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Search for "building blocks" in Full Text gives 896 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

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

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  • from natural sources or by synthesis via chemical glycosylation [2]. Total syntheses of chitin and chitosan oligosaccharides based on conventional chemical glycosylation of protected monosaccharides as building blocks have already been reported. Convergent synthesis using oligosaccharide building
  • oligosaccharides based on electrochemical preactivation of building blocks, is an alternative method for the synthesis of chitin oligosaccharides [3][4], it is also time-consuming and too sophisticated to prepare oligosaccharides composed of a single repeating structure. Thus, we assume that the electrochemical
  • 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
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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

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  • organic synthesis as versatile building blocks [1][2][3][4][5]. In general, some synthetic procedures for cyclopropane derivatives have been discovered, e.g., the Simmons–Smith reaction and the use of metal carbenoids being two of the more prominent and reliable methods [6][7][8][9]. Aggarwal and
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Published 29 Aug 2022

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

  • Laura Holzhauer,
  • Chloé Liagre,
  • Olaf Fuhr,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

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  • triazoloquinoxaline ligand has a visible influence on the reduction behavior of the complex. Conclusion New derivatives of 1,2,3-triazoloquinoxalines have been synthesized starting from tetrazolo[1,5-a]quinoxalines via CuAAC by varying the alkyne and the residues on the quinoxaline building blocks. During the
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Published 24 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

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  • ]. Such scaffolds are widely utilized as versatile building blocks in the synthesis of biologically active compounds [3][4][5][6][7], chiral auxiliaries [8][9], and chiral ligands [10][11][12][13]. Traditional pinacol coupling reactions are performed with a stoichiometric or even excess amount of low
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Published 22 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

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  • 200240, China 10.3762/bjoc.18.103 Abstract α-Azidoketones are valuable and versatile building blocks in the synthesis of various bioactive small molecules. Herein, we describe an environmentally friendly and efficient electrochemical vicinal oxyazidation protocol of α-arylvinyl acetates to afford
  • ; Introduction Organoazides play important roles in pharmaceutical, bioorthogonal chemistry, and many other interdisciplinary research areas [1][2][3]. Among them, azidoketones are also very versatile building blocks in organic synthesis, pharmaceutical, and materials science [4][5][6]. Therefore, the
  • of α-arylvinyl acetates to access diverse vicinal α-azidoketones. The protocol employs the experimentally simple undivided electrochemical cell and tolerates a broad substrate scope. The obtained α-azidoketones have been shown to be versatile building blocks for the preparation of biologically
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Published 12 Aug 2022

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

  • Dharmendra Das,
  • Akhil A. Bhosle,
  • Amrita Chatterjee and
  • Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

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  • , pharmaceuticals, agrochemicals, and advanced materials [10][11][12][13][14]. The ubiquity of halogen atoms in these synthetic building blocks urges the development of efficient, sustainable, and mild methods for aromatic halogenation. The century-old classical method of using hazardous and corrosive reagents X2
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Published 09 Aug 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

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  • [1][2][3][4][5][6][7][8] and have been widely applied in agrochemicals, medicinal agents, and materials science [9][10]. They are also organic synthetic intermediates and building blocks [7][11][13]. 1,2-Azaphosphaheterocycle oxide derivatives, phosphonolactams and phosphinolactams, are phosphorus
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Published 22 Jul 2022

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

  • Fang-Ru Li,
  • Xiaoxu Lin,
  • Qian Yang,
  • Ning-Hua Tan and
  • Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

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  • minimum C5 isoprenoid building blocks isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), which are produced in the cell via one of two pathways: i) the mevalonate (MVA) pathway includes seven steps from acetyl-CoA (A-CoA); and ii) the 2-C-methyl-ᴅ-erythritol 4-phosphate (MEP) pathway
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Published 21 Jul 2022

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

  • Conrad Kuhwald,
  • Sibel Türkhan and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

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  • technique can be easily automated. Thus, protocols can be iteratively repeated by simply changing building blocks so that compound libraries can be quickly accessed [54][55]. The formation of heterocycles traditionally often requires very harsh conditions, so that high pressure and high temperature can
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Published 20 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

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  • building blocks to decorate the inner cavity of the host would produce efficient types of catalyst, where the substrates get activated for a particular reaction upon interaction with the functional group inside the cavity. Mukherjee et al. have demonstrated the construction of 3D nanocages employing
  • -worker have demonstrated the design and synthesis of urea-functionalized 2D/3D architectures and their catalytic activity. The urea moieties were incorporated within the building blocks and were meant to serve as binding sites for appropriate substrates, therefore, promoting selectivity and reactivity
  • enantiopure tetrahedral Pt12 cage has been previously studied for catalytic Michael addition reactions, but no enantioselectivity was detected because the chiral building blocks were located at peripheral positions thus not sufficiently breaking symmetry within the cavity [73]. Therefore, it was envisioned
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Published 27 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

