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Search for "functionality" in Full Text gives 611 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

  • Yasuhiro Igarashi,
  • Yiwei Ge,
  • Tao Zhou,
  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Naoya Oku and
  • Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

Graphical Abstract
  • repeated cadaverine–succinic acid motifs terminated by a hydroxamic acid functionality, were elucidated by NMR and negative MS/MS experiments. Compounds 1–3 were inactive against bacteria and a yeast but displayed cytotoxicity against 3Y1 rat embryonic fibroblasts and P388 murine leukemia cells at GI50 in
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Published 13 Jan 2022

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

  • Sandeep Kumar,
  • Jyotirmoy Maity,
  • Banty Kumar,
  • Sumit Kumar and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

Graphical Abstract
  • eventually brought about the need for newly designed and improved anti-HIV drugs with respect to their improved pharmacological properties [20]. With an idea to keep the presence of azide functionality and to introduce structural rigidity, Marquez et al. [21] developed a methodology for the synthesis of
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Published 11 Jan 2022

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

  • Shun Saito,
  • Kanji Indo,
  • Naoya Oku,
  • Hisayuki Komaki,
  • Masashi Kawasaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

Graphical Abstract
  • H-7 to C-9, H-8 to C-6, and H-10 to C-8, thus completing an alkyl chain part. The remaining atomic composition was CHO2, and despite the lack of evidentiary HMBC correlations, placing a carboxylic acid functionality at the open end (C-2) was reasonable in consideration of the chemical shift of the
  • molecular formula was determined to be C18H22N2O3 based on its NMR and HR–ESI–TOFMS data (m/z 313.1556 [M – H]–, Δ – 0.2 mmu), corresponding to nine degrees of unsaturation. The UV spectrum, exhibiting the absorption maxima at 229 and 282 nm, was typical of an indole functionality. The IR absorption bands
  • , and two amino protons. The remaining OH group should be a part of a carboxylic acid functionality considering the lack of oxygenated carbons besides carbonyls, and two degrees of unsaturation, not accounted for by double bonds, were consistent with the indole ring. As expected, assembling the above
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Published 16 Dec 2021

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

Graphical Abstract
  • late. Introduced by Tietze, cascade reactions are sequences of transformations where subsequent transformations occur only in virtue of functionality formed in previous steps [47]. This process repeats until a product stable under the reaction conditions is formed and the reaction terminates. Compared
  • with the reductive addition or difunctionalization of the π-system; however, it has been demonstrated the radical intermediate can go through a SET oxidation/elimination to recover the initiating π-functionality. In this review, Fe-catalyzed domino coupling reactions involving π-systems will be
  • first three-component alkenylboration of alkenes 50 (Scheme 9) [78]. The authors noted the described methodology regioselectively installs both the boryl functionality and olefin across both activated and unactivated π-systems 50; however, the later required the use of (dppe)FeBr2 in DMF to deliver
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Published 07 Dec 2021

Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

  • Nicolai Wippert,
  • Martin Nieger,
  • Claudine Herlan,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2021, 17, 2773–2780, doi:10.3762/bjoc.17.187

Graphical Abstract
  • 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group. Keywords: cyclization; diazonium chemistry; pyrazoles
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Published 22 Nov 2021

Me3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

  • Krishna M. S. Adusumalli,
  • Lakshmi N. S. Konidena,
  • Hima B. Gandham,
  • Krishnaiah Kumari,
  • Krishna R. Valluru,
  • Satya K. R. Nidasanametla,
  • Venkateswara R. Battula and
  • Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

Graphical Abstract
  • suitably tailored benzonitriles 3 were cyclized in an intramolecular fashion by installing nuclophilic nitrogen onto the nitrile functionality would generate 1-aminoisoquinolines. Herein we describe our efforts on a Me3Al-mediated nucleophilic addition followed by an intramolecular cyclisation of 2-(2-oxo
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Published 16 Nov 2021

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • -1,3-oxathiolane derivative. Further, reduction of the ester functionality with borane dimethyl sulfide at −15 °C afforded the corresponding 2-(hydroxymethyl)-1,3-oxathiolane in 50% yield. It was further treated with benzoyl chloride in the presence of triethylamine (TEA), which provided the desired
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Published 04 Nov 2021

