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Search for "carbonitrile" in Full Text gives 62 result(s) in Beilstein Journal of Organic Chemistry.

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

  • Veronika Hladíková,
  • Jiří Váňa and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

Graphical Abstract
  • , it can be concluded that any substituent in position 4 reduces the regioselectivity. The steric hindrance can also affect the ratio of the regioisomers formed. The classical example was described by Yeh et al. [75][76] who performed reactions of 3-(4-ethoxyphenyl)sydnone-4-carbonitrile with various
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Published 05 Jun 2018

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

  • Ranjana Aggarwal and
  • Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Graphical Abstract
  • reported a similar reaction of 5-aminopyrazole 16, arylaldehyde 47 with ethyl cyanoacetate (94) under ultrasound irradiation in presence of p-TSA in water for the synthesis of 3-methyl-6-oxo-4-aryl-4,5,6,7-tetrahydro-4H-pyrazolo[3,4-b]pyridine-5-carbonitrile derivatives 95 (Scheme 27). All the synthesized
  • -(2,4-dichlorophenyl)-1H-pyrazol-5-yl)formimidate (216), in turn was obtained by reaction of 5-amino-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbonitrile (208) with trimethylorthoformate. 4-Amino-1-(2,4-dichlorophenyl)pyrazolo[3,4-d]pyrimidine derivatives 217 were coupled with various carboxylic acids in
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Published 25 Jan 2018

Reactivity of bromoselenophenes in palladium-catalyzed direct arylations

  • Aymen Skhiri,
  • Ridha Ben Salem,
  • Jean-François Soulé and
  • Henri Doucet

Beilstein J. Org. Chem. 2017, 13, 2862–2868, doi:10.3762/bjoc.13.278

Graphical Abstract
  • heteroarenes in the presence of 2 mol % Pd(OAc)2, KOAc as the base in DMA at 90 °C (Scheme 2). The reaction of 2-isopropyl-4-methylthiazole gave the desired product 2 in 82% yield. Conversely, low yields in the target products 3–5 were obtained for the reactions with thiophene-2-carbonitrile, 2-chlorothiophene
  • and 2-pentylthiophene, although complete conversions of 2-bromoselenophene were observed. A similar result was obtained for the reaction with 1-phenylpyrrole. Reactions performed at a higher temperature with thiophene-2-carbonitrile, 2-chlorothiophene afforded 3 and 4 in slightly lower yields
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Published 22 Dec 2017

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

  • Jan Podlesný,
  • Lenka Dokládalová,
  • Oldřich Pytela,
  • Adam Urbanec,
  • Milan Klikar,
  • Numan Almonasy,
  • Tomáš Mikysek,
  • Jaroslav Jedryka,
  • Iwan V. Kityk and
  • Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

Graphical Abstract
  • and its final cross-coupling reactions (Scheme 1). The construction of the DPP central scaffold 6 was accomplished by a well-known reaction between thiophene-2-carbonitrile and dimethyl succinate in the presence of sodium tert-amylalcoholate generated in situ [32]. The reaction provided 6 with a high
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Published 08 Nov 2017

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

  • Maryna V. Murlykina,
  • Maryna N. Kornet,
  • Sergey M. Desenko,
  • Svetlana V. Shishkina,
  • Oleg V. Shishkin,
  • Aleksander A. Brazhko,
  • Vladimir I. Musatov,
  • Erik V. Van der Eycken and
  • Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

Graphical Abstract
  • with 2-amino-1,3,4-thiadiazoles [71][83][84][89][90], 2-aminoimidazoles [71][72][91][92], 2-aminoxazoles [71] and 1,2,5-oxadiazole-3,4-diamine [93] with the formation of imidazoazoles. Among the pyrazoles only 5-amino-3-methylpyrazole, 5-aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4
  • -binucleophile, acid – catalyst). Literature data indicate [14][25][59][97][98][99][100][101] that 5-aminopyrazoles bearing in the fourth position electron-withdrawing substituents like carboxamide, carboxylate or a carbonitrile group, posses chemical properties being different from other 5-aminopyrazoles but
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Published 31 May 2017

Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

  • Anna Wrona-Piotrowicz,
  • Marzena Witalewska,
  • Janusz Zakrzewski and
  • Anna Makal

