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Search for "benzyl" in Full Text gives 971 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

  • Houchao Xu,
  • Anne Wochele,
  • Minghe Luo,
  • Gregor Schnakenburg,
  • Yuhui Sun,
  • Heike Brötz-Oesterhelt and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

Graphical Abstract
  • -tryptophan (5) that was converted through a standard transformation into the methyl ester 6 and then through sequential reductive aminations with benzaldehyde and paraformaldehyde into 7 (Scheme 2) [13]. Cleavage of the benzyl group by catalytic hydrogenation afforded 8 that was coupled with tert
  • step using milder conditions (Scheme 3). The newly developed synthesis started from 7 that was Boc-protected at the indole to yield 11. Removal of the benzyl group by catalytic hydrogenation to 12 was followed by coupling with benzyloxycarbonyl (Cbz) and methoxymethyl (MOM)-protected threonine to give
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Published 07 Sep 2022

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

  • Mana Kitano,
  • Tsuyoshi Saitoh,
  • Shigeru Nishiyama,
  • Yasuaki Einaga and
  • Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

Graphical Abstract
  • propose a reaction mechanism (Table 2). First, we carried out the electrolysis of 1 in MeCN–MeOH to confirm whether the reaction intermediate is a radical or cationic species (Table 2, entry 1). As a result, methyl cumyl ether, a methoxy adduct to the benzyl position of 1, was obtained as the main product
  • of cumene hydroperoxide as a starting material afforded acetophenone [18]. It should be noted that the tertiary carbon at the benzyl position is a key for the present molecular transformation, since acetophenone was yielded in 19% as the main product by the electrolysis of sec-butylbenzene as a
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Published 07 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
  • our study with the optimization of the arylthio group of thioglycoside 1, carrying an unprotected 4-OH group, an acetyl-protected 3-OH unit, a benzyl-protected 6-OH group, and a phthaloyl-protected 2-NH2 unit (Figure 2) [3]. Electrochemical polyglycosylation was performed by a sequential two-step
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Published 30 Aug 2022

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

  • Kouichi Matsumoto,
  • Yuta Hayashi,
  • Kengo Hamasaki,
  • Mizuki Matsuse,
  • Hiyono Suzuki,
  • Keiji Nishiwaki and
  • Norihito Kawashita

Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

Graphical Abstract
  • with the vinyl group did not occur (Table 3, entry 7), but the reaction of compound 15 with the allyl group formed 16 in 34% yield (Table 3, entry 8). Finally, benzyl 2-chloroacetate (17) produced the corresponding compound 18 in 31% yield (Table 3, entry 9). The current electrolysis reaction can be
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Published 29 Aug 2022

Electrochemical formal homocoupling of sec-alcohols

  • Kosuke Yamamoto,
  • Kazuhisa Arita,
  • Masashi Shiota,
  • Masami Kuriyama and
  • Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

Graphical Abstract
  • anode-free electrochemical protocol for the synthesis of pinacol-type vic-1,2-diols from sec-alcohols, namely benzyl alcohol derivatives and ethyl lactate. The corresponding vic-1,2-diols are obtained in moderate to good yields, and good to high levels of stereoselectivity are observed for sec-benzyl
  • ][16][17][18]. In addition to the reductive coupling of carbonyl compounds, oxidative homocoupling reactions of benzyl alcohols under transition metal- or semiconductor-based photoredox catalysis have been demonstrated as attractive approaches to access vic-1,2-diols [19][20][21][22][23
  • ]. Kim et al. reported the formation of vic-1,2-diols in the sacrificial anode-free electrocarboxylation of 1-phenylethanol and benzyl alcohol which involves tetramethylpiperidine-1-oxyl-mediated alcohol oxidation as an anodic event [46]. However, vic-1,2-diols were obtained only as minor products and
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Published 22 Aug 2022

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

  • Hisanori Senboku,
  • Mizuki Hayama and
  • Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

