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Search for "esterification" in Full Text gives 279 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

  • Guozheng Huang,
  • Simon Schramm,
  • Jörg Heilmann,
  • David Biedermann,
  • Vladimír Křen and
  • Michael Decker

Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66

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  • , Prague 4, CZ-14220, Czech Republic 10.3762/bjoc.12.66 Abstract Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding
  • alcohols and bulky acids: Cherney and Wang observed an elimination of a serine derivative during esterification experiments [23]. During conversion of substituted benzyl alcohols to amines under Mitsunobu conditions, elimination also occurred [24]. Dehydration under Mitsunobu conditions has been applied in
  • and expeditious semi-synthetic preparation of hydnocarpin, hydnocarpin D and isohydnocarpin. Results and Discussion Although silibinin, i.e., silybins A and B, bears three phenolic, one secondary and one primary hydroxy group, selective Mitsunobu esterification typically occurs at the primary C-23 OH
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Published 08 Apr 2016

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

  • Rajeev S. Menon,
  • Akkattu T. Biju and
  • Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

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  • . This is followed by a redox esterification of the latter (47) with enals. The overall process constitutes a one-pot synthesis of hydroxamic esters 48 [45]. Notably, both steps can be performed using the single NHC catalyst 22 under same reaction conditions (Scheme 29). This two-step, one-pot synthesis
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Published 09 Mar 2016

Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones

  • Ping Qian,
  • Bingnan Du,
  • Wei Jiao,
  • Haibo Mei,
  • Jianlin Han and
  • Yi Pan

Beilstein J. Org. Chem. 2016, 12, 301–308, doi:10.3762/bjoc.12.32

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  • [18][19], decarboxylative alkenylation of cycloalkanes with aryl vinylic carboxylic acids [20][21], trifluoromethylthiolation [22], thiolation [23][24], alkenylation [25][26], dehydrogenation−olefination and esterification [27][28], radical addition/1,2-aryl migration [29], cascade alkylation
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Published 17 Feb 2016

Enabling technologies and green processes in cyclodextrin chemistry

  • Giancarlo Cravotto,
  • Marina Caporaso,
  • Laszlo Jicsinszky and
  • Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

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  • esterification of CD was promoted by MW irradiation, while the chitosan coupling used a water-soluble carbodiimide, N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, under US. A mild sonication at rt using HDI enabled efficient CDs reticulation in the presence of lipases (Scheme 7) whose biocatalytic
  • was observed at concentrations up to 333 μg/mL [73]. Separately, a facile and rapid MW-assisted method in water has been used to derivatize graphene nanosheets with (2-hydroxy)propyl-β-CD. The reaction involved the esterification of the HP-β-CD hydroxy groups by the carboxyl groups of graphene oxide
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Published 15 Feb 2016

Recent advances in metathesis-derived polymers containing transition metals in the side chain

  • Ileana Dragutan,
  • Valerian Dragutan,
  • Bogdan C. Simionescu,
  • Albert Demonceau and
  • Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

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  • triazolyl unit was first attached to the η4-cyclopentadiene CpCo(I) complex by click reaction of the corresponding alkyne precursor and then the triazolyl-Co scaffold was incorporated into the norbornene monomer 9 by conventional esterification. It is important to note that the cyclopentadienyl-cobalt-1,3
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Published 28 Dec 2015

Pyridylidene ligand facilitates gold-catalyzed oxidative C–H arylation of heterocycles

  • Kazuhiro Hata,
  • Hideto Ito,
  • Yasutomo Segawa and
  • Kenichiro Itami

Beilstein J. Org. Chem. 2015, 11, 2737–2746, doi:10.3762/bjoc.11.295

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  • was also detected. Furthermore, a significant amount of methyl 2-iodobenzoate (5) was generated through the esterification of a co-product (2-iodobenzoic acid) with methanol. We also tested other iodine(III) reagents such as PhI(OAc)2, PhI(OCOCF3)2 and PhI(OH)(OTs), but they all resulted in lower
  • confirmed that the esterification of 2-iodobenzoic acid takes place to give 5 under the reaction conditions; 2-iodobenzoic acid was smoothly converted to 5 in chloroform/methanol solution at 65 °C. Transmetalation of gold(III) complex B with arylsilane 2 affords monoarylated gold(III) intermediate C. The
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Published 28 Dec 2015

Synthesis of cyclic N1-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

  • Ahmed Mahal,
  • Stefano D’Errico,
  • Nicola Borbone,
  • Brunella Pinto,
  • Agnese Secondo,
  • Valeria Costantino,
  • Valentina Tedeschi,
  • Giorgia Oliviero,
  • Vincenzo Piccialli and
  • Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

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  • 9 we explored two synthetic routes, differing for the degree of esterification at the phosphate moiety, to achieve the cyclization of the 17-membered ring of 4. The treatment of 9 with a mixture of triethylamine/pyridine furnished the phosphodiester product 10 in almost quantitative yield. Instead
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Published 22 Dec 2015

