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Search for "one-pot" in Full Text gives 755 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

From amines to (form)amides: a simple and successful mechanochemical approach

  • Federico Casti,
  • Rita Mocci and
  • Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

Graphical Abstract
  • ]. In this work, we aimed to set compatible conditions to access formamides, envisioning the possibility of generating the isocyanide in a one-pot, two-step reaction. However, to the best of our knowledge, despite the notable improvement in the mechanochemical synthesis of the amide moiety [44][48][49
  • compatible means in the view of a one-pot methodology for preparing isocyanides directly from amines [56]. When the amine 1 was reacted in the presence of Et3N, HCOOH, and p-Ts-Im [58] (Table 1, entry 5), the formamide was accompanied by a significant amount of sulfonamide (formamide/sulfonamide ratio: 70:30
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Published 12 Sep 2022

Derivatives of benzo-1,4-thiazine-3-carboxylic acid and the corresponding amino acid conjugates

  • Péter Kisszékelyi,
  • Tibor Peňaška,
  • Klára Stankovianska,
  • Mária Mečiarová and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 1195–1202, doi:10.3762/bjoc.18.124

Graphical Abstract
  • significantly accelerated by ultrasonic irradiation [16]. Cyclocondensation of 1,3-dicarbonyl compounds with substituted diaryl disulfides in water in the presence of β-cyclodextrin gave 2,3-disubstituted benzo-1,4-thiazines in 70–91% yield in 50 min [17]. A highly efficient visible-light-mediated one-pot
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Published 09 Sep 2022

Lewis acid-catalyzed Pudovik reaction–phospha-Brook rearrangement sequence to access phosphoric esters

  • Jin Yang,
  • Dang-Wei Qian and
  • Shang-Dong Yang

Beilstein J. Org. Chem. 2022, 18, 1188–1194, doi:10.3762/bjoc.18.123

Graphical Abstract
  • recognized as challenging since there is no single report on such a sequence under Lewis acid catalysis. Herein, we report the synthesis of phosphoric esters by a Lewis acid Cu(OTf)2-catalyzed one-pot Pudovik reaction–phospha-Brook rearrangement sequence between pyridinyl-substituted aldehyde or pyridone
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Published 09 Sep 2022

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

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  • acids. One-pot combination of the reductive ring opening and subsequent addition of thiols allows obtaining the cysteine derivatives in practical yields and with high stereoselectivity at the removed β-stereocenter. Keywords: amino acids; cathodic cyclopropane opening; cysteine derivatives; Ni–Schiff
  • reactions with electrophiles, intramolecular cyclization and disproportionation process. The synthetic viability of the approach will be considered. A one-pot multistep synthetic protocol is suggested, based on addition of thiols to the mixture of isomeric alkenes formed in an electroreductive opening of a
  • that follow-up functionalization of the anions formed after the ring opening with electrophiles (except H+) has low synthetic value due to multiple competing reaction channels observed in case of 3 and decreased nucleophilicity of 4. Consequently, it seems reasonable to focus on the one-pot
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Published 08 Sep 2022

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

  • Md Azadur Rahman,
  • Kana Kuroda,
  • Hirofumi Endo,
  • Norihiko Sasaki,
  • Tomoaki Hamada,
  • Hiraku Sakai and
  • Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

Graphical Abstract
  • blocks can reduce the number of steps in the total synthesis. However, it requires manipulation of the anomeric leaving groups and deprotection of the protected hydroxy group at the 4-position prior to glycosylation. Although automated electrochemical assembly, which is a one-pot iterative synthesis of
  • examined. By repeating cycles in one pot, the modified method enabled us to prepare longer oligosaccharides up to the octasaccharide. Further optimizations of reaction parameters, such as concentration, size and shape of electrodes for large-scale production of oligosaccharides, and deprotection of
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Published 30 Aug 2022

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

  • Yara Cristina Marchioro Barbosa,
  • Guilherme Caneppele Paveglio,
  • Claudio Martin Pereira de Pereira,
  • Sidnei Moura,
  • Cristiane Storck Schwalm,
  • Gleison Antonio Casagrande and
  • Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

