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Search for "heterocyclization" in Full Text gives 50 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

  • Salvatore V. Giofrè,
  • Santa Cirmi,
  • Raffaella Mancuso,
  • Francesco Nicolò,
  • Giuseppe Lanza,
  • Laura Legnani,
  • Agata Campisi,
  • Maria A. Chiacchio,
  • Michele Navarra,
  • Bartolo Gabriele and
  • Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

Graphical Abstract
  • construction of the spiro[isoxazolidin-isoindolinone] system. The synthetic scheme (Figure 2) exploits the strategy of the 1,3-dipolar cycloaddition of nitrones on the substrate isoindolin-3-methylene-1-one 2, obtained by a recent methodology of a PdI2 catalyzed aminocarbonylation-N-heterocyclization of 2
  • –protein p53-MDM2 interaction. Results and Discussion Chemistry The synthetic scheme towards the construction of the spiro[isoxazolidin-isoindolinone] system 3 starts from isoindolinones 2 which have been synthesized, as reported [35], by Pd-catalyzed aminocarbonylation-N-heterocyclization of 2
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Published 20 Dec 2016

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

  • Artem N. Semakin,
  • Aleksandr O. Kokuev,
  • Yulia V. Nelyubina,
  • Alexey Yu. Sukhorukov,
  • Petr A. Zhmurov,
  • Sema L. Ioffe and
  • Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

Graphical Abstract
  • this case, the primary alkylation adducts might be unstable and undergo heterocyclization reactions (on the synthesis of heterocyclic compounds from azoalkenes and diamines see [54][55][56]). Bishydrazones containing clickable groups (like 3) can be introduced into functional molecules or immobilized
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Published 21 Nov 2016

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

  • Mikhail Yu. Ievlev,
  • Oleg V. Ershov,
  • Mikhail Yu. Belikov,
  • Angelina G. Milovidova,
  • Viktor A. Tafeenko and
  • Oleg E. Nasakin

Beilstein J. Org. Chem. 2016, 12, 2093–2098, doi:10.3762/bjoc.12.198

Graphical Abstract
  • ). Previously we reported about several ways of heterocyclization thereof [15][16][17][18][19][20][21][22][23], including the formation of pyran derivatives [20][21][22][23][24]. Our recent work should be noted individually, we were able to prepare various functionalized pyrano[3,4-c]pyrrole derivatives via
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Published 27 Sep 2016

Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N–O bond-forming cyclization of 2-azidobenzoic acids

  • Daria Yu. Dzhons and
  • Andrei V. Budruev

Beilstein J. Org. Chem. 2016, 12, 874–881, doi:10.3762/bjoc.12.86

Graphical Abstract
  • ], quinolines [9][10][11][12][13] and quinazolines [14][15][16]. Therefore, the search for new methods leading to 2,1-benzisoxazoles is of great interest. For the preparative synthesis of 2,1-benzisoxazoles, in addition to the traditional method based on the reductive heterocyclization of ortho-substituted
  • : 37717). In addition, the structure was confirmed by the alternative synthesis of 2a through the heterocyclization of 2-nitrobenzoic acid [28][29] and X-ray structure analysis [33]. The authors observed that the yields of both 2a and 3a increased with increasing amount of water as nucleophilic solvent in
  • increase in the yield of 3a. In our opinion, this effect of the solvent or base on the yield of 2a may be explained by the formation of 2a through a heterocyclization of 2-azidobenzoate anions. Therefore, the role of the base in the reaction is the in situ generation of the 2-azidobenzoate anion and the
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Published 04 May 2016

Organocatalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors

  • Ming-Liang Zhang,
  • Deng-Feng Yue,
  • Zhen-Hua Wang,
  • Yuan Luo,
  • Xiao-Ying Xu,
  • Xiao-Mei Zhang and
  • Wei-Cheng Yuan