Assembly of synthetic Aβ miniamyloids on polyol templates

  • Sebastian Nils Fischer and
  • Armin Geyer

Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284

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  • , Aβ peptide pentapeptide boronic acids 1 and 2 were synthesized by solid-phase peptide synthesis and studied in esterification experiments with polyhydroxylated templates. The bis-hydroxylated dipeptide Hot=Tap serves as a template of adjustable degree of oligomerization which spontaneously forms
  • boronic esters with peptides of type 1 and 2. Nuclear magnetic resonance can differentiate between regioisomeric boronic esters and identifies preferred sites of esterification on the dimeric template 9. 2-Formylphenylboronic acid (14) is used to link the parent pentapeptide Leu-Val-Phe-Phe-Ala to the
  • example, disulfide [10], acetal [11], imine [12] and boronates [13][14][15][16], to allow the generation of new covalent structures under thermodynamic control. Complete esterification is observed for boronate esters bearing ortho-amines [17]. The conceptual advantage compared to traditional irreversible
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Published 17 Dec 2015

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

  • Tatjana Huber,
  • Lara Weisheit and
  • Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

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  • synthesized in four steps. Esterification with (R)-(+)-citronellic acid (127) yielded a single diastereomer of ester 128. Addition of lithium diisopropylamide to a mixture of 128, trimethylsilyl chloride and triethylamine initiated an Ireland–Claisen rearrangement [63] which gave carboxylic acid 129 in 85
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Published 10 Dec 2015

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

  • Kirk W. Shimkin and
  • Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

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  • and supress polymerization. A detachable ester group can be utilized in order to achieve Z-selective alkene synthesis [37]. In this protocol, an ortho-hydroxy substituted styrene undergoes esterification with a labile α-bromo ester. This positions the reactive radical exclusively on the face of the
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Published 23 Nov 2015

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

  • Jing Lin,
  • Tao Kong,
  • Lin Ye,
  • Ai-ying Zhang and
  • Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

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  • , where x is the feed molar ratio of MA to PPO-PEO-PPO. The products were characterized by means of 1H NMR and GPC analyses (Figure S1 and Figure S2, Supporting Information File 1). The degree of esterification of BrPEPBr determined by 1H NMR was >99%. Additionally, the GPC curves of PEPxM presented a
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Published 23 Nov 2015

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

  • Meriem K. Abderrezak,
  • Kristýna Šichová,
  • Nancy Dominguez-Boblett,
  • Antoine Dupé,
  • Zahia Kabouche,
  • Christian Bruneau and
  • Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

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  • by intramolecular trans-esterification from 6, 7 and 8, as well as cyclic amines by intramolecular cyclization involving primary amine resulting from hydrogenation of the nitrile functionality in 5. All these aspects will be further developed in our group. Cross metathesis of 1 with methyl acrylate
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Published 08 Oct 2015

Recent applications of ring-rearrangement metathesis in organic synthesis

  • Sambasivarao Kotha,
  • Milind Meshram,
  • Priti Khedkar,
  • Shaibal Banerjee and
  • Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

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  • prepared from the corresponding allylic alcohol 63 by esterification with the anhydride 64 derived from cyclobutene. Later, the ester 65, on treatment with the catalyst 1 under toluene reflux conditions followed by treatment with the catalyst 2 furnished the macrolide-butenolides 66 in 42–48% yields via
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Published 07 Oct 2015

Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach

  • Jingjing Wang,
  • Samuel Z. Y. Ting and
  • Joanne E. Harvey

Beilstein J. Org. Chem. 2015, 11, 1815–1822, doi:10.3762/bjoc.11.197

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  • uncharted. In this paper, a three-component reaction between α,β-unsaturated aldehydes, alcohols and the Bestmann ylide is described. The scope of this esterification–Wittig reaction sequence in the synthesis of α,β,γ,δ-unsaturated esters is studied, and the method is applied in an approach towards the
  • . Although fragment syntheses vary, the late-stage fragment assembly of the dactylolide macrocycle has centred mostly around construction of the C1–C5 dienoate by Wittig-type olefination reactions followed by ester hydrolysis and esterification with the C19 hydroxy group, combined with metathesis to form the
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Published 05 Oct 2015

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

  • Louis P. Sandjo,
  • Victor Kuete and
  • Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

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  • ) has been performed by Lotter and Bracher [67]. The route included four steps, but unfortunately, the overall yield was only 7%. Like in method A, the synthesis started with 1,10-phenanthroline to prepare binicotinic acid via oxidative cleavage by potassium permanganate. The esterification took place
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Published 18 Sep 2015

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

  • Ivan Bassanini,
  • Karl Hult and
  • Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

