Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• each product, but the single crystal X-ray diffraction analysis confirmed the diastereoselectivity of 3. A single crystal of 3g was successfully obtained by slow evaporation of the solvent with the structure unequivocally confirmed by X-ray diffraction analysis (Figure 2). The single crystal X-ray

• diffraction analysis also revealed the presence of four chiral stereocenters with two oxindole moieties at 1,3-possition that are in trans orientation to the 2-benzoyl group and the 5-aryl group is in cis orientation (Figure 2). This observation proved that the most thermodynamically stable diastereomer was

Four bioactive new steroids from the soft coral Lobophytum pauciflorum collected in South China Sea

• Di Zhang,
• Zhe Wang,
• Xiao Han,
• Xiao-Lei Li,
• Zhong-Yu Lu,
• Bei-Bei Dou,
• Wen-Ze Zhang,
• Xu-Li Tang,
• Ping-Lin Li and
• Guo-Qiang Li

Beilstein J. Org. Chem. 2022, 18, 374–380, doi:10.3762/bjoc.18.42

• NOESY correlations of H3-18 with H3-21 suggested the E geometry of Δ17(20). Finally, the absolute configuration of compound 1 was established by single-crystal X-ray diffraction analysis (Figure 4) carried out using Cu Kα radiation with a Flack parameter of 0.0(2). Compound 2, was isolated as a white

• 1.94) with H-14 (δH 1.50) indicated the β-orientation of H-8/H3-18/H3-19, while α-orientation of H-9/H-14. Furthermore, the NOESY correlation of H3-21 with H3-18 suggests the E geometry of ∆17(20). The absolute configuration of 2 was established by single-crystal X-ray diffraction analysis (Figure 4

• the known compound (3β,5α)-25-trihydroxy-24S-methylcholestan-6-one [8]. The difference was the configuration of C-5, which was established as S by single-crystal X-ray diffraction analysis (Figure 4) carried out using Cu Kα radiation with a Flack parameter of −0.11(9). Thus, the absolute configuration

Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines

• Marco Manenti,
• Leonardo Lo Presti,
• Giorgio Molteni and
• Alessandra Silvani

Beilstein J. Org. Chem. 2022, 18, 303–308, doi:10.3762/bjoc.18.34

• diastereoselectivity of the reaction (see Supporting Information File 1). All stereochemical implications were fully confirmed by single-crystal X-ray diffraction analysis, which was performed on well-formed prismatic crystals of compound 2a (Figure 1) [28]. Compound 2a is chiral and crystallizes in the orthorhombic

• determined by single-crystal X-ray diffraction analysis. Conclusion In summary, we have disclosed a reaction protocol that allows efficient homocoupling of oxindole-based N-tert-butanesulfinyl imines and generation of chiral, quaternary 1,2-diamines in a mild and completely stereoselective way. The one-pot

• products we disclosed the efficient homocoupling of oxindole-based N-tert-butanesulfinyl imines, with the generation of chiral, quaternary 1,2-diamines in a mild and completely stereoselective way. The obtained 3,3′-bisoxindole derivatives were fully characterized by NMR and single-crystal X-ray

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

• analysis, 1H, 13C, and 15N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. Keywords: β-enamino ketoesters; heterocyclic amino acids; 15N-labeled 1,2-oxazole; NMR (1H; 13C; 15N); 1,2-oxazole (isoxazole); X-ray structure analysis; Introduction 1,2-Oxazoles (isoxazoles) constitute an

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

• solubility of this substrate. The absolute configuration of the chiral product 3ae was unambiguously identified on the basis of single-crystal X-ray diffraction analysis as (2S,3'S) (Figure 4) [33]. The configurations of the other products were assigned by analogy to 3ae. In order to further prove the

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• (CPE) was investigated using single-crystal X-ray diffraction spectroscopy, isothermal titration calorimetry (ITC) and UV–vis, NMR and IR spectroscopy. The effects of Q[8] on the stability, in vitro release performance and antibacterial activity of CPE were also studied. The results showed that CPE and