Beilstein J. Org. Chem. 2016, 12, 295–300, doi:10.3762/bjoc.12.31

Graphical Abstract
  • -diones is mainly focused on three-component spiro-heterocyclization reactions [30][31][32]. However, for the catalytic asymmetric transformation, only one example of an aldol reaction of 1H-pyrrole-2,3-diones with ketones has been reported so far (Scheme 1) [33]. Recently, our group developed a chiral
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Published 16 Feb 2016

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

  • Laura G. Sarbu,
  • Lucian G. Bahrin,
  • Peter G. Jones,
  • Lucian M. Birsa and
  • Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

Graphical Abstract
  • was cooled to room temperature and 70% HClO4 and water were added. Filtration and recrystallization of the precipitate gave perchlorates 5a–c as colorless crystals, in 58–81% yield (Scheme 1). The heterocyclization of carbodithioates 4 is supported by their spectral data. The IR spectra revealed the
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Published 15 Oct 2015

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

  • Volodymyr V. Tkachenko,
  • Elena A. Muravyova,
  • Sergey M. Desenko,
  • Oleg V. Shishkin,
  • Svetlana V. Shishkina,
  • Dmytro O. Sysoiev,
  • Thomas J. J. Müller and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

Graphical Abstract
  • ]. Results and Discussion The three-component heterocyclization of 5-amino-3-methylisoxazole (1), salicylaldehyde (2) and N-(2-methoxyphenyl)-3-oxobutanamide (3a) was chosen as a model reaction which was studied by variation of the reaction conditions. First, at room temperature under mechanical stirring for
  • -dihydroisoxazolo[5,4-b]pyridine-5-carboxamide (5a) (Scheme 3) in the reaction mixture when the reaction was performed in n-butanol under conventional heating for 25 min using ytterbium or scandium triflate as the catalysts. Then, it was established that the three-component heterocyclization of aminoisoxazole 1
  • was therefore studied. It was shown that N-(2-ethoxyphenyl)-3-oxobutanamide (3c) behaved under all reaction conditions in the same way as N-(2-methoxyphenyl)-3-oxobutanamide (3a): the three-component heterocyclization in the presence of ytterbium triflate under stirring at room temperature led to the
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Published 17 Dec 2014

Multicomponent reactions in nucleoside chemistry

  • Mariola Koszytkowska-Stawińska and
  • Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

Graphical Abstract
  • three-component process involving the Knoevenagel condensation, the Michael addition and the Thorpe–Ziegler heterocyclization (Scheme 23). Malonitrile acted as the Knoevenagel donor in all cases. The subsequent Michael addition steps involved: cyanothioacetamide [91], 4-hydroxy-6-methylpyridin-2(1H)-one
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Review
Published 29 Jul 2014

Phosphinate-containing heterocycles: A mini-review

  • Olivier Berger and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

Graphical Abstract
  • reaction between bis(trimethylsiloxy)phosphine and the dibromide 50 followed by the esterification of the phosphinic acid using diazomethane (Scheme 21) [32]. The heterocyclization step followed methodology initially introduced by Frost et al [33]. Compound 51 was subsequently converted into the
  • McCormack reaction of conjugated dienes, the sila-Arbuzov reaction of bis(trimethylsiloxy)phosphine with dihalides, etc. continue to be useful. However, novel approaches in both the preparation of acyclic precursors and the reactions to achieve their heterocyclization, have led to more efficient synthesis
  • . Tandem Kabacknik–Fields/C–N cross-coupling reaction. Tandem Kabacknik–Fields/C-P cross-coupling reaction. Heterocyclization via amide formation. Cyclization via reductive amination. H-Phosphinate alkylation. Cyclization through intramolecular Michael addition. Double Arbuzov reaction of bis
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Review
Published 27 Mar 2014

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

  • Suresh Babu Meruva,
  • Akula Raghunadh,
  • Raghavendra Rao Kamaraju,
  • U. K. Syam Kumar and
  • P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