Graphical Abstract
  • ligand (Table 1, entry 22), but the product could not be detected by TLC analysis. In order to compare the efficiency of the optimized conditions with the one-pot approach, a reaction was carried out starting from o-chlorobenzaldehyde and phenylhydrazine under the conditions shown in Table 1, entry 3
  • , hexane/AcOEt 80:20 for 4g, hexane/AcOEt 98:2 for 4h, and hexane/AcOEt 85:15 for 4i and 4i’. One-pot approach for the synthesis of 2a. aYield calculated vs trichloroethylene by 1H NMR spectroscopy. Regioselectivity of the reaction of arylhydrazones 1i and 3i, respectively. Optimization of the reaction
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Published 23 Aug 2022

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system

  • Lin Chen,
  • Xuan Zhou,
  • Zhiyong Chen,
  • Changxu Wang,
  • Shunjie Wang and
  • Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

Graphical Abstract
  • Lin Chen Xuan Zhou Zhiyong Chen Changxu Wang Shunjie Wang Hanbing Teng School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 122 Luoshi Road, Wuhan, 430070, China 10.3762/bjoc.18.104 Abstract An economical and versatile protocol for the one-pot synthesis of
  • . In the whole process, no extra carbon was introduced. Conclusion In conclusion, we have developed an economical and versatile protocol for the one-pot synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system. This work further extends the application of
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Published 17 Aug 2022

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

  • Mio Matsumura,
  • Kaho Tsukada,
  • Kiwa Sugimoto,
  • Yuki Murata and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

Graphical Abstract
  • their applications in the biological and pharmaceutical fields. The Cu-catalyzed tandem reaction for the synthesis of novel alkynyl imidazopyridinyl selenides is presented. A one-pot synthesis route afforded alkynyl imidazopyridinyl selenides in moderate to good yields. This was achieved by a two-step
  • reaction between terminal alkynes and diimidazopyridinyl diselenides, generated from imidazo[1,2-a]pyridines and Se powder, using 10 mol % of CuI and 1,10-phenanthroline as the catalytic system under aerobic conditions. The C(sp2)–Se and C(sp)–Se bond-formation reaction can be performed in one-pot by using
  • attention [15][19][20][21][22][23][24][25][26]. This method involves a transition-metal-catalyzed one-pot, three-component reaction in which two functional groups are simultaneously introduced on the Se atom via double selenation. As examples, the following Cu-catalyzed one-pot reactions have been reported
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Published 19 Jul 2022

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

Graphical Abstract
  • underwent a [4 + 2] cycloaddition reaction (reaction 1 in Scheme 1) [69][70][71][72][73][74]. This metal-catalyzed one-pot reaction not only combined the advantages of a traditional Diels–Alder reaction and the recently developed multicomponent reactions, but also meets the goal of green and sustainable
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Published 07 Jul 2022

New synthesis of a late-stage tetracyclic key intermediate of lumateperone

  • Mátyás Milen,
  • Bálint Nyulasi,
  • Tamás Nagy,
  • Gyula Simig and
  • Balázs Volk

Beilstein J. Org. Chem. 2022, 18, 653–659, doi:10.3762/bjoc.18.66

Graphical Abstract
  • in various ways (we only show here the path that seems the most advantageous). According to this, compound 17 was N-alkylated at the indoline nitrogen atom with N-methylchloroacetamide to give 18, then cyclized in one pot to derivative 8. Alternate methods for the 17→8 transformation require more
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Published 10 Jun 2022

DDQ in mechanochemical C–N coupling reactions

  • Shyamal Kanti Bera,
  • Rosalin Bhanja and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

Graphical Abstract
  • the presence of DDQ, the intramolecular C(sp2)–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in high yields
  • ten innovative technologies that IUPAC recognized [7]. To perform organic transformations in a greener way, the mechanochemical methods can also be considered as one of the alternative approaches [8][9][10]. The one-pot multicomponent synthesis of important heterocycles can be the state of art
  • toward the synthesis of 1,2-disubstituted benzimidazoles [39] under mechanochemical (ball milling) conditions (Figure 1a). In addition, the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes in the presence of DDQ resulted in substituted quinazolin-4(3H)-one [40] derivatives (Figure 1b
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Published 01 Jun 2022

