Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN

• Jialiang Wu,
• Haofeng Shi,
• Xuemin Li,
• Jiaxin He,
• Chen Zhang,
• Fengxia Sun and
• Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

• investigate the effects of different substituents R2 and R3. When the methyl substituent (R2) was replaced with an aryl group, the corresponding thiocyanated products 2l–o could be obtained in acceptable to moderate yields. On the other hand, the method was equally applicable to the substrate bearing two aryl

• selenocyanated products 3a–o achieved in acceptable to good yields. Similarly, the selenocyanation of C3- and C5-unsubstituted substrate 1p regioselectively furnished the 4-selenocyanated pyrazole 3p in good yield. The utility of this approach was further demonstrated by a scale-up experiment. When 10.0 mmol of

Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation

• Md Azadur Rahman,
• Hirofumi Endo,
• Takashi Yamamoto,
• Shoma Okushiba,
• Norihiko Sasaki and
• Toshiki Nokami

Beilstein J. Org. Chem. 2024, 20, 1421–1427, doi:10.3762/bjoc.20.124

• linear trisaccharide 20b were produced with monomer 17b with a 3,4-di-O-benzyl group (Table 2, entry 2). Although the 3-hydroxy protecting group R3 also affected the product distribution, formation of the corresponding 1,6-anhydrosugars was not observed in both cases. NMR data suggested that cyclic

Challenge N- versus O-six-membered annulation: FeCl₃-catalyzed synthesis of heterocyclic N,O-aminals

• Giacomo Mari,
• Lucia De Crescentini,
• Gianfranco Favi,
• Fabio Mantellini,
• Diego Olivieri and
• Stefania Santeusanio

Beilstein J. Org. Chem. 2024, 20, 1412–1420, doi:10.3762/bjoc.20.123

• Abstract A new class of heterocyclic N,O-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin

• intermediates through selective FeCl3-catalyzed intramolecular N-annulation. Keywords: α-aminoacetals; fused-ring systems; heterocyclic hemiaminals; heterocyclic N,O-aminals; multicomponent reactions; Introduction N-Fused heterocycles are ubiquitous within crucial molecules, including biologically active

• to afford, by a chemospecific Lewis acid-catalyzed ring-closure protocol, valuable heterocyclic N,O-aminals (Scheme 1). Results and Discussion Since the direct functionalization of N-heterocycles offers an attractive entry to important molecular targets that might otherwise require lengthy synthetic

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

• Akanksha Chhikara,
• Fan Wu,
• Navdeep Kaur,
• Prabagar Baskaran,
• Alex M. Nguyen,
• Zhichang Yin,
• Anthony H. Pham and
• Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

• desired oxazoline products with reasonable yields (Figure 2, products 8–10). Heteroaromatic amides could also furnish the oxazolines 11 and 12 with good efficiency. Naphthaleneamide also generated the desired product 13, albeit with slightly lower efficiency. Interestingly, o- and m-methyl-substituted

• , ester, and phthalimide proceeded smoothly with good yields and excellent regioselectivities to access the oxazoline products as single regioisomers (Figure 3, products 18–22). The o-bromo-substituted styrene also afforded the corresponding product 23. Furthermore, 1,1-di-substituted α-methylstyrene and

• Conversion of Chemical Feedstock to O- and N-Containing Heterocycles”. Funding We thank the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R15GM139156 for supporting this work. We thank the University of Toledo for an internal seed grant from the Summer

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• phthalides 100, as evidenced by the per-O-methylated derivative of pestalone, a marine natural substance. Either in a Cannizarro–Tishchenko-type reaction with nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm), the transformation often proceeds without any problems in DMSO (Scheme

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

• Mithu Roy,
• Bitan Sardar,
• Itu Mallick and
• Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

• radicals by activation of C–O bonds using visible-light photoredox catalysis offers a mild and environmentally benign approach to useful chemical transformations. Alcohols, carboxylic acids, anhydrides, xanthates, oxalates, N-phthalimides, and thiocarbonates are some examples of alkyl and acyl precursors

• that can produce reactive radicals by homolysis of the C–O bond. These radicals can then go through a variety of transformations that are beneficial for the construction of synthetic materials that are otherwise difficult to access. This study summarizes current developments in the use of organic