Graphical Abstract
  • ) [22][23]. We also succeeded in generating N-acyliminium ions from N,N-dimethylformamide (DMF) used as a solvent in the electrochemical carboxylation of benzyl bromides. Electrolysis of benzyl bromides in DMF containing 0.1 M Bu4NBF4 and iPr2NEt (1 equiv) using an undivided cell equipped with a Pt
  • yield. To our surprise, we found that electrolysis of N-benzylindole (4b) at −10 °C under the conditions of 20 mA/cm2 of current density and a lower concentration (0.05 M) of iPr2NHEtBF4 in DMA with 3-6 F/mol of electricity resulted in removal of the benzyl group followed by amidomethylation at the
  • proton source (supporting electrolyte), iPr2NHEtBF4, caused competitive electrochemical reduction of a proton and the N-benzyl group of 5b at the cathode. We also carried out electrochemical amidomethylation of indole (4c) and found that a mixture of 3-amidomethylated indole 5c and N,3-diamidomethylated
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Published 18 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
  • the two benzyl groups on 7b slowed the reaction. Encouraged by the above mentioned results, we then tested N-aryl carbonylimidazoles in the reaction. To our delight, N-aryl carbonylimidazoles with either electron-donating (9b and 10b) or electron-withdrawing groups (11b, 16b and 17b) on the aryl rings
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Published 17 Aug 2022

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

  • Yi-Lun Li,
  • Zhaojiang Shi,
  • Tao Shen and
  • Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

Graphical Abstract
  • ). The enol acetate A first undergoes anodic oxidation to form a radical cation intermediate B, which is then intercepted by azidotrimethylsilane to afford the benzyl radical C. Subsequently, this radical is further anodically oxidized to its oxocarbenium ion intermediate D, which finally reacts with
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Published 12 Aug 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

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

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

Graphical Abstract
  • be seen that the C–C double bond is connected to two methoxycarbonyl groups. Though one hydroxy group exists on the reactive allyl position and benzyl position, it still is present in the molecule and did not give the cyclopentadiene by further elimination of water. In order to obtain the
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Published 08 Aug 2022

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

  • Daniele Rocco,
  • Ana A. Folgueiras-Amador,
  • Richard C. D. Brown and
  • Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

Graphical Abstract
  • (methyl, isopropyl and benzyl alcohols) were used and the results are shown in Table 3. All the experiments were carried out using a solution of 0.1 M of BMImBF4 in acetonitrile (20 mL) as catholyte, stainless steel as cathode, C/PVDF as anode, in a divided cell, under N2 atmosphere, at room temperature
  • minutes and then the corresponding alcohol was added and the reaction was stirred for two hours at room temperature. Workup and column chromatography yielded esters 3a–c and unsaturated esters 4a,b as byproducts. Good yields were obtained using benzyl and methyl alcohols (73% and 68%, respectively), while
  • (m, 3H), 3.65 (s, 3H), 2.94 (t, J = 7.9 Hz, 2H), 2.62 (dd, J = 8.4 Hz, 7.3 Hz, 2H) ppm; 13C NMR (CDCl3) δ 173.3, 140.5, 128.5, 128.5, 128.3, 126.3, 51.6, 35.7, 30.9 ppm. Benzyl 3-phenylpropanoate (3b): Spectral data are consistent with those reported in the literature [43]. 1H NMR (CDCl3) δ 7.19–7.39
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Published 05 Aug 2022

On Reuben G. Jones synthesis of 2-hydroxypyrazines

  • Pierre Legrand and
  • Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

Graphical Abstract
  • } (1.71 g, 66%) both as white powders. 3-Benzyl-5-phenylpyrazin-2-ol (3{1,2}): NMR data were identical with those reported [29]. 3-Benzyl-6-phenylpyrazin-2-ol (4{1,2}): HRMS (m/z): [M + H]+ calcd for C17H15N2O, 263.1178; found, 263.1179. 1H NMR (DMSO-d6) δ 12.27 (br s, 1H), 7.82 (m, 3H), 7.48 (m, 3H
  • (DMSO-d6) δ 158.9, 156.0, 139.5, 129.5, 128.6, 126.6, 126.3, 122.6, 39.1. Preparation of 3-benzyl-5-methylpyrazin-2-ol (3{4,2}). A 40% solution of methylglyoxal (1.94 g, 10.8 mmol) and phenylalanine amide hydrochloride (1.97 g, 9.8 mmol) were dispersed in methanol (26 mL). This was cooled to −78 °C
  • (m, 1H), 3.95 (s, 2H), 2.15 (s, 3H); 13C NMR (DMSO-d6) δ 157.0, 155.2, 138.7, 130.9, 129.4, 128.7, 126.6, 123.6, 38.7, 9.5. Preparation of 3-benzyl-5-(4-(benzyloxy)phenyl)pyrazin-2-ol (3{5,2}). The crude 2-(4-(benzyloxy)phenyl)-2-oxoacetaldehyde (1{5}), prepared as described on page 15 of a patent
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Published 29 Jul 2022