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

  • Prodip Howlader and
  • Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

Graphical Abstract
  • advantages of utilizing self-assembly to construct discrete nanocages with predetermined geometry and function is the use of a one-pot reaction employing complementary organic linkers with inorganic metal ions. Although the one-pot synthesis of homoleptic metallacages has been thoroughly investigated over
  • -bonding, which would lead to catalytic quenching, a unique design strategy was applied. Instead of using a cis-blocked palladium(II) unit for self-assembly, Pd(NO3)2 was employed along with the triazole-based 0° clip 13. In a one-pot reaction, 12 and 13 in DMSO were treated with Pd(NO3)2 in a 1:1:1 ratio
  • solvents restricts their use in potential applications. In this aspect, coordination-driven discrete architectures provide a promising future due to their facile one-pot synthesis and high solubility in common solvents. Mukherjee and co-workers have developed supramolecular architectures containing
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Published 27 May 2022

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

  • Masayori Hagimori,
  • Tatsusada Yoshida,
  • Yasuhisa Nishimura,
  • Yukiko Ogawa and
  • Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

Graphical Abstract
  • . pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines 3a,b and N-methyl-4-((pyridin-2-yl)amino)maleimides 4a–e, were selectively prepared by a one-pot reaction between a functionalized maleimide and 2-aminopyridines with electron-donating or electron-withdrawing groups at position 5 and were investigated
  • the electronic nature of the compounds with and without AIEE properties. Keywords: acceptor–donor–acceptor; AIEE; low molecular weight; one-pot reaction; ((pyridin-2-yl)amino)maleimide; TD-DFT calculation; Introduction Fluorescent compounds have attracted considerable attention as functional
  • study, we used 1-methyl-4-(methylsulfanyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (1) with a methylsulfanyl group as a good leaving group. As shown in Scheme 1, the one-pot reaction of 1 with 2-aminopyridine (2a) proceeded by refluxing in ethanol for 2 h to produce the ring-fused pyridine
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Published 24 May 2022

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

Graphical Abstract
  • and operational simplicity through one pot reaction. Keywords: chemoselective conjugate reduction; dispirocyclopentanebisoxindole scaffolds; metal-free; one-pot operation; reductive cyclization; Introduction There is a vast demand of the structurally complex spirooxindole scaffold which is an
  • derivatives were synthesized on the basis of Michael acceptor ability of 3-alkylidene oxindoles with various donor synthons [16][17][18][19][20][21][22]. However, in spite of the progress in the synthesis of dispirocyclopentanebisoxindoles with concise structural and stereochemical diversity, the one-pot
  • generation of new cascade reactions to construct carbo- and heterocyclic moieties [27][28], we aimed to synthesize dispirocyclopentanebisoxindoles in one pot operation using a new protocol. Chemical hydrogenation of double bonded compounds like α,β-unsaturated ketones, approaching to saturated ketones, is an
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Published 27 Apr 2022

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

Graphical Abstract
  • deposition of gold on metallic fluorides allowed the one-pot hydroacetylation of menadione (10) to diacetylated menadiol 72, while the deposition of gold on silica allowed only the hydrogenation of 10 to 14 (Scheme 22B). The authors also observed that catalysis by hydroxylated fluorides led to a higher
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Published 11 Apr 2022

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

Graphical Abstract
  • Sangram Gore Sundarababu Baskaran Burkhard Konig Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, D-93040 Regensburg, Germany 10.3762/bjoc.18.37 Abstract A facile one-pot synthesis
  • -unsubstituted 3,4-dihydropyrimidinone-4-carboxylate derivatives by employing oxalacetic acid as a β-ketoester equivalent in the presence of TFA via a Biginelli reaction [23]. Lam and Fang reported the same synthesis under microwave conditions [24]. Very recently, Kambappa and co-workers reported a one-pot
  • plays a triple role as solvent, catalyst and as reactant and furnishes the functionalized 5-unsubstituted dihydropyrimidinone-4-carboxylate derivatives. Conclusion In conclusion, a novel one-pot approach has been developed for the synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylate
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Published 22 Mar 2022