Beilstein J. Org. Chem. 2017, 13, 1032–1038, doi:10.3762/bjoc.13.102

Graphical Abstract
  • , although substitution at the 1-position prevails. For ethoxycarbonyl isothiocyanate, apart from the 1-substituted thioamide, 1,8-disubstituted thioamide and 2,7-di-tert-butylpyrene-1-carbonitrile are formed (especially at longer reaction times). Keywords: amide; Friedel–Crafts; isocyanate; isothiocyanate
  • data of other synthesized thioamides, see Supporting Information File 1). 2,7-Di-tert-butylpyrene-1-carbonitrile (5). Yellow solid. Mp 176–177 °C; 1H NMR (600 MHz, CDCl3) δ 8.50 (d, J = 9.0 Hz, 1H), 8.30 (d, J = 1.2 Hz, 1H), 8.28 (d, J = 1.2 Hz, 1H), 8.18 (d, J = 9.6 Hz, 1H), 8.17 (s, 1H), 8.14 (d, J
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Published 29 May 2017

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

  • Gabriel P. Costa,
  • Natália Seus,
  • Juliano A. Roehrs,
  • Raquel G. Jacob,
  • Ricardo F. Schumacher,
  • Thiago Barcellos,
  • Rafael Luque and
  • Diego Alves

Beilstein J. Org. Chem. 2017, 13, 694–702, doi:10.3762/bjoc.13.68

Graphical Abstract
  • -(phenylselanylmethyl)-1,2,3-triazole A (Se-TZ) demonstrated an antidepressant-like effect (Figure 1) [60]. In another example, 5-phenyl-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile B (Se-TZCN) was reported to exhibit antioxidant activities in different in vitro assays (Figure 1) [36]. Selenanyl-quinone
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Published 11 Apr 2017

Synthesis of 1-indanones with a broad range of biological activity

  • Marika Turek,
  • Dorota Szczęsna,
  • Marek Koprowski and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

Graphical Abstract
  • -iodoaryl)propanonitriles 193 leading to the formation of the nitrile 195 as a byproduct (Scheme 55). Cyclization of 3-phenylnaphtalene-2-carbonitrile (199) in the presence of polyphosphoric acid gave 1-indanone 200 in 76% yield. The nitrile 199 was obtained from benzaldehyde 196 as a result of sequencial
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Published 09 Mar 2017

The reductive decyanation reaction: an overview and recent developments

  • Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

Graphical Abstract
  • anhydrous NiCl2 with NaBH4 in t-BuOH, iPrOH or n-butanol, the reactions are then performed upon bubbling of hydrogen at atmospheric pressure through the reaction mixture (Scheme 13). The reductive decyanation of 2-hydroxyadamantane-2-carbonitrile is successful by this method and yields alcohol 32 [85]. For
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Published 13 Feb 2017

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
  • presence thereof, but all acids promote only the iminolactone decyclization process without traces of lactone derivative 4 (Table 2). It is also important to note that during the reaction pathway (Scheme 3) a carbonyl-assisted carbonitrile hydration effect (CACHE) was occured. The carbonyl group, through
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Published 27 Sep 2016

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

  • Jacob R. Hauser,
  • Hester A. Beard,
  • Mary E. Bayana,
  • Katherine E. Jolley,
  • Stuart L. Warriner and
  • Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

Graphical Abstract
  • -carbonitrile (13) [19] A solution of NaCN (2.40 g, 48.97 mmol) in H2O (100 mL) was added slowly to a stirred solution of 2-chloro-6-nitro-1,3-benzothiazole (6, 10.0 g, 46.59 mmol) and DABCO (748 mg, 6.99 mmol) in MeCN (1000 mL). The reaction mixture was stirred at room temperature for 24 h. Excess cyanide was
  • MHz, CDCl3) δ 8.96 (d, J = 2.1 Hz, 1H, CH-7), 8.52 (dd, J = 9.1, 2.1 Hz, 1H, CH-5), 8.38 (d, J = 9.1 Hz, 1H, CH-4); 13C NMR (125 MHz, CDCl3) δ 155.5 (C-6), 147.4 (C-7a), 141.9 (C-2), 135.7 (C-3a), 126.2 (CH-4), 123.2 (CH-5), 118.7 (CH-7), 112.1 (C≡N). 6-Amino-1,3-benzothiazole-2-carbonitrile (8) [21
  • ] Iron powder (68.05 g, 1218.55 mmol) was added to a suspension of 6-nitro-1,3-benzothiazole-2-carbonitrile (13, 5.00 g, 24.37 mmol) in acetic acid (500 mL). The reaction mixture was stirred at room temperature for 24 h, diluted with water (1 L) and unreacted iron was removed by filtration through celite
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Published 13 Sep 2016

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

  • Roman Yu. Peshkov,
  • Elena V. Panteleeva,
  • Wang Chunyan,
  • Evgeny V. Tretyakov and
  • Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