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

Graphical Abstract
  • -oxides 42 and 44 in moderate 54–63% yields via the intramolecular copper-catalyzed cross-coupling of ethyl/benzyl 2-bromobenzylphosphonamidates 41 or P-(2-bromobenzyl)-P-(methyl)phosphinamide (43) as a key step. They were prepared from 2-bromobenzyl bromide (38) via three and four steps, respectively
  • to N atom to generate the zwitterionic 2-((methylamino)benzyl)(phenyl)phosphinic acid 53’, which was further converted into 1-methyl-2-phenyl-1,3-dihydrobenzo[d][1,2]azaphosphole 2-oxide (56a, R = Me) in excellent yield under heating or treatment with DCC. On the other way, methyl (2-aminobenzyl
  • diphenyl-N-benzyl-N-methylphosphinamide (107) in the presence of sec-butyllithium followed by treatment with methanol, deuterium oxide, methyl iodide, and benzaldehyde, affording a series of cyclohexadiene-fused γ-phosphinolactams 108–112 in low regio- and stereoselectivies (Scheme 21) [46]. They further
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Published 22 Jul 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
  • -triazoles [33]. Based on these findings, we examined the reaction of Cu-mediated AAC. The reaction of 4aa with benzyl azide in the presence of one equivalent of CuI and pentamethyldiethylenetriamine (PMDETA) in THF at 60 °C gave the desired 5-selanyl-1,2,3-triazole 8 in 72% yield. This reaction yielded a
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Published 19 Jul 2022

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

  • Maxime Pypec,
  • Laurent Jouffret,
  • Claude Taillefumier and
  • Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

Graphical Abstract
  • -methylhydrazine as a submonomer was adopted in this work (Figure 2). Benzyl bromoacetate, rather than tert-butyl bromoacetate, successfully used in the past for the synthesis of peptoids in solution [22], was chosen as the starting substrate to ensure orthogonality of the C-terminal protecting group with respect
  • to the Boc side chain protections. For the submonomer solution-phase synthesis of monomer 1 and oligomers 2–5, modifications from the standard synthesis conditions were required, notably for the substitution reaction. Thus, the first substitution reaction between benzyl bromoacetate and N-Boc-N
  • studied in detail. Computational studies For the theoretical calculations, acetyl N-(methylamino)dimethylamide model peptoids (Ac-N(NMe)n-NMe2) were used instead of the corresponding synthesized benzyl esters. The model structures were generated using the coordinates extracted from the single crystal X
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Published 14 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
  • -dimethylbarbituric acids or 2-arylidene-1,3-cycloketones efficiently afforded diverse cyclic spirotetrahydrocarbazoles in good yields and with high diastereoselectivity (reaction 3 in Scheme 1). Results and Discussion Initially, (E)-1-benzyl-3-(2-oxo-2-phenylethylidene)indolin-2-one, benzaldehyde, and 2-methylindole
  • applied in such catalytic system. Under the same reaction conditions, the three-component reaction of 2-methylindole, benzaldehyde and 2-(1-benzyl-2-oxoindolin-3-ylidene)malononitrile reacted smoothly to give the expected spiro[carbazole-2,3'indolines] in 51% yield with a diastereometric ratio (dr) value
  • = 1:5–1:8) as eluent to give pure 1a–j and 1a’–j’. 2-Benzoyl-1'-benzyl-4-phenyl-1,2,4,9-tetrahydrospiro[carbazole-3,3'-indolin]-2'-one (1a): Purple solid, 61%, mp 182–185 °C; 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H, NH), 7.89 (d, J = 7.2 Hz, 1H, ArH), 7.54 (t, J = 7.2 Hz, 1H, ArH), 7.43–7.39 (m, 3H, ArH
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Published 07 Jul 2022

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

  • Durbis J. Castillo-Pazos,
  • Juan D. Lasso and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

Graphical Abstract
  • secondary carbon atom at 40 °C (Scheme 2). Furthermore, increasing the temperature to 70 °C was not found to generate the product and instead resulted in slight decomposition of the starting materials. Attempting to trap the sulfinate nucleophiles with primary benzyl bromide (4) with catalytic sodium iodide
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Published 04 Jul 2022

An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates

  • Timur O. Zanakhov,
  • Ekaterina E. Galenko,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2022, 18, 738–745, doi:10.3762/bjoc.18.74