• photocatalytic and electrochemical deoxygenation of acids and alcohols has attracted significant attention as the strategic cleavage of the C–O bond is quite challenging and opens up new possibilities for constructing useful compounds [12][13][14]. The use of photogenerated carbon-centered radicals, such as acyl

Rhodium-catalyzed homo-coupling reaction of aryl Grignard reagents and its application for the synthesis of an integrin inhibitor

• Kazuyuki Sato,
• Satoki Teranishi,
• Atsushi Sakaue,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai,
• Hiroyuki Takeda,
• Tatsuo Kinashi and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118

• amount of 3,3''-difluoro-1,1':3',1''-terphenyl (6h) as side product, that might derive from an SNAr reaction of 3h with the Grignard reagent of 5h. Moreover, bromoxylenes 5m–o also gave the corresponding products 3m–o, respectively, although the position of substituents affected the yields. On the other

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• a valuable recyclization of various systems containing an N–O bond in the ring. This approach is a powerful synthetic tool allowing to obtain diverse types of nitrogen-containing five-membered heterocycles [1][2]. Among the wide variety of recyclizations of this class the processes with

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• results were not fully satisfactory. Considering the poor solubility of fullerene derivatives, toluene, carbon disulfide (CS2), and ortho-dichlorobenzene (o-DCB) were tested as solvent. Surprisingly, the conversion from ketone to thioketone did not occur as anticipated. In another attempt, where the

• around 1000 cm−1 for t-Bu-FIDS. Ultraviolet–visible (UV–vis) spectroscopy of t-Bu-FIDS in o-DCB exhibited two prominent UV absorption bands with peaks at 257 nm and 320 nm (Figure 1b). The absorption at 257 nm indicated the integrity of the fullerene cage chromophore. The absorption peak at 320 nm was

• assigned to the charge transfer band of the C=S bond in t-Bu-FIDS, which was stronger than that of the C=O bond in t-Bu-FIDO [30]. Interestingly, the maximum absorption band observed in t-Bu-FIDO at 432 nm, which is a characteristic feature of 58π-fullerene derivatives with a 1,2-addition pattern, was

Domino reactions of chromones with activated carbonyl compounds

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1256–1269, doi:10.3762/bjoc.20.108

• ) [40]. The formation of the products can be explained by 1,4-addition of the terminal carbon of the diene to the chromone to give intermediate O and subsequent attack of the central carbon atom of the 1,3-dicarbonyl unit (aldol reaction). No aromatization and extrusion of the hydroxy group was observed

• ). Acknowledgements I am grateful to my co-workers who contributed to the work included in this account article. These are (in alphabetical order): Drs Uwe Albrecht, Bettina Appel, Alina Bunescu, Friedrich Erben, Edith Holtz, Muhammad Farooq Ibad, Ilia Freifeld, Viktor O. Iaroshenko, Abid Obaid-ur-Rahman, Muhammad A

Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide

• Vishnu Selladurai and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2024, 20, 1221–1235, doi:10.3762/bjoc.20.105

• Vishnu Selladurai Selvakumar Karuthapandi Department of Chemistry, School of Advanced Sciences, VIT-AP University, Amaravati-522237, Andhra Pradesh, India 10.3762/bjoc.20.105 Abstract This article describes the detailed analysis of the reaction between arylamines, such as aniline, o-anisidine

• polymerization, and solvent oxidation. For aniline and o-anisidine, predominant oxidative polymerization occurred, leading to the formation of the respective polyaniline polymers as major products. For methyl anthranilate, the oxidative polymerization was suppressed due to the delocalization of amine lone pair

• [30][31][32]. Due to the oxidative nature, the use as selenium source in the synthesis of arylchalcogen compounds, in particular diorganyl selenides, can be a challenging process that involves sequential formation of two C–Se bonds and reduction of a Se=O bond in a single-pot reaction. Further

Cofactor-independent C–C bond cleavage reactions catalyzed by the AlpJ family of oxygenases in atypical angucycline biosynthesis

• Jinmin Gao,
• Liyuan Li,
• Shijie Shen,
• Guomin Ai,
• Bin Wang,
• Fang Guo,
• Tongjian Yang,
• Hui Han,
• Zhengren Xu,
• Guohui Pan and
• Keqiang Fan