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Published 25 Feb 2014

Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones

  • Benito Alcaide,
  • Pedro Almendros,
  • M. Teresa Quirós and
  • Israel Fernández

Beilstein J. Org. Chem. 2013, 9, 818–826, doi:10.3762/bjoc.9.93

Graphical Abstract
  • heterocyclization reactions to afford 1,3-oxazinan-2-ones 3. To increase the molecular diversity by incorporating more 1,3-oxazin-2-ones in the molecule, compound 2g having two allenic carbamate units was used. Notably, bis(allenic carbamate) 2g also undergoes this interesting transformation to give bis(6-methylene
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Published 26 Apr 2013

Intramolecular carbonickelation of alkenes

  • Rudy Lhermet,
  • Muriel Durandetti and
  • Jacques Maddaluno

Beilstein J. Org. Chem. 2013, 9, 710–716, doi:10.3762/bjoc.9.81

Graphical Abstract
  • this heterocyclization reaction to various nonactivated olefins in a nickel-catalyzed intramolecular base-free Heck-type coupling. Results and Discussion Scope of the reaction We applied the Nickel-catalyzed intramolecular base-free Heck-type coupling to two model substrates, assumed to provide either
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Published 12 Apr 2013

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

  • Eugene S. Gladkov,
  • Katerina A. Gura,
  • Svetlana M. Sirko,
  • Sergey M. Desenko,
  • Ulrich Groth and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

Graphical Abstract
  • polyfunctional aminoazoles that have been studied in heterocyclization reactions [5][6][7][8][20], derivatives of 4-amino-1,2,3-triazole have been less well investigated. There are only a few examples of their heterocyclizations with β-diketones [21], N-cyanomethaneimidates [22], isocyanates [23], chalcones [24
  • contain cross-peaks between pyrimidine NH and spiro-carbon, which is also in good correlation with structure 4. Analogous elucidations allowed the structures of compounds 7 and 9 to be established. Conclusion In summary, two types of heterocyclization reactions involving 4-amino-5-carboxamido-1,2,3
  • [1,2,3]triazolo[5,1-b]quinazoline-3-carboxamides 7 or 9 under all the reactions conditions studied; however, the ultrasound-assisted procedure is the method of choice for this heterocyclization. For all the MCRs studied, changes in the directions of the heterocyclizations were not observed when microwave
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Published 30 Nov 2012

Tricyclic flavonoids with 1,3-dithiolium substructure

  • Lucian G. Bahrin,
  • Peter G. Jones and
  • Henning Hopf

Beilstein J. Org. Chem. 2012, 8, 1999–2003, doi:10.3762/bjoc.8.226

Graphical Abstract
  • a mixture of diastereoisomers, the anti isomer being the major one. The heterocyclization of these compounds provided novel tricyclic flavonoids bearing a 1,3-dithiolium-2-yl ring fused at the 3,4-carbon positions of the benzopyran moiety. Keywords: aminals; benzopyrans; dithiocarbamates
  • flavonoids bearing a 1,3-dithiolium-2-yl ring fused at the 3,4-carbon positions of the benzopyran moiety, utilizing the heterocyclization of corresponding 3-substituted dithiocarbamic flavonones. Results and Discussion The treatment of several dithiocarbamates of type 4 with aminals has been reported to
  • heterocyclization of compounds 6 should, hence, provide new tricyclic fused flavonoids 7 by using an appropriate mixture of acids, as described above (Scheme 1, Table 1). Using a concentrated sulfuric acid/glacial acetic acid (1:3 v/v) mixture [22][23][24] the cyclization of dithiocarbamates 6a–f takes place under
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Published 16 Nov 2012

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

  • Nikolay T. Tzvetkov,
  • Harald Euler and
  • Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

Graphical Abstract
  • intramolecular heterocyclization, formally by dehydration, would afford the 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6-diones III. The success of this route, however, depends on two factors: (i) the preferred regioselectivity of the successive N-alkylation steps for the formation of II; and (ii) the
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Published 20 Sep 2012