Graphical Abstract
  • pyridone 2n can be quantitatively benzylated by benzyl chloride to give derivative 17. Conclusion A method has been developed for the preparation of 2-alkyl-6-aryl-, 2-aryl-6-aryl and 2,6-diaryl-5-aryl/hetaryl-substituted derivatives of 4-oxo-1,4-dihydropyridine-3-carboxylic acid 2 via Mo(CO)6-mediated
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Published 23 Jun 2022

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

Graphical Abstract
  • , the residue was subjected to column chromatography with petroleum ether/ethyl acetate 15:1 (v/v) as eluent to give the pure product 3a–m for analysis. rel-(1R,3R)-1'-Benzyl-5'-methyl-6-((Z)-4-methylbenzylidene)-2',5-dioxo-3-(p-tolyl)spiro[cyclohexane-1,3'-indoline]-2,2-dicarbonitrile (3a): white solid
  • solution was stirred at 65 °C for six hours. After removing the solvent at reduced pressure, the residue was subjected to column chromatography with petroleum ether/ethyl acetate 15:1 (v/v) as eluent to give the pure product 5a–e for analysis. Ethyl rel-(1S,2S,6R)-1'-benzyl-5'-chloro-3-((Z)-4
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Published 14 Jun 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
  • . Reduction of the quaternary ammonium salt 28 with sodium borohydride gave tetrahydroquinoxaline 29. Its reaction with trifluoroacetic anhydride (TFAA) to give 30 and removal of the benzyl group by catalytic hydrogenation afforded N-trifluoroacetyl-1,2,3,4-tetrahydroquinoxaline (31). Compound 31 was then
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Published 10 Jun 2022

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

  • Dongming Zhang,
  • Bin Lv,
  • Pan Gao,
  • Xiaodong Jia and
  • Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

Graphical Abstract
  • )benzene was treated with 2a. Moreover, benzyl chloride and benzyl bromide tolerated the reaction conditions, affording the aryl-phthalimidated products of which the ortho and para products were the major isomers. It is also shown that disubstituted and trisubstituted arenes successfully reacted to give
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Published 03 Jun 2022

Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold

  • Anastasia Vepreva,
  • Alexander S. Bunev,
  • Andrey Yu. Kudinov,
  • Grigory Kantin,
  • Mikhail Krasavin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2022, 18, 533–538, doi:10.3762/bjoc.18.55

Graphical Abstract
  • yields (Table 1, entries 2–5). In the case of N-benzyl-substituted DAS, byproduct azine 4 was detected by NMR analysis (Table 1, entry 6). The formation of these byproducts was also observed in the case of other DAS bearing alkyl groups at the nitrogen atom (Table 1, entries 10–13) as well as in the case
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Published 11 May 2022

BINOL as a chiral element in mechanically interlocked molecules

  • Matthias Krajnc and
  • Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

Graphical Abstract
  • , which leads to a greater distance between the amine and the chiral macrocycle with increasing chain length. For rotaxanes (R,R/S)-30d–f, which commonly feature a p-xylylene-linker, but different N-substituents, it was found the N-benzyl group gives rise to the best diastereoselectivity (79/55/95% de for
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Published 06 May 2022

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

Graphical Abstract
  • reacted with two equiv 3-nitro-5-(trifluoromethyl)benzyl bromide (2) in the presence of a base to afford the dinitro compounds 3a–f in moderate to excellent yields (Scheme 1a). The diminished yield for product 3d was probably caused by the large steric hindrance of the 3-pentyl substituent. Reduction of
  • product in 65% yield with 68% ee (8al). The reactions for S-benzyl and S-ethyl substrates became sluggish and afforded the products in 34–48% yields in 96 h with very low selectivity (8am and 8an). For the S-tert-butyl substrate, only trace conversion was observed. Macrocyclic effect and catalytic
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Published 02 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
  • indoline ring was also investigated. Varieties of N-protected (Me, Et, propyl, benzyl and allyl) 3-phenacylideneoxindoles were used and provide good to excellent yield of the dimerized products (Scheme 2, Scheme 3). During the detailed study of the reaction, we conducted the reaction with 2-(2-oxindole-3
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Published 27 Apr 2022

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

Graphical Abstract
  • % water, 5% methanol, room temperature, 2 hours). The results showed that phenyl, benzyl, and ethyl β-ketoesters or β-ketoamides reacted smoothly with the phenyl hydroximoyl chlorides and gave the corresponding 3,4,5-trisubstituted isoxazoles 3n–w in good to excellent yields (Figure 4). Generally, the
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Published 22 Apr 2022
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