Beilstein J. Org. Chem. 2024, 20, 1198–1206, doi:10.3762/bjoc.20.102

• contraction reactions, yielding a benzofluorene intermediate 4 and the dimer 5, both featuring a kinamycin skeleton (Scheme 1) [11][12]. Recent investigations unveiled the catalytic activity of the O-methyltransferase-like protein AlpH, which catalyzes a unique SAM-independent coupling of ʟ-glutamylhydrazine

Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol

• Naziha Tarannam,
• Prashant Kumar Gupta,
• Shani Zev and
• Dan Thomas Major

Beilstein J. Org. Chem. 2024, 20, 1189–1197, doi:10.3762/bjoc.20.101

• (GPP, FPP, GGPP) undergo highly complex cyclisation cascades forming terpenes and terpenoids that often have great structural complexity. For class I terpene synthases this multistep process is initiated by a heterolytic C–O bond cleavage, separating the diphosphate and isoprenoid ion pairs [3][4]. The

• stability trend between F-OH and H-OH. The second order perturbation energy (E(2)) value for O(LP) to C(LV) (LP = lone pair, LV = lone valence orbitals) charge transfer in F-OH is 2.9 kcal/mol, whereas there is no such charge transfer in H-OH. This explains the relative stability of F-OH compared to H-OH

• between the stability of hedycaryols (ΔΔEe) and C+···OH bond distances. Biosynthesis of (A) germacrene A and (B) hedycaryol from FPP. Here the abbreviations represent, FPP = farnesyl diphosphate, GAS = germacrene A synthase, OPP = diphosphate. O–C(cation) bond lengths (Å) in the hedycaryol cations

Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• calculated respectively for C60, 2, and 3. Experimental Materials and general method: All chemicals were reagent grade, purchased from commercial suppliers. o-Dichlorobenzene (ODCB) was distilled from P2O5 under vacuum before use. Toluene was distilled from benzophenone sodium ketyl under dry N2 prior to use

• ) level. Hydrogen atoms are omitted for clarity. Cyclic voltammograms (CV) and differential pulse voltammograms (DPV) of 3 in o-dichlorobenzene containing 0.1 M (n-Bu)4NPF6. In DPVs, peaks of the adducts are denoted by circles. Potentials are shown in volts relative to the ferrocene/ferrocenium couple

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• dehydrogenation of alcohol-yielding Mn18-b species. Mn–H complex reduced the C=C and C=O bonds, yielding the fully reduced saturated alcohol products (Scheme 44). In 2019, the upgrading of bio-derived ethanol with widely available methanol for the production of isobutanol was developed by Liu and co-workers using

• hydrogenated the C=C and C=O bonds delivering the desired alkylated alcohol products (Scheme 49). Recently, Maji’s group showed environmentally benign examples of the manganese-catalyzed dehydrogenative coupling of ethylene glycol and primary alcohols producing value-added α-hydroxycarboxylic acid molecules

Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

• Maksim V. Kvach,
• Stefan Harjes,
• Harikrishnan M. Kurup,
• Geoffrey B. Jameson,
• Elena Harjes and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

• anomers with a α/β ratio of 2:1, as determined by 1H and 13C NMR. Deprotected nucleosides Va and Vb but not Vc exhibited absorbance in the UV region with ε258 = 4230 L⋅mol−1⋅cm−1 and ε262 = 4730 L⋅mol−1⋅cm−1, respectively. This was most likely a result of the presence of a double bond next to the P=O unit

• in nucleosides Va and Vb, whereas there is no double bond in the nucleobase of compound Vc. For incorporation of nucleoside Va into DNA, it needed to be equipped with standard 5'-O-DMT and 3'-O-N,N-diisopropylamino-2-cyanoethoxyphosphanyl groups. Further, the negative charge on the nucleobase needed

• to be eliminated as it might otherwise interfere with automated DNA synthesis. Starting from compound 14 as a mixture of anomers, compound Va was obtained using above described steps, and after installation of a 5'-O-DMT group, individual anomers of 21 were isolated on reversed-phase column (C18

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• the synthesis of aryl-cored polybromides obtainable from xylenes or mesitylene. The selected targets are those of heightened interest to the scientific community, identified as those with a score of at least 100 reaction hits in the Scifinder® search (Figure 3). Results and Discussion As p- and o