• ] and CPE was studied using single-crystal X-ray diffraction, UV–vis and 1H NMR spectroscopy, and the effects of Q[8] on the stability, in vitro release rate and antibacterial activity of CPE were investigated. Results and Discussion The host–guest interaction between Q[8] and CPE Single-crystal

• . Conclusion Herein, the 1:1 host–guest complex of CPE and Q[8] was confirmed using single-crystal X-ray diffraction and 1H NMR, UV–vis and IR spectroscopy. The CPE molecule completely enters the cavity of Q[8] with an inclusion constant of 5.474 × 105 L/mol. The intervention of Q[8] has no effect on the

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• 3e was chosen as a representative compound and its structure was clearly verified by single crystal X-ray diffraction analysis, as shown in Figure 2 (CCDC No. 2104242). Next, the substrate scope of the 1,6-conjugate reaction of TosMIC to p-QMs was examined under optimized conditions (Table 1, entry

Photophysical, photostability, and ROS generation properties of new trifluoromethylated quinoline-phenol Schiff bases

• Inaiá O. Rocha,
• Yuri G. Kappenberg,
• Wilian C. Rosa,
• Clarissa P. Frizzo,
• Nilo Zanatta,
• Marcos A. P. Martins,
• Isadora Tisoco,
• Bernardo A. Iglesias and
• Helio G. Bonacorso

Beilstein J. Org. Chem. 2021, 17, 2799–2811, doi:10.3762/bjoc.17.191

• solution and no signal belonging to the Z isomer was observed in all cases, which can be confirmed by the chemical shift values in the 1H NMR regarding the –CH=N bond. Finally, in order to determine the real molecular structure of the Schiff bases 3, single-crystal X-ray diffraction (SC-XRD) was performed

Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

• Akhil K. Dubey and
• Raghunath Chowdhury

Beilstein J. Org. Chem. 2021, 17, 2642–2649, doi:10.3762/bjoc.17.177

• was found to adopt “(S)” configuration which was unambiguously established by single crystal X-ray diffraction analysis (Figure 1) [45]. To prove the scalability of this synthetic method, we examined the synthesis of 3c and ent-3d in a 1 mmol scale (Scheme 5). The products 3c and ent-3d were isolated

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

• Ivan P. Mosiagin,
• Olesya A. Tomashenko,
• Dar’ya V. Spiridonova,
• Mikhail S. Novikov,
• Sergey P. Tunik and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

• reagents (Scheme 2). Luckily, 4-(2-iodophenyl)pyrrole 2 gave under these conditions target heterocyclic skeleton 3a in 50% yield (Scheme 2). Salt 3a was characterized by 1H, 13C NMR and HRMS, its structure was also confirmed by single-crystal X-ray diffraction analysis (Figure 1). Since iodo-substituted

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• the corresponding γ-carboline products was confirmed unequivocally by single-crystal X-ray diffraction analysis of 3ac (Figure 2). The presence of two substituents in the 1,5-position of indole-2-carbaldehyde substrates such as 1e (5-methoxy-1-methyl-1H-indole-2-carbaldehyde) and 1f (1-methyl-5-phenyl

Structural effects of meso-halogenation on porphyrins

• Keith J. Flanagan,
• Maximilian Paradiz Dominguez,
• Zoi Melissari,
• Hans-Georg Eckhardt,
• René M. Williams,
• Dáire Gibbons,
• Caroline Prior,
• Gemma M. Locke,
• Alina Meindl,
• Aoife A. Ryan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2021, 17, 1149–1170, doi:10.3762/bjoc.17.88

• -crystal X-ray diffraction data were collected on a Bruker APEX 2 DUO CCD, Rigaku CCD, or Bruker D8 Quest ECO diffractometer using graphite-monochromated Mo Kα (λ = 0.71073 Å) and Incoatec IμS Cu Kα (λ = 1.54178 Å) radiation at 100(2), 112(2), and 123(2) K with an Oxford Cryosystems Cobra low-temperature