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  • in the esterification of the antineoplastic antibiotics mithramycin (5) catalyzed by Candida antarctica lipase A (CAL-A) and chromomycin A3 (6) catalyzed by Candida antarctica lipase B (CAL-B) [24]. In another report a series of mono-substituted troxerutin esters (7a) were synthesized by action of
  • parent compound 12. A similar approach was followed later on by Lin and coworkers, who described the enzymatic esterification of the nucleoside 5-fluorouridine (13) and of other polyhydroxylated bioactive molecules with divinyl esters of dicarboxylic acids [31][32][33][34][35]. The monovinyl esters
  • once again the well-known efficiency, selectivity and versatility of CAL-B (Novozyme 435) [16]. As in the previous examples, the mixed esters from the first esterification step can be used as acylating agents in the second esterification step. Scheme 3 shows the synthesis of the hybrid compounds 17 and
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Published 09 Sep 2015

Consequences of the electronic tuning of latent ruthenium-based olefin metathesis catalysts on their reactivity

  • Karolina Żukowska,
  • Eva Pump,
  • Aleksandra E. Pazio,
  • Krzysztof Woźniak,
  • Luigi Cavallo and
  • Christian Slugovc

Beilstein J. Org. Chem. 2015, 11, 1458–1468, doi:10.3762/bjoc.11.158

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  • Suzuki coupling as shown in Scheme 2 [14]. The cyano-substituted compound 10 was obtained without difficulty, but esterification of compound 9 was problematic because of purification issues (cf. Supporting Information File 1) so an alternative pathway was established. Starting from 2-bromoaniline upon
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Published 20 Aug 2015

Selected synthetic strategies to cyclophanes

  • Sambasivarao Kotha,
  • Mukesh E. Shirbhate and
  • Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

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Published 29 Jul 2015

Novel carbocationic rearrangements of 1-styrylpropargyl alcohols

  • Christine Basmadjian,
  • Fan Zhang and
  • Laurent Désaubry

Beilstein J. Org. Chem. 2015, 11, 1017–1022, doi:10.3762/bjoc.11.114

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  • type of reaction has not been described before. It provides a useful alternative to the Rautenstrauch rearrangement, the main limitation of which lies on the necessity to have the alcohol esterified (Scheme 2) [8]. Indeed, in many cases, this esterification occurs in low yield, or may even be
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Published 15 Jun 2015

Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8–DMSO: application to the synthesis of vernakalant

  • Dnyaneshwar N. Garad,
  • Subhash D. Tanpure and
  • Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

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  • , hydrothermal cyclization, H2SO4 in acetic acid, PEG-600, silica supported TaCl5, esterification using inorganic base and alkylating agent followed by heating in the presence of tetrabutylammonium bromide, diphenyl 2-oxo-3-oxazolinylphosphonate and Et3N as well as several other conditions have been reported in
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Published 12 Jun 2015

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

  • Hana Doušová,
  • Radim Horák,
  • Zdeňka Růžičková and
  • Petr Šimůnek

Beilstein J. Org. Chem. 2015, 11, 884–892, doi:10.3762/bjoc.11.99

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  • byproducts. A better and less time-consuming route to 10 consists of the reaction of 2-halobenzaldehyde 7 with Meldrum´s acid in the presence of HCOOH/Et3N system with a total yield of 61–67% (step f in Scheme 4). The last step for both methods was the esterification of acids 10a,b (step e in Scheme 4). β
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Published 27 May 2015
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  • procedures for acidic O-acylation of amino alcohols, Luh and Chong reported a method for selective aromatic esterification of amino alcohols in 1978, consisting of acylations of an amino
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Published 08 Apr 2015

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

  • Qiu Sun,
  • Jörg Heilmann and
  • Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

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  • . KUNZE, Theaceae). It is the esterification product of epigallocatechin and gallic acid. Many studies provide evidence that EGCG modulates multiple signal transduction pathways, controlling the unwanted proliferation of cells. It inhibits the activation of HIF-1α, NF-κB and VEGF expression, thereby
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Published 16 Feb 2015

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: synthesis and characterization

  • Mahabaleshwara Subrao,
  • Dakshina Murthy Potukuchi,
  • Girish Sharada Ramachandra,
  • Poornima Bhagavath,
  • Sangeetha G. Bhat and
  • Srinivasulu Maddasani

Beilstein J. Org. Chem. 2015, 11, 233–241, doi:10.3762/bjoc.11.26

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  • product 8 gives the carboxylic acid 9 which on esterification with different long chain alcohols gives various esters 10p–10s. The esters containing the benzyl ether group are deprotected to give the corresponding alcohols (11p–11s). Then they are treated with 4-bromobenzoic acid to give products 12p–12s
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Published 11 Feb 2015

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

  • Thorbjørn Terndrup Nielsen,
  • Catherine Amiel,
  • Laurent Duroux,
  • Kim Lambertsen Larsen,
  • Lars Wagner Städe,
  • Reinhard Wimmer and
  • Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

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  • the 100 nm range of potential biomedical interest. Results and Discussion CPT-dextrans Synthesis The synthesis of CPT-dextrans was achieved in two steps. First azide-modified CPT (N3CPT) was synthesized by esterification with 6-azidohexanoic acid mediated by EDC/DMAP (Scheme 1). TLC showed complete
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Published 21 Jan 2015
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