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

Graphical Abstract
  • diffraction analysis and proved to be single diastereoisomers and atropisomers. A plausible mechanism for the one-pot Cu(II)-catalyzed Bpin addition to the isatin-derived ketimine substrate and subsequent homocoupling is described. Keywords: atropoisomer; bis(pinacolato)diboron; 3,3′-bisoxindole; N-tert
  • 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
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Published 10 Mar 2022

New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

  • Long Zhao,
  • Mao-Lin Yang,
  • Min Liu and
  • Ming-Wu Ding

Beilstein J. Org. Chem. 2022, 18, 286–292, doi:10.3762/bjoc.18.32

Graphical Abstract
  • of their derivatives [12][13][14][15][16][17][18][19][20][21][22]. For example (Scheme 1), a one-pot Tf2O-mediated assembly of amides, amines, and ketones provided 3,4-dihydroquinazolines in good yields via successive triflic anhydride-mediated amide dehydration, ketimine addition, and Pictet
  • . Most of the reactions took place smoothly to give the corresponding 3,4-dihydroquinazolines 8 in good yields (Scheme 3 and Table 2). Various isocyanates and secondary amines can be used in the above one-pot cyclization to prepare 3,4-dihydroquinazolines 8. As indicated in Table 2, when aromatic
  • temperature, thioureas 10 were also successfully transformed into 4H-3,1-benzothiazines 11 via intramolecular nucleophilic substitution (Scheme 4). The results were listed in Table 3. Various secondary amines can be used in this one-pot cyclization to prepare 4H-3,1-benzothiazines 11. As indicated in Table 3
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Published 04 Mar 2022

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

  • Surendran Amrutha,
  • Sankaran Radhika and
  • Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

Graphical Abstract
  • cross-coupling reactions Homogeneous green protocols Tsai et al. discussed an efficient, simple and environmentally friendly method for the coupling of arylynols 3 with an aryl halide [21]. This strategy discloses a one pot reaction catalyzed by FeCl3 in an aqueous medium associated with the cationic
  • products. Both, asymmetric and symmetric alkynes were synthesized by this one pot method without the use of any organic solvent. For a better yield of the coupled alkyne product, Zn powder was used as a reductant. Lower yields were obtained by the use of ortho-substituted arylynols as the substrate due to
  • reduce the negative impacts on both the environment and health factors. As a developing field of organic synthesis, greener areas have to be explored further and to the best of our knowledge, this review is the first attempt in this area. One pot Sonogashira coupling of aryl iodides with arylynols in the
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Published 03 Mar 2022

Synthesis and late stage modifications of Cyl derivatives

  • Phil Servatius and
  • Uli Kazmaier

Beilstein J. Org. Chem. 2022, 18, 174–181, doi:10.3762/bjoc.18.19

Graphical Abstract
  • NMR spectra. The solubility issues forced us to investigate also other modification protocols. Thus, macrocycle 11 was subjected to an ozonolysis with subsequent Wittig reaction in a one-pot manner (Scheme 4). Performing the ozonolysis in presence of pyridine led to immediate reduction of the primary
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Published 04 Feb 2022

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

  • Thaipparambil Aneeja,
  • Cheriya Mukkolakkal Abdulla Afsina,
  • Padinjare Veetil Saranya and
  • Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

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  • )benzimidazole or its N-alkylated derivatives as the ancillary ligands (N^N) [43]. The prepared Ru(II) derivatives were found efficient in the synthesis of α-amino nitriles from amines via a one-pot strategy. This synthetic pathway comprises two consecutive reactions including photooxidation of the amine and the
  • trimethylsilyl cyanide (TMSCN) in acetonitrile solvent under CFL light irradiation. 4 Miscellaneous An efficient methodology for the synthesis of α-aminonitriles via the one-pot coupling of aldehydes, amines and trimethylsilyl cyanide was reported [46]. This reaction was catalyzed by RuCl3 and used acetonitrile
  • carbonyl compounds under environmentally benign conditions. This method provides an efficient synthetic route towards alkyl iodides and nitriles in one pot. Carbonyl compounds such as cinnamaldehyde, acetophenone, and cyclohexanone etc. were well tolerated in this reaction and afforded the corresponding
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Published 04 Jan 2022