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  • important functional group transformation for the synthesis of heterocyclic and carbocyclic building blocks and reactive intermediates. Besides the use of various reducing agents, it is observed that tosylhydrazine develops the transition-metal-free and highly chemoselective conjugate reduction of α,β
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Published 27 Apr 2022

The asymmetric Henry reaction as synthetic tool for the preparation of the drugs linezolid and rivaroxaban

  • Martin Vrbický,
  • Karel Macek,
  • Jaroslav Pochobradský,
  • Jan Svoboda,
  • Miloš Sedlák and
  • Pavel Drabina

Beilstein J. Org. Chem. 2022, 18, 438–445, doi:10.3762/bjoc.18.46

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  • substances, because the reduction of the amount of the undesirable stereoisomer to a minimum can suppress possible side effects. The oxazolidine-2-one-type drugs are usually prepared following synthetic methods that utilize available chiral building blocks (e.g., epichlorohydrine, glycidol, 3-chloropropane
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Published 14 Apr 2022

Cs2CO3-Promoted reaction of tertiary bromopropargylic alcohols and phenols in DMF: a novel approach to α-phenoxyketones

  • Ol'ga G. Volostnykh,
  • Olesya A. Shemyakina,
  • Anton V. Stepanov and
  • Igor' A. Ushakov

Beilstein J. Org. Chem. 2022, 18, 420–428, doi:10.3762/bjoc.18.44

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  • building blocks for the production of other important molecules (e.g., amino alcohols, diols, etc.) [40][41][42][43][44][45][46] and potential pharmaceuticals. α-Hydroxyketones are structural subunits of natural products [47][48][49] and compounds possessing immunosuppressant [50], antidepressant [51
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Published 12 Apr 2022

Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions

  • Robin Schulte and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2022, 18, 368–373, doi:10.3762/bjoc.18.41

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  • promising candidates for molecular solar thermal (MOST) energy storage. As in this context there is still the need for new tailor-made derivatives, borylated norbornadienes were synthesized that may be used as versatile building blocks. Thus, the 4,4,5,5-tetramethyl-2-(bicyclo[2.2.1]heptadien-2-yl)-1,3,2
  • -dioxaborolane, whose reactivity in Suzuki–Miyaura couplings has not been investigated, so far [32][33]. To explore the suitability of borylated norbornadienes for Suzuki–Miyaura coupling reactions and thus to provide new useful building blocks for the modular construction of norbornadiene derivatives
  • (HRMS). To assess the suitability of the boronic esters 2a and 2b to be used as building blocks in Suzuki–Miyaura reactions, the Pd-catalyzed cross-coupling reaction of norbornadiene 2a and bromobenzene (4a) was examined under different conditions (Table 1, Scheme 2). First experiments were conducted
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Published 01 Apr 2022

Iridium-catalyzed hydroacylation reactions of C1-substituted oxabenzonorbornadienes with salicylaldehyde: an experimental and computational study

  • Angel Ho,
  • Austin Pounder,
  • Krish Valluru,
  • Leanne D. Chen and
  • William Tam

Beilstein J. Org. Chem. 2022, 18, 251–261, doi:10.3762/bjoc.18.30

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  • -opening reactions of heterobicyclic alkenes are of particular interest [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53], as they provide access to a broad family of synthetic building blocks bearing multiple stereocenters in a single step 2 [54]. Application of these functionalized
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Published 02 Mar 2022

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

  • Kian Donnelly and
  • Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

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  • ]pentane (BCP) building blocks [36], we investigated their use in the oxadiazole-forming reaction. The BCP acid chloride 5 was synthesised from [1.1.1]propellane (3) via the photochemical reaction with isopropyl 2-chloro-2-oxoacetate (Scheme 4). The corresponding BCP acyl hydrazone was then obtained
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Published 25 Feb 2022

Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates

  • Ekta Gupta,
  • Narendra Kumar Vaishanv,
  • Sandeep Kumar,
  • Raja Krishnan Purshottam,
  • Ruchir Kant and
  • Kishor Mohanan

Beilstein J. Org. Chem. 2022, 18, 217–224, doi:10.3762/bjoc.18.25

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  • of enantioselectivity, and the corresponding optically active oxyaminated malonamates were obtained in reasonably good yields. Keywords: enantioselective; malonamate; nitroso aldol reaction; N-selectivity; Takemoto catalyst; Introduction Nitrosoarenes are versatile building blocks frequently
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Published 21 Feb 2022