• undetectable 1H NMR impurities. The application of the same protocol on o-xylene (1, Figure 3) cleanly gave dibromide 1a in almost quantitative yield. Some issues emerged during the isolation step, because of the high lacrimatory activity of 1a [53][54], while 3a lacks the same effect. Higher nucleophilic

• aromatic cores are affected by minor, yet inevitable, bromination on the ring. This is the case of dialkyl-substituted arenes having o,p-activated positions (ortho with respect to one alkyl substituent and para with respect to another alkyl substituent). For instance, bromination of m-xylene (2, Figure 3

Novel route to enhance the thermo-optical performance of bicyclic diene photoswitches for solar thermal batteries

• Akanksha Ashok Sangolkar,
• Rama Krishna Kadiyam and
• Ravinder Pawar

Beilstein J. Org. Chem. 2024, 20, 1053–1068, doi:10.3762/bjoc.20.93

• largest for systems whose unsaturated bridge was extended with –CH2–, –NH–, and –O– units. Interestingly, these TBR barriers for the studied BBD-based photoswitches with elongated unsaturated bridges are substantially higher and can store the energy for several months and even longer. Overall, the studied

• of the BBD molecule relieves strain in the metastable photoisomer and thus, enhances the TBR barrier. The calculated energy barrier of TBR was found to be largest for the systems whose unsaturated bridge was extended with –CH2–, –NH–, and –O– units. Therefore, it is worth to mention that elongating

• unsaturated bridge of the bicyclic diene. The energetic stability of the undesired byproduct is lowest for the photoswitching system whose bridge length is elongated with –(CO)– and –CH2– units followed by –NH– and –O– units. The calculated energy difference between the parent diene and the competing

Structure–property relationships in dicyanopyrazinoquinoxalines and their hydrogen-bonding-capable dihydropyrazinoquinoxalinedione derivatives

• Tural N. Akhmedov,
• Ajeet Kumar,
• Daken J. Starkenburg,
• Kyle J. Chesney,
• Khalil A. Abboud,
• Novruz G. Akhmedov,
• Jiangeng Xue and
• Ronald K. Castellano

Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92

• Yamashita’s DCPQs 1a (BenzCN) and 2a (XyICN) began via SNAr reaction of commercially available o-phenylenediamines 11a and 11b with building block 13 to afford dihydropyrazine derivatives 8 and 9, respectively, as precipitates in 1,4-dioxane solution. The reaction generates two equivalents of HCl, adding a

• secured due to the favorable hydrogen bonding (O–H∙∙∙N) between the oxime units; this idea is supported by 1H NMR spectroscopy which shows the presence of two distinct hydroxyl proton signals. The reduction of 7d in the presence of Pd/C and hydrazine monohydrate afforded 1,10-phenanthroline-5,6-diamine

• respect to the carbonyl groups (Figure 6b) and 5.25° concerning peripheral rings 1 and 3 (Figure 6c). The unit cell is composed of a dimer of 2b held together by intermolecular N–H∙∙∙N and C–H∙∙∙O=C H-bonds with average distances of 2.30 Å and 2.28 Å, respectively (Figure 6d and 6e). The herringbone

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• modifying their physical properties, and stability and controlling the reactivity of arylation processes, as demonstrated in various studies [9][10]. For instance, the Gaunt group reported that the use of a fluoride counterion in diaryliodonium(III) salt can trigger phenol O-arylation by activating the

• phenolic O–H group with a fluoride anion [11]. Additionally, Muñiz et al. found that the acetate counterion was more effective than chloride, hexafluorophosphate, and trifluoromethane sulfonate for the borylation of diaryliodonium(III) salts [12]. Recently, our group has developed a new method for phenol O

• increase in temperature facilitates the ligand coupling between the phenyl group and the carboxylate counterion. When heated at 140 °C for 2.5 h under solvent-free conditions, iodonium salt 7aa underwent carboxylate O-phenylation with complete phenyl group transfer, resulting in the formation of phenyl

Spin and charge interactions between nanographene host and ferrocene

• Akira Suzuki,
• Yuya Miyake,
• Ryoga Shibata and
• Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

• . The elemental abundance ratio O/C of 0.07 is the same for ACFs and FeCp2-ACFs-150, similar to the carbon atoms ratio at the nanographene's edge part with the in-plane size of 2–3 nm, where the ratio of edge atoms to total carbon atoms is ca. 0.1 with the assumption of a model circular nanographene