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

Graphical Abstract
  • through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products. Keywords: asymmetric catalysis; cyclization reaction; Michael addition; one-pot three-component reaction; spirobarbiturates; Introduction Indane scaffolds exist in various
  • the basic reaction conditions (Scheme 5b). A one-pot reaction of three available starting materials was tested using CH2Cl2 as the solvent. The one-pot reaction of 1,3-dimethylbarbituric acid (6), benzaldehyde (7), and 2-isothiocyanato-1-indanone (1a) proceeded smoothly to provide the desired product
  • 3aa in 80% yield with 95% ee and >20:1 dr (Scheme 6a). In addition, the one-pot reaction of 1,3-dimethylbarbituric acid (6), m-bromobenzaldehyde (8), and 2-isothiocyanato-1-indanone (1a) was also investigated, and the reaction yield (80%) was lower than before, but the stereoselectivity (>20:1 dr, >99
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Published 04 Jan 2022

Stepwise PEG synthesis featuring deprotection and coupling in one pot

  • Logan Mikesell,
  • Dhananjani N. A. M. Eriyagama,
  • Yipeng Yin,
  • Bao-Yuan Lu and
  • Shiyue Fang

Beilstein J. Org. Chem. 2021, 17, 2976–2982, doi:10.3762/bjoc.17.207

Graphical Abstract
  • one pot. The deprotonation step, and the isolation and purification of the intermediate product after deprotection using existing approaches are no longer needed when the one-pot approach is used. Because the stepwise PEG synthesis usually requires multiple PEG elongation cycles, the new PEG synthesis
  • group, PEG elongation is achieved in two steps – deprotection and coupling – in only one pot (Scheme 1). There is no need to isolate and purify the intermediate between deprotection and coupling, and the deprotonation step is not needed. Our results show that the synthesis is far more convenient than
  • known methods, and high quality of monodisperse PEGs can be obtained in acceptable to high yields. Results and Discussion For a base-labile protecting group to be useful in PEG synthesis using the one-pot PEG elongation approach, it needs to meet two criteria: (1) The protecting group can be removed
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Published 28 Dec 2021

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

  • Tanmoy Halder and
  • Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

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  • involving the [1 + (1 + 1 = 2)] assembly, followed by a one-pot synthesis involving [1 + 1 + 1] strategy from the corresponding monosaccharides. The one-pot method provided a higher yield of the protected trisaccharide intermediate (73%) compared to the two step synthesis (66%). The protected trisaccharide
  • was then deprotected and N-acetylated to finally afford the desired trisaccharide repeating unit as its α-p-methoxyphenyl glycoside. Keywords: capsular polysaccharide; carbohydrate vaccines; O-antigen; oligosaccharide synthesis; one-pot synthesis; Introduction O-antigens or O-specific
  • co-worker accomplished the total synthesis of a O-polysaccharide of Providencia alcalifaciens O22 via a one pot assembly of the oligosaccharide unit [36]. Recently in 2020 Werz and co-workers completed the total synthesis of a tri-, hexa-, and heptasaccharide of the O-polysaccharide of Providencia
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Published 13 Dec 2021

A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

  • Yuki Yamamoto,
  • Akihiro Tabuchi,
  • Kazumi Hosono,
  • Takanori Ochi,
  • Kento Yamazaki,
  • Shintaro Kodama,
  • Akihiro Nomoto and
  • Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

Graphical Abstract
  • methyl ethyl ketone (MEK) was as effective. In addition, in situ-generated α-bromo-δ-valerolactone was directly converted into a sulfur-substituted functional lactone without difficulty by reacting it with a sulfur nucleophile in one pot without isolation. This new bromination system is expected to
  • facilitate the industrial use of α-bromolactones as important intermediates. Keywords: α-bromolactone; metal-free; one-pot operation; tetraalkylammonium hydroxide; two-phase system; Introduction Lactones are important heterocycles in the organic chemistry, materials science, and medicinal chemistry fields
  • through ring-closing reactions that involve the elimination of HBr; notably, ring-closure is successfully promoted in a two-phase system (Scheme 1b). Furthermore, we also report the simple one-pot transformations of lactone derivatives using α-bromolactones as key intermediates. Results and Discussion We
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Published 09 Dec 2021
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