The role of chemistry in the success of oligonucleotides as therapeutics

  • Pawan Kumar and
  • Tom Brown

Beilstein J. Org. Chem. 2022, 18, 197–199, doi:10.3762/bjoc.18.22

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  • [3], and the field owes a big thanks to all the researchers who have contributed to expanding chemical space of modified nucleotides (building blocks of oligonucleotides). However, discussing these modifications in detail is beyond the scope of this editorial. The use of chemically modified
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Published 14 Feb 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

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  • general, typical syntheses of such natural products start with the synthesis of the unusual building blocks, their incorporation into a linear peptide, which is finally subjected to cyclization at a suitable position. No question, this protocol is well suited to get access to a certain compound, also in
  • the peptide can have a significant effect on the Claisen rearrangement and therefore we synthesized the Cbz- as well as the Boc-protected peptides 8a and 8b. The tripeptide building blocks were previously also used in the Cyl-1 synthesis. Glycine allyl ester 5 was Boc-deprotected to give amine 7 as
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Published 04 Feb 2022

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

  • Malcolm J. D’Souza and
  • Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

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  • , sulfonyl chlorides are good building blocks to intermediates and complex scaffolds of sulfonamides. Gordon, Maskill, and Ruasse [1] have reviewed “Sulfonyl Transfer Reactions” in a broader sense than the coverage of the present contributions. In particular, an appreciable amount of the coverage in the
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Review
Published 17 Jan 2022

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

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  • widely used as building blocks to prepare various heterocyclic peptides [17][18][19][20][21][22]. In particular, 1,2-oxazole amino acid derivatives, such as compounds V [20], VI [21], and VII, VIII [22], can be easily synthesized and are suitable for insertion with the corresponding heterocycle into a
  • -4-carboxylic acid residue was identified directly from the 12.6-million-member DNA-encoded small molecule library using yoctoReactor technology [26]. We have developed efficient protocols that provide easy access to highly functional heterocyclic compounds as novel amino acid-like building blocks by
  • -oxazoles [34][35]. This study aimed to develop and synthesize methyl 5-(cycloaminyl)-1,2-oxazole-4-carboxylates, as new amino acid-like building blocks. This type of functionalized heterocycles could exhibit not only useful biological properties, but also find application as building blocks for the
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Published 12 Jan 2022

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

  • İlknur Polat,
  • Selçuk Eşsiz,
  • Uğur Bozkaya and
  • Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

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  • biological activities [6][7]. Moreover, they can be used as starting substances for different heterocycles, as precursors for the synthesis of polymers, as potential pharmacons, for the synthesis of natural products or analogues, and also as building blocks in drug research [8][9][10][11]. Furthermore, some
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Published 06 Jan 2022

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

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

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

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  • ]. Additionally, halotryptophans were incorporated in pentapeptides as building blocks for macrocyclisation by Suzuki–Miyaura cross-coupling (SMC) aiming at the preparation of bicyclic peptides [71]. Recently, intramolecular SMC has been successfully applied to side chain-to-tail cyclisation between
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Published 03 Jan 2022

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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  • authors [39][40][41][42]. The starting materials 3, 6, and 7 were also amenable to a [1 + 1 + 1] one-pot synthetic strategy by adopting minor synthetic modifications. The monosaccharide building blocks 3, 6, and 7 [43] were synthesized from previously reported compounds 8 [36], 9 [44][45], and 10 [46] as
  • described in Scheme 2. With the monosaccharide building blocks in hand, the galactosamine donor 6 was coupled with galactose acceptor 7 by activation of the thioglycoside using N-iodosuccinimide (NIS) in the presence of TMSOTf to afford the desired disaccharide β-ᴅ-GalpNHTroc-(1→4)-α-ᴅ-Galp (4) in 85% yield
  • analysis for the synthesis of the target trisaccharide 1. Synthesis of the monosaccharide building blocks 3, 6, and 7. Linear synthesis of trisaccharide derivative 2. Synthesis of ᴅ-galactose donor 12. One-pot synthesis of trisaccharide derivative 2. Synthesis of trisaccharide derivative 1. Supporting
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Published 13 Dec 2021

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

  • Qingkai Zeng,
  • Qiumeng Long,
  • Jihong Lu,
  • Li Wang,
  • Yuting You,
  • Xiaoting Yuan,
  • Qianjun Zhang,
  • Qingmei Ge,
  • Hang Cong and
  • Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

Graphical Abstract
  • reduction of 5-nitroisophthalic acid with NaBH4 and BF3·Et2O followed by subsequent bromination with PBr3 [46] and 2-imidazolidinone (6) were used as building blocks. By controlling the molar ratio of 5 and 6 at 1:10 or 6:1 and the reaction conditions, products 7 and 8 were readily accessible with 25.3
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Published 06 Dec 2021
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