• C324H36. Thus, oxygen-containing functional groups in ACFs are mainly attached to the edge part of nanographene, being consistent with the higher chemical activity of the edges of graphene [2][6]. Furthermore, the almost same elemental abundance ratio O/C between ACFs and FeCp2-ACFs-150 indicates no

• –O, C=O), shake-up peak by π–π* transition of conduction π electrons (Shake-up) [28]. A more considerable contribution of the plasmon peak in C1s indicates an increase in π-electron carriers for FeCp2-ACFs-150. Indeed, the shift of the C=C peak of FeCp2-ACFs-150 to the lower energy side indicates an

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

• , Davies et al. published a paper presenting a new method for the synthesis of indoles from o-nitrostyrenes by using a different catalyst system and performing the reaction under mild conditions [27]. At first they decided to change the catalytic system applied by Söderberg using 1,10-phen instead of PPh3

• as ligand, because it was already known that catalysts derived from palladium(II) salts and bidentate nitrogen ligands were highly reactive systems for the reduction of o-nitrostyrenes [28][29][30]. The catalytic system Pd(OAc)2/1,10-phen worked better than Söderberg´s one (Pd(OAc)2/PPh3) under mild

• palladium-catalyzed transformation of o-vinylnitrobenzenes and o-nitrostilbenes with carbon monoxide as the reductant to give indoles after cyclization [37]. In the presence of 1–2 mol % of Pd(OAc)2, 1,10-phen (4 mol %) and tributylamine (40 mol %), the desired products were formed in good to excellent

Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

• Arnaldo G. de Oliveira Jr.,
• Martí F. Wang,
• Rafaela C. Carmona,
• Danilo M. Lustosa,
• Sergei A. Gorbatov and
• Carlos R. D. Correia

Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84

• Heck adducts (methyl N,O-acetals) were efficiently converted into several arylated γ-lactams by a simple oxidation procedure (Jones oxidation). To demonstrate the applicability of the strategy, two of the chiral aryl-lactams were further derivatized to provide the selective phosphodiesterase-4

• presence of a methoxy group after the Heck–Matsuda reaction indicates methanolysis after arylation. Given the importance of the lactam rings, we envisioned a sequential Jones oxidation protocol without isolation of the methyl N,O-acetal products to obtain the corresponding lactams 4. As observed in

• 4bo (o-phenoxy and o-bromo group, respectively), the er dropped considerably. Finally, a strong electron-withdrawing group in the ortho position such as nitro (4bn) was met with a decrease in yield (66%), but with a higher er. During the development of the scope, the hemiaminal ethers (Heck–Matsuda

Monitoring carbohydrate 3D structure quality with the Privateer database

• Jordan S. Dialpuri,
• Haroldas Bagdonas,
• Lucy C. Schofield,
• Phuong Thao Pham,
• Lou Holland and
• Jon Agirre

Beilstein J. Org. Chem. 2024, 20, 931–939, doi:10.3762/bjoc.20.83

• validation report is the beginning of the carbohydrate information, listed as ‘glycans’ in the JSON format. Within this ‘glycan’ scope, information is segmented into glycan types, that is, ‘n-glycan’, ‘o-glycan’, ‘s-glycan’, ‘c-glycan’, and 'ligand'. Each of these glycan types contains an array of individual

• interface on the Privateer database homepage, carbohydrate-containing PDB entries can easily be found and filtered. Privateer database entries for specific glycosylation types, namely, N-glycosylation, O-glycosylation, S-glycosylation, or C-glycosylation can be filtered quickly and easily. Additional

• total deposited models into the PDB for all structural determination methods. Lines show glycosylation in the PDB over time, split into N-glycans, O-glycans, S-glycans, and C-glycans. Data contained within each glycan entry. Data contained within each sugar entry. Data contained within each linkage

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline

• Jiawei Niu,
• Yuhui Wang,
• Shenghu Yan,
• Yue Zhang,
• Xiaoming Ma,
• Qiang Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2024, 20, 912–920, doi:10.3762/bjoc.20.81

• ., PCy3 and P(o-tol)3 reduced the yield of the desired product 6a (Table 1, entries 7 and 8). Lowering the amount of Pd(OAc)2 or changing the reaction temperatures resulted low yields of 6a (Table 1, entries 9–11). Similar results were observed from the reactions using other bases, such as K3PO4, NaOAc