• Dimé et al. [58]. Crystallography Crystals were grown using techniques following the protocol developed by Hope [59]. Crystals were either grown by allowing the solvent to slowly evaporate over time or by a liquid:liquid diffusion process. The crystal was mounted on a MiTeGen MicroMount and single

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• stereochemistry of these compounds were assigned based on the single-crystal X-ray diffraction analysis of azaspiroheptane 45 with a 9-fenanthryl substituent at 1-position. The same three-step procedure was applied by Reddy and co-workers to synthesize 1-substituted 2,6-diazaspiro[3.3]heptanes 48, starting in

Synthesis, structural characterization, and optical properties of benzo[f]naphtho[2,3-b]phosphoindoles

• Mio Matsumura,
• Takahiro Teramoto,
• Masato Kawakubo,
• Masatoshi Kawahata,
• Yuki Murata,
• Kentaro Yamaguchi,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2021, 17, 671–677, doi:10.3762/bjoc.17.56

• recrystallization. The molecular structure of 2, determined through single-crystal X-ray diffraction analysis, is illustrated in Figure 2, and selected geometrical parameters are shown in Table 1. The results revealed that the naphthalene and fused phosphole rings are almost coplanar (mean deviation = 0.030 Å). The

Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

• Geetanjali S. Sontakke,
• Rahul K. Shukla and
• Chandra M. R. Volla

Beilstein J. Org. Chem. 2021, 17, 485–493, doi:10.3762/bjoc.17.42

• ). Electronically rich Me and OMe groups at the 4- or 6-positions of N-oxides were tolerated and delivered the corresponding C2-triazolylquinolines 3z, 3aa and 3ab in 85–90% yield. Further, the structure was unambiguously confirmed by the single-crystal X-ray diffraction analysis of 3z [63]. Halogenated substrates

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

• Vladislav A. Budevich,
• Sergei V. Voitekhovich,
• Alexander V. Zuraev,
• Vadim E. Matulis,
• Vitaly E. Matulis,
• Alexander S. Lyakhov,
• Ludmila S. Ivashkevich and
• Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

• ) level of theory [42]. X-ray structure determination Single crystal X-ray diffraction data of the mesoionic compounds 8a, 10, 11a, and salt 9 were collected on a SMART Apex II diffractometer using graphite monochromatic Mo Kα radiation (λ = 0.71073 Å) at a temperature of 100 K. The structures were solved

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

• Daria I. Tonkoglazova,
• Anna V. Gulevskaya,
• Konstantin A. Chistyakov and
• Olga I. Askalepova

Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

• -detection (see Supporting Information File 1, Figures S38–S40). X-ray molecular structures The structures of the title compounds 10a–c were further explored by a single-crystal X-ray diffraction analysis (Figure 1, see also Supporting Information File 1, Figures S35–S37 and Table S1) and compared with that

• steps of the method are electrophile-induced 6-endo-dig cyclizations of ortho-alkynylated biaryls. The overall yields of helicenes in five stages of the synthesis exceed 30%. The single-crystal X-ray diffraction analysis revealed the non-planar crystal structures of the synthesized helicenes responsible

Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

• Xinru Sheng,
• Errui Li and
• Feihe Huang

Beilstein J. Org. Chem. 2020, 16, 2954–2959, doi:10.3762/bjoc.16.245

• in the solid state. From single crystal X-ray diffraction, the linear guest molecules thread into cyclic pillar[4]arene[1]quinone host molecules in the solid state, stabilized by CH∙∙∙π interactions and hydrogen bonds. The bromine atoms at the periphery of the guest molecule provide convenience for

• maximum. This also indicated that the interactions between H and G were weak. Conclusion In summary, we constructed novel pseudorotaxanes based on a pillar[4]arene[1]quinone and 1,10-dibromodecane. Single crystal X-ray diffraction analysis showed an alkane molecule threaded into the cavities of two pillar