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

  • Pratibha Sharma,
  • Raakhi Gupta and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

Graphical Abstract
  • ][5][6][7]. The reaction involving a nitrogen-based nucleophile as the Michael donor is known as the aza-Michael reaction (aza-MR). In view of its ability to introduce a nitrogen-containing functionality at the β-position of an activated alkenyl- or alkynyl-substrate, over the years, it has developed
  • catalytic systems, namely arylboronic acid alone, its dual combination with chiral thiourea and integrated catalyst having boronic acid functionality in the chiral thiourea molecule. The dual combination of arylboronic acid with chiral thiourea was found as effective as arylboronic acid alone for the
  • intermolecular asymmetric Michael addition of alk-2-enoic acids 68 with O-benzylhydroxylamine (69) giving racemic mixture of the product in poor yield. However, the integrated catalyst having boronic acid functionality in the chiral thiourea molecule gave the desired β-benzyloxyamino acid as the single product
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Published 18 Oct 2021

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

  • Luke O. Jones,
  • Leah Williams,
  • Tasmin Boam,
  • Martin Kalmet,
  • Chidubem Oguike and
  • Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

Graphical Abstract
  • cryogels, degradation of the material is required, yet in many cases the cryogel is still required to perform some functionality during degradation. Therefore, it would be beneficial if the mechanical properties of the cryogel were measured throughout its degradation [25][29]. It has been suggested that
  • ) functionality [97]. The cryogels were synthesised by photochemical crosslinking of N,N-dimethylacrylamide (DMA) and β-CD triacrylate (Figure 7) and aripiprazole was incorporated through inclusion inside the hydrophobic β-CD domains. The release of aripiprazole was monitored at pH 1.2 and 6.8, targeting oral
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Published 14 Oct 2021

Strategies for the synthesis of brevipolides

  • Yudhi D. Kurniawan and
  • A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

Graphical Abstract
  • comprehensive combination of quantum mechanical calculations and experimental spectroscopic analysis of their NMR and ECD data, to have a unique tetrahydrofuran ring instead of the cyclopropane functionality. The absolute configuration of these five compounds were evaluated and all conserved as C6R, C1’S, C2’R
  • the hydrogen source. Following protection of the alcohol moiety with PMBCl, ether 22 was realized in 93% yield. Afterwards, this species was transformed into the γ-keto α,β-unsaturated aldehyde 23 through an NBS-assisted furan oxidation procedure in moderate yield (65%). The keto functionality was
  • desired epoxide 30 after one hour in 85% yield (dr 10:1). This species was next converted to the terminal carbonate derivative 31 to transform the epoxy functionality to a vicinal diol through a two-step manipulation involving protection of the terminal alcohol as Boc derivative followed by BF3·Et2O
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Published 14 Sep 2021

Allylic alcohols and amines by carbenoid eliminative cross-coupling using epoxides or aziridines

  • Matthew J. Fleming and
  • David M. Hodgson

Beilstein J. Org. Chem. 2021, 17, 2385–2389, doi:10.3762/bjoc.17.155

Graphical Abstract
  • heteroatom (hydroxy, amino) functionality (Scheme 2). Results and Discussion Our studies began (Scheme 3) by reaction of BuLi (4 equiv) with a mixture of stannane 4 [6] (2 equiv) and tetramethylpiperidine (TMP, 2 equiv), to generate methoxymethyllithium and LTMP, followed by addition of terminal epoxide 5
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Published 10 Sep 2021

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

  • Satya Kumar Avula,
  • Syed Raza Shah,
  • Khdija Al-Hosni,
  • Muhammad U. Anwar,
  • Rene Csuk,
  • Biswanath Das and
  • Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

Graphical Abstract
  • respective acid chlorides by using thionyl chlorides and these acid chlorides were then made to react with the -OH functionality of metronidazole to get different esters [7]. Here we report a convenient method for the synthesis of aliphatic and aromatic esters of metronidazole. Furthermore, derivatives of
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Published 09 Sep 2021

Base-free enantioselective SN2 alkylation of 2-oxindoles via bifunctional phase-transfer catalysis

