivieri and
• Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

• operations and waste generation, this methodology should rapidly find applications in organic chemistry laboratories but also possibly on industrial scale. Experimental Typical experimental procedure with dicyclohexylamine 1: Dicyclohexylamine (37 mg, 0.21 mmol, 1 equiv) and 2-methoxynaphthalene (33 mg, 0.21

Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks

• Jolita Bruzgulienė,
• Greta Račkauskienė,
• Aurimas Bieliauskas,
• Vaida Milišiūnaitė,
• Miglė Dagilienė,
• Gita Matulevičiūtė,
• Vytas Martynaitis,
• Sonata Krikštolaitytė,
• Frank A. Sløk and
• Algirdas Šačkus

Beilstein J. Org. Chem. 2022, 18, 102–109, doi:10.3762/bjoc.18.11

• -oxazoles [34][35]. This study aimed to develop and synthesize methyl 5-(cycloaminyl)-1,2-oxazole-4-carboxylates, as new amino acid-like building blocks. This type of functionalized heterocycles could exhibit not only useful biological properties, but also find application as building blocks for the

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

• Jiang-Song Zhai and
• Da-Ming Du

Beilstein J. Org. Chem. 2022, 18, 25–36, doi:10.3762/bjoc.18.3

• room temperature. The results are summarized in Table 1. We were pleased to find that the domino Michael addition/cyclization reaction could complete in the presence of 5 mol % C1 at room temperature in 12 h providing the desired product 3aa in 55% yield with excellent stereoselectivity (>20:1 dr, 97

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• –Miyaura cross-coupling of bromotryptophan-containing peptides of the catenin-binding domain of axin. Optimisation of the linker length in order to find a compromise between both sufficient linker rigidity and flexibility resulted in a peptide with an increased α-helicity and enhanced binding affinity to

• would be speculative to link this property of the P5 to its enhanced biological activity. Instead, we find a more likely reason for the greater activity of P5.2 over that of aAxWt in analysing the conformational diversity of the two peptides (see Supporting Information File 1, Table S2). In P5 trans

A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• noting that N-formyl products are themselves acylating reagents, and thus could find use in photochemical generation of selective acyl donors. Uncaging of peptide backbone N–H bonds from Chan–Lam-type modification. Photocleavage of compounds 1 and 6 under basic conditions. Yield of products was

A tribute to Carsten Schmuck

• Jochen Niemeyer,
• Ivo Piantanida and
• Thomas Schrader

Beilstein J. Org. Chem. 2021, 17, 2795–2798, doi:10.3762/bjoc.17.190

• professors in his group, and I had the pleasure to be one of these (together with Michael Giese and Jens Voskuhl). On top of his support in terms of lab space and finances, Carsten was a great mentor who always managed to find the right balance between kind words of support and words of criticism when

Recent advances in the asymmetric phosphoric acid-catalyzed synthesis of axially chiral compounds

• Alemayehu Gashaw Woldegiorgis and
• Xufeng Lin

Beilstein J. Org. Chem. 2021, 17, 2729–2764, doi:10.3762/bjoc.17.185

• efforts have been made to find new efficient routes for the enantioselective construction of various atropisomeric aryl–aryl or aryl–heteroaryl, enantioselective spiranes and allenes. Despite the advances mentioned above, much of this area of research is still relatively unexplored. Compared to the use of

GlycoBioinformatics

• Kiyoko F. Aoki-Kinoshita,
• Frédérique Lisacek,
• Niclas Karlsson,
• Daniel Kolarich and
• Nicolle H. Packer

Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184

• that important life science questions more often than not include an element of “glyco”. For this thematic issue, we have assembled publications from world-renowned glycoscience researchers who are involved in the current state-of-the-art glycobioinformatics approaches that are needed to find solutions

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

• Dušan Đ. Škorić,
• Olivera R. Klisurić,
• Dimitar S. Jakimov,
• Marija N. Sakač and
• János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

• solubilizers, bile acids are now recognized as metabolism regulators through specific receptors: farnesoid X receptor (FXR) and Takeda G protein receptor 5 (TGR5) [1][2][3]. Research efforts to find ligands for these receptors initiated several synthetic studies where bile acids are being used as a starting

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

• Robin Klintworth,
• Garreth L. Morgans,
• Stefania M. Scalzullo,
• Charles B. de Koning,
• Willem A. L. van Otterlo and
• Joseph P. Michael

Beilstein J. Org. Chem. 2021, 17, 2543–2552, doi:10.3762/bjoc.17.170

• , entry 3). We were pleased to find that heating a solution of 25a in ethanol at 100 °C in a capped microwave tube, but at a much lower power setting (50 W), produced the desired product 26a in 82% yield with little obvious decomposition (Scheme 4). However, the reaction required four hours for the

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• synthesis of functional polymers is also an interesting proposition and such polymers can find promising applications in the organic electronics field such as organic field-effect transistors (OFET) and photovoltaic (PV) cells [15][16]. The synthesis of azulene-containing polymers can be envisaged through