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

  • Viktor A. Zapol’skii,
  • Jan C. Namyslo,
  • Armin de Meijere and
  • Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

Graphical Abstract
  • Göttingen, Germany 10.3762/bjoc.8.69 Abstract The nitropolychlorobutadienes 3, 4 are valuable building blocks for various amination and successive heterocyclization products. Nucleophilic substitution reactions of the partially protected, bioactive amines 1, 2 with either vinyl, imidoyl or carbonyl
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Published 23 Apr 2012

Natural product biosyntheses in cyanobacteria: A treasure trove of unique enzymes

  • Jan-Christoph Kehr,
  • Douglas Gatte Picchi and
  • Elke Dittmann

Beilstein J. Org. Chem. 2011, 7, 1622–1635, doi:10.3762/bjoc.7.191

Graphical Abstract
  • -type monooxygenases encoded by the cluster, HctG or HctH, to 2,3-dihydroxyisovaleric acid. Two other NRPS modules contain all the required domains for adenylation and heterocyclization of cysteine, and an FMN-dependent oxidase domain, which is likely involved in thiazole ring formation. The cluster
  • multidrug resistance [59]. The patellamide gene cluster consists of seven genes, expression of which in E. coli leads to the production of the peptides [59]. Heterocyclization of serine, cysteine and threonine, respectively is catalyzed by the heterocyclase PatD [60]. In contrast to other heterocyclases
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Review
Published 05 Dec 2011

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence

  • Dominik Urselmann,
  • Dragutin Antovic and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1499–1503, doi:10.3762/bjoc.7.174

Graphical Abstract
  • access to 1,4-di(hetero)aryl-1,3-butadiynes we reasoned that it should be possible to address the butadiyne functionality towards heterocyclization, again in a one-pot fashion. Here, we communicate the first pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes by virtue of a one-pot
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Published 04 Nov 2011

Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans

  • Verónica Guilarte,
  • M. Pilar Castroviejo,
  • Estela Álvarez and
  • Roberto Sanz

Beilstein J. Org. Chem. 2011, 7, 1255–1260, doi:10.3762/bjoc.7.146

Graphical Abstract
  • ring system, the cyclodehydration of α-aryloxy ketones [29], the Claisen rearrangement of an allyl aryl ether followed by Pd-catalyzed intramolecular oxidative cyclization [30], and the tandem Sonogashira coupling/heterocyclization of 2-halophenols with terminal alkynes [31], are some of the most used
  • Sonogashira coupling and a tandem hydroxylation/heterocyclization reaction. The required o-dihaloanisole derivatives could be prepared by a selective ortho-metallation reaction and subsequent electrophilic quenching with iodine (Scheme 1). Results and Discussion As established in our proposed retrosynthetic
  • heterocyclization. In recent years, the direct hydroxylation of aryl halides has been developed by several groups by using palladium- or copper-catalyzed protocols. Whereas the reactions under copper catalysis work well for aryl iodides [45][46][47][48], the palladium-catalyzed hydroxylation also takes place with
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Published 12 Sep 2011

When gold can do what iodine cannot do: A critical comparison

  • Sara Hummel and
  • Stefan F. Kirsch

Beilstein J. Org. Chem. 2011, 7, 847–859, doi:10.3762/bjoc.7.97

Graphical Abstract
  • matched by electrophilic activation modes, or ii) leads to different product frameworks on treatment with electrophiles. The focus is put on alkyne activation only, while related processes based on the activation of alkenes and allenes are not covered in this review. Review Heterocyclization The vast
  • hydroxy function at the propargylic position, was shown to undergo a cascade involving heterocyclization after activation of the alkyne π-system by the catalysts and a 1,2-alkyl shift (Scheme 2). It was found that this reaction was limited to aryl substituents on the alkyne when the reaction was catalyzed
  • no product formation occurred. In contrast, AuCl3 induced cyclization furnished acyclic products, albeit in low yields. Unlike gold-catalyzed heterocyclization, the NIS-mediated reaction allows access to C4-substituted products and therefore to fully substituted 3(2H)-furanones. It was deduced that a
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Published 22 Jun 2011