  • Mili Litvajova,
  • Emiliano Sorrentino,
  • Brendan Twamley and
  • Stephen J. Connon

Beilstein J. Org. Chem. 2021, 17, 2287–2294, doi:10.3762/bjoc.17.146

Graphical Abstract
  • employ the intriguing substrate 5. In comparison with 2-oxindole 4, compound 5 possesses ester functionality directly attached to the 2-oxindole ring – which would provide a functional handle at this position of considerably greater plasticity than anything previously evaluated in the literature. On the
  • hydrogen bond-donating functionality – while keeping the N-3,5-di-tert-butylbenzyl unit unchanged – were then introduced. Removing the two electron-withdrawing -CF3 groups from the ureaphenyl moiety resulted in diminished enantioselectivity (Table 1, entry 5), whereas increasing the steric demand in this
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Published 02 Sep 2021

Halides as versatile anions in asymmetric anion-binding organocatalysis

  • Lukas Schifferer,
  • Martin Stinglhamer,
  • Kirandeep Kaur and
  • Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

Graphical Abstract
  • the previous sections. For example, catalyst 25 bearing a nucleophilic aminoalcohol functionality interacts with the boronic acid reagent in the Reissert-type reaction with acylated quinolines (Scheme 5b) [36], while the phosphine moiety in the bifunctional phosphinothiourea catalyst 31 allows for
  • excellent yields and enantioselectivities up to 95% and 98% ee, respectively. Cation–π interaction: expanding the functionality of hydrogen bond donor catalysts: The development of hydrogen bond donor anion-binding catalysts mainly focuses on the interaction and binding properties towards the anionic
  • development of an enantioselective aza-Sakurai cyclization (Scheme 12) [70]. In this transformation, a chiral thiourea catalyst 58 with a dibenzothiophene functionality serves as a dual H-bond donor and Lewis base to facilitate the cyclization of hydroxylactams 56. Thus, indolizine and quinolidizine
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Published 01 Sep 2021

Chemical syntheses and salient features of azulene-containing homo- and copolymers

  • Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

Graphical Abstract
  • by using [Pd(allyl)Cl]2 and JackiePhos as a ligand to obtain the polymer 30 in 52% yield. The deprotection of the N-Boc functionality led to the formation of poly[2,6-aminoazulene] 31 in excellent yields (Scheme 7C). The N-Boc-protected polymer 30 possessed good solubility in organic solvents and its
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Published 24 Aug 2021

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

  • Zara M. Seibel,
  • Jeffrey S. Bandar and
  • Tristan H. Lambert

Beilstein J. Org. Chem. 2021, 17, 2077–2084, doi:10.3762/bjoc.17.134

Graphical Abstract
  • handles for derivatization and so represent important achievements for this method. In terms of additional functionality, we found that a thioether substrate could be engaged with reasonably good efficiency and enantioselectivity (Table 2, entry 11). On the other hand, while a nitrile was compatible with
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Published 17 Aug 2021

Progress and challenges in the synthesis of sequence controlled polysaccharides

  • Giulio Fittolani,
  • Theodore Tyrikos-Ergas,
  • Denisa Vargová,
  • Manishkumar A. Chaube and
  • Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Graphical Abstract
  • observed for cellulose [67][79], while the multifluorinated compound formed considerably shorter platelets. Cellulose–xylan [80] and cellulose–chitin [81] hybrids were also obtained upon enzymatic polymerization of the respective dimers. An amino or azido functionality in the C-6 position allows for
  • hydroxy group at C-3 and β-selectivity is easily achieved with the help of anchimeric assistance provided by a 2-O-acyl functionality. Despite these advantages, the synthesis of β(1–6)-Glc polysaccharides appears only in few reports [148][149], with short oligomers being prepared mainly to prove new
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Published 05 Aug 2021

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

  • Ryan M. Alam and
  • John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

Graphical Abstract
  • cation chelation via the N-2 atom electron lone pair and the C-3 substituent X=O functionality, respectively [24]. Tight ion pair formation with the sodium cation and both the N-2 atom and C-3 substituents of the indazole scaffold likely hinders the approach of the electrophile to N-2 and directs
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Published 02 Aug 2021