Graphical Abstract
  • )pentane – but the reaction mixture contained traces of compounds with molar masses of 325 and 352 (<1.5% according to GC–MS), which can be attributed to 4'-(5-phenylpentyl)-[1,1'-biphenyl]-4-carbonitrile and 4'-(5-(1-cyanocyclohexa-2,5-dien-1-yl)pentyl)-[1,1'-biphenyl]-4-carbonitrile, respectively. The
  • consideration of the present paper. In this context, 2,6-difluorobenzonitrile (2g) and 4'-methylbiphenyl-2-carbonitrile (2h) [25] (which can be considered as benzonitrile, substituted with a p-tolyl fragment at the 2 position) show generally the same behavior as all the explored benzonitriles. The result
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Published 25 Jul 2016

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

  • Madhuri Vangala and
  • Ganesh P. Shinde

Beilstein J. Org. Chem. 2015, 11, 2289–2296, doi:10.3762/bjoc.11.249

Graphical Abstract
  • , the reaction of 5a (0.2 g, 0.415 mmol) was performed at different concentrations (2.5, 5, 10, and 15 equiv) of cyclohexane carbonitrile (Table 1, entry 3) in dry toluene using TMSOTf (1 equiv) at 0 °C to rt under N2 atmosphere. A complex mixture of products was obtained with 2.5 equiv and 5 equiv of
  • nitrile, along with trace amounts of product. Using 10 equiv of cyclohexane carbonitrile gave moderate yield of product 8a along with the formation of di-D-fructose dianhydride or spiroketals [49] as the side product. Finally, 15 equiv of nitrile served best for this transformation providing
  • the β-orientation, leading to a high stereoselectivity. Finally, due to the widespread applicability of chiral oxazolines, the synthesis of fructose-derived spirooxazolines was examined on a multigram scale. For example, the reaction of 5a (1.2 g, 2.49 mmol) with cyclohexane carbonitrile (15 equiv) in
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Published 24 Nov 2015

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

  • Mingxing Liu,
  • Jiarong Li,
  • Hongxin Chai,
  • Kai Zhang,
  • Deli Yang,
  • Qi Zhang and
  • Daxin Shi

Beilstein J. Org. Chem. 2015, 11, 2125–2131, doi:10.3762/bjoc.11.229

Graphical Abstract
  • -carbonitrile with amides [18][19][20][21], carboxylic acids [22][23][24], amidines [25][26], nitriles [27][28], ketones [29][30] and halohydrocarbon [31], the cyclization of 5-aminopyrazole-4-carboxamides with amides [32], ureas [33][34][35][36], esters [37][38][39] and acyl chloride [40], and the reaction of
  • aminopyrazoles and amides [41][42]. In our previous studies, dihydropyrimidinone was synthesized through the condensation of 5-aminopyrazole-4-carbonitrile and ketones [29][30]. 5-Aminopyrazole-4-carbonitrile was prepared from the reaction of ethoxymethylenemalononitrile with phenylhydrazine in a step-wise
  • , this is a novel methodology for the synthesis of pyrazolo[3,4-d]pyrimidines by the reaction of hydrazines, methylenemalononitriles, aldehydes and alcohols. During the preparation of this manuscript, Liu et al. reported the synthesis of pyrazolo[3,4-d]pyrimidines from 5-aminopyrazole-4-carbonitrile [48
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Published 06 Nov 2015

Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines

  • Ya Lin Tnay,
  • Gim Yean Ang and
  • Shunsuke Chiba

Beilstein J. Org. Chem. 2015, 11, 1933–1943, doi:10.3762/bjoc.11.209

Graphical Abstract
  • cleavage of N–H ketimines. Treatment of N–H ketimines having an α-sp3 hybridized carbon under Cu-catalyzed aerobic reaction conditions resulted in a radical fragmentation with C–C bond cleavage to give the corresponding carbonitrile and carbon radical intermediate. This radical process has been applied for
  • of biaryl N–H ketimines under copper-catalyzed aerobic reaction conditions, aiming at the synthesis of 6-membered azaspirocycles such as 3a’ from carbonitrile 1a having a quaternary sp3-hybridized carbon center at its α-position. The reaction of p-tolylmagnesium bromide (2a) to carbonitrile 1a
  • 1aa most likely via the corresponding iminyl radical, that undergoes radical fragmentation to afford the corresponding C-radical and carbonitrile 5a [55]. Thus, it is deduced that oxaspirocyclohexadienone 3a was formed through oxygenation of the putative C-radical. Moreover, in this transformation
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Published 19 Oct 2015

Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate

  • Piotr Wałejko,
  • Michał Dąbrowski,
  • Lech Szczepaniak,
  • Jacek W. Morzycki and
  • Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 1893–1901, doi:10.3762/bjoc.11.204

Graphical Abstract
  • ROCM reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-en-2-carbonitrile (1 and 2, respectively) with allyl acetate (3) or allyl alcohol (4) catalyzed by several commercially available ruthenium catalysts ([Ru]1–6, Figure 1). To the best of our knowledge there is no example of a ROCM reaction of 7
  • ) H-2” and C-5, H-5 and C-2”, H-2 and C-3’, H-2 and C-2’; RI: 1667 (tR = 37.34 min); TOF MS ES+: 244 [M + Na]+; HRMS m/z: [M + Na]+ calcd for C12H15NO3Na: 244.0944; found: 244.0943. 5-((E)-3’-Hydroxyprop-1’-en-1’-yl)-2-vinyltetrahydrofuran-3-carbonitrile (8E). 1H NMR (CDCl3, δ, ppm) 5.98–5.83 (m, 2H
  • ; found: 202.0848. 5-((Z)-3'-Hydroxyprop-1'-en-1'-yl)-2-vinyltetrahydrofuran-3-carbonitrile (8Z). 1H NMR (CDCl3, δ, ppm) 5.86–5.77 (m, 3H, H-1’, 2’ and 1”), 5.51, 5.46, 5.34, 5.31 (4 x ~s, 2H, H-2”), 4.91–4.80 (m, 1H, H-2), 4.46–4.43 (m, 1H, H-5), 4.31–4.23 (m, 2H, H-3’), 2.85–2.80 (m, 1H, H-3), 2.48–2.42
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Published 13 Oct 2015

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

  • Sandrina Oliveira,
  • Dulce Belo,
  • Isabel C. Santos,
  • Sandra Rabaça and
  • Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

Graphical Abstract
  • -tetrathiafulvalene (CNB-EDT-TTF), was obtained in high yield, by a cross-coupling reaction with triethyl phosphite between 2-thioxobenzo[d][1,3]dithiole-5-carbonitrile and 5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-one. This new donor was characterized namely by single crystal X-ray diffraction, cyclic
  • route to prepare non-symmetrically substituted TTF derivatives by cross coupling of two different 1,3-dichalcogenole-2-chalconegones [14][15], involving the coupling between 2-thioxobenzo[d][1,3]dithiole-5-carbonitrile (1) [16] and 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one (2) in 1:1.1 ratio in
  • ]dithiole-5-carbonitrile (1, 1 mmol, 0.21 g) and 5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-one (2, 1.1 mmol, 0.23 g) were heated up to 130 °C under N2 at reflux for 4 h, which led to a formation of an orange precipitate. The precipitate was filtered and washed with cold methanol and dried under vacuum
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Published 03 Jun 2015

Palladium-catalyzed 2,5-diheteroarylation of 2,5-dibromothiophene derivatives

  • Fatma Belkessam,
  • Aidene Mohand,
  • Jean-François Soulé,
  • Abdelhamid Elias and
  • Henri Doucet

Beilstein J. Org. Chem. 2014, 10, 2912–2919, doi:10.3762/bjoc.10.309

Graphical Abstract
  • was expected, as they are known to be less reactive than thiazole derivatives [44]. Moderate yields for 5 and 6 were obtained starting form thiophene-2-carbonitrile and ethyl thiophene-2-carboxylate, respectively in the presence of 2 mol % PdCl(C3H5)(dppb) catalyst due to the formation of unidentified
  • with 2-methylthiophene and thiophene-2-carbonitrile also afforded the desired products 24 and 25 in good yields. A decreased yield of 41% for 26 was obtained with thiophene as coupling partner, whereas, 1-methylpyrrole gave 27 in 74%. Coupling of 1a with methyl 2-methylfuran-3-carboxylate afforded 28
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Published 09 Dec 2014

Facile synthesis of 1H-imidazo[1,2-b]pyrazoles via a sequential one-pot synthetic approach

  • András Demjén,
  • Márió Gyuris,
  • János Wölfling,
  • László G. Puskás and
  • Iván Kanizsai

Beilstein J. Org. Chem. 2014, 10, 2338–2344, doi:10.3762/bjoc.10.243

Graphical Abstract
  • Abstract 5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke–Blackburn–Bienaymé reaction (GBB reaction). Besides the
  • ) inputs (Scheme 1). The transformations of either the 5-aminopyrazoles [28][29], or their 4-substituted ethoxycarbonyl [7][30][31][32] and carbonitrile [28][33][