A racemic formal total synthesis of clavukerin A using gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes as the key strategy

  • Jae Youp Cheong and
  • Young Ho Rhee

Beilstein J. Org. Chem. 2011, 7, 740–743, doi:10.3762/bjoc.7.84

Graphical Abstract
  • proceeds via the initial heterocyclization intermediate 10 and the subsequently rearranged intermediate 11 (Scheme 3). Notably, when the gold(I)-catalyzed reaction was carried out on a multi-mmol scale, there was no decrease in the yield at the same catalyst loading. With ketone 4 in hand, the final stage
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Published 01 Jun 2011

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

  • Benito Alcaide and
  • Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

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  • Científicas (CSIC), Juan de la Cierva 3, 28006-Madrid, Spain 10.3762/bjoc.7.73 Abstract New gold-catalyzed methods using the β-lactam scaffold have been recently developed for the synthesis of different sized heterocycles. This overview focuses on heterocyclization reactions of allenic and alkynic β-lactams
  • four-membered ring, using the chirality and functionalization of the β-lactam ring as a stereo-controlling element [29][30]. This overview focuses on gold-catalyzed heterocyclization reactions of allenic and alkynic β-lactams which rely on the activation of the allene and alkyne component. The
  • ][40]. The chemodivergent metal-catalyzed heterocyclization of alcohols bearing both an allene and an alkene center has been reported [41]. Starting from 2-azetidinone-tethered ene-allenols 5, FeCl3 was able to catalyze the cyclization chemospecifically in favour of the alkene component to afford
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Review
Published 17 May 2011

Approaches towards the synthesis of 5-aminopyrazoles

  • Ranjana Aggarwal,
  • Vinod Kumar,
  • Rajiv Kumar and
  • Shiv P. Singh

Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25

Graphical Abstract
  • into 5-amino-1-aryl-4-diethoxyphosphoryl-3-halomethylpyrazoles 110. 2,6-Dichloro-4-trifluoromethylphenylhydrazine undergoes this reaction under more drastic conditions, i.e., prolonged refluxing (16–20 h) in carbon tetrachloride (Scheme 31) [73]. Heterocyclization reactions of trifluoromethylcyanovinyl
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Published 09 Feb 2011

A facile synthesis and fungicidal activities of 2-(alkylamino)-5,6-dimethylthieno[2,3-d]pyrimidin- 4(3H)-ones

  • Yang-Gen Hu,
  • Ai-Hua Zheng,
  • Xu-Zhi Ruan and
  • Ming-Wu Ding

Beilstein J. Org. Chem. 2008, 4, No. 49, doi:10.3762/bjoc.4.49

Graphical Abstract
  • carbodiimides, functional groups consisting of the formula N=C=N, able to undergo a plethora of heterocyclization reactions [1][2][3][4][5][6]. At the same time, many heterocycles containing thienopyrimidine system are of great importance for use as potential drugs because of their remarkable biological
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Preliminary Communication
Published 08 Dec 2008

Microwave assisted synthesis of triazoloquinazolinones and benzimidazoquinazolinones

  • Aboul-Fetouh E. Mourad,
  • Ashraf A. Aly,
  • Hassan H. Farag and
  • Eman A. Beshr

Beilstein J. Org. Chem. 2007, 3, No. 11, doi:10.1186/1860-5397-3-11

Graphical Abstract
  • ] Other triazoloquinazolines were obtained from 2'-azidoacetophenone and as well as 2-azidobenzonitrile. [11] Quinazolines were also obtained in moderate yields by an intermolecular reductive N-heterocyclization of 2-nitro-benzaldehydes or 2-nitrophenyl ketones with formamide catalyzed by a combination of
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Published 05 Mar 2007
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