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

  • Mathias B. Danielsen and
  • Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

Graphical Abstract
  • attempt to introduce high yielding phosphoramidite building blocks suitable for automated ON synthesis, 2′-O-aminoethoxymethyl and 2′-O-aminopropoxymethyl nucleotides were developed. This method introduced the primary amine functionality through an azide reduction [73]. The corresponding monomers 37 and
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Published 29 Jul 2021

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

  • Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

Graphical Abstract
  • install the free NH functionality. These findings highlight the convenience of manganese catalysis for the late-stage benzylic C–H amination of sophisticated bioactive molecules and natural products. The proposed mechanism of the Mn-catalyzed benzylic amination is shown in Figure 6. Initially
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Published 26 Jul 2021

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

  • Christin Walther,
  • Pamela Baumann,
  • Katrin Luck,
  • Beate Rothe,
  • Peter H. W. Biedermann,
  • Jonathan Gershenzon,
  • Tobias G. Köllner and
  • Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

Graphical Abstract
  • , where only the sesquiterpene trichodiene was detected with FPP, while other substrates were not accepted [69]. In contrast, bi-functionality was also observed for the pinene and guaiene synthase from Daldinia eschscholzii EC12 and the pinene and guaiene synthase from Hypoxylon sp. EC28 (Figure 3) [45
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Published 22 Jul 2021

Total synthesis of ent-pavettamine

  • Memory Zimuwandeyi,
  • Manuel A. Fernandes,
  • Amanda L. Rousseau and
  • Moira L. Bode

Beilstein J. Org. Chem. 2021, 17, 1440–1446, doi:10.3762/bjoc.17.99

Graphical Abstract
  • 17, followed by acetonide protection of the 1,3-diol functionality to yield the previously synthesized intermediate 4. The acetonide protecting group was chosen because of its stability under the future reaction conditions in addition to it being a convenient monitor of the relative configuration of
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Published 10 Jun 2021

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

  • Santiago Ramos-Carreño,
  • Ivone Giffard-Mena,
  • Jose N. Zamudio-Ocadiz,
  • Alfredo Nuñez-Rivera,
  • Ricardo Valencia-Yañez,
  • Jaime Ruiz-Garcia,
  • Maria Teresa Viana and
  • Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

Graphical Abstract
  • groups were challenged with WSSV by IM injection, with a dose of 10−6 Son2008 inoculum. (Herein “pellet feed” refers to when animals are fed with treatments, and “oral cavity” refers to when the VLPs treatment is given directly into the oral cavity through a needle to ensure intestinal functionality
  • taken orally was more effective than when merely present in the feed as a coating. Taking the VLP-dsRNA28 orally assures capsid functionality by protecting the dsRNA structure. Administering VLP capsids inside the feed resulted in increased shrimp survival after challenged with the WSSV and treated per
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Published 01 Jun 2021

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

  • Cansu Esen and
  • Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

Graphical Abstract
  • were characterized via FTIR analysis to elucidate structural footprints of CM embedding and vTA photographing. The broad peak in the range from 3639 cm−1 to 3136 cm−1 corresponds to the hydrogen bonding between carboxyl and hydroxy groups with amide functionality of the hydrogel backbone. Significant
  • release which is highly beneficial for agricultural delivery systems. The grand outcome of embedded g-CN-based surface photomodification has significant advantages in terms of its non-toxic process and cost-efficient material resources. Pore substructuring In porous materials, the functionality of the
  • pores is responsible for the main catalytic activity, such as in carbonaceous materials [47][48]. When a network with full functionality cannot be formed easily, one can form a rigid neutral host and modify the pores subsequently. Herein, the nanoporous system is magnified to macropores in hydrogel
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Published 21 May 2021

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

  • Guido Gambacorta,
  • James S. Sharley and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Graphical Abstract
  • performance of these reaction types as a continuous-flow process is provided. Condensation reactions A carbonyl functionality is encountered in the vast majority of fragrance ingredients. The ability therefore to manipulate carbonyl moieties within a molecule will forever serve as an important transformation
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Published 18 May 2021
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