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• precipitated from the reaction mixture in crystalline form as depicted by scanning electron microscopy (SEM) analysis. The single crystal X-ray diffraction analysis disclosed the arrangement of the α-(arylamino)acetonitrile molecules in the aggregated crystalline state as a racemic mixture. The mutagenic

A heterobimetallic tetrahedron from a linear platinum(II)-bis(acetylide) metalloligand

• Matthias Hardy,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2020, 16, 2701–2708, doi:10.3762/bjoc.16.220

• succeed to obtain single crystals of our metallosupramolecular assemblies that were suitable for single-crystal X-ray diffraction experiments. Therefore, we generated energy-minimized gas phase structures of 4, employing a force-field approach using the GFN2-xTB approach recently established to model

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

• Alexander P. Molchanov,
• Mariia M. Efremova,
• Mariya A. Kryukova and
• Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2020, 16, 2679–2686, doi:10.3762/bjoc.16.218

• ). Accordingly, two characteristic signals for carbon atoms of the pyrazolidine ring are present in the 13C NMR spectrum – at 72.2 (2СН) and 68.7 (СН) ppm. The spatial configuration of the adducts 3e and 3g was further determined by single crystal X-ray diffraction analysis (Figure 1 and Figure 2). All products

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

• Attila Márió Remete,
• Tamás T. Novák,
• Melinda Nonn,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

• (rac)-11b was unequivocally established by single-crystal X-ray diffraction (Figure 1). Then, the preparation of another model compound, the trans-annelated bicyclic carbamide derivative (rac)-13, was attempted. This compound was also unknown in the literature. In the reaction of commercially available

• both NOESY measurements and single-crystal X-ray diffraction (Figure 2 and Figure 3). The next rigid bicyclic system studied was the methyl diendo norbornene dicarboxylate 16. The treatment of 16 with NBS/Deoxo-Fluor® yielded the bromolactone (rac)-17a [37]. The reaction, when repeated only with NBS

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

• Ksenia I. Kaskevich,
• Anastasia A. Babushkina,
• Vladislav V. Gurzhiy,
• Dmitrij M. Egorov,
• Nataly I. Svintsitskaya and
• Albina V. Dogadina

Beilstein J. Org. Chem. 2020, 16, 1947–1954, doi:10.3762/bjoc.16.161

• thiazolopyrimidine-5-ones by reacting 6-methyl-2-thiouracils with bromoethynylketones has been reported by Shishkin and co-workers (Scheme 4) [20]. The authors for the first time proved the structure of the 5-oxo isomer by single crystal X-ray diffraction analysis. The Pd-catalyzed Sonogashira coupling reaction

• those for 3-phenylthiazolo[3,2-a]-5-oxopyrimidine [40]. In addition, the structures of the phosphonylated thiazolopyrimidines 3a and 3d were unambiguously confirmed by single crystal X-ray diffraction data. The presence of the CH3 group at the position 5 of the thiouracil ring changes the reaction

• NMR spectroscopy. In the 13C NMR spectra of the thiazolopyrimidines 6a–c, the O=C–CH=CH fragment is observed by signals of equal intensity at δC 112–113 and 135–136 ppm. However, the unambiguous proof of the structure of thiazolopyrimidine-7-one 6b was obtained by single crystal X-ray diffraction

On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

• Ilya V. Taydakov and
• Mikhail A. Kiskin

Beilstein J. Org. Chem. 2020, 16, 1863–1868, doi:10.3762/bjoc.16.153

• File 1). The structure of acid 12 in solid form was studied by single crystal X-ray diffraction experiments (Figure 3). The structural parameters were deposited at CCDC (deposit No. 1993963, see Supporting Information File 1 for details). Since basic conditions seem to be unsuitable for the hydrolysis

• Supporting Information File 148: Detailed information about experimental procedures, X-ray diffraction experiments for compound 12 and characterization data for compounds 3 and 12. Acknowledgements Single crystal X-ray diffraction analysis was performed using the equipment at the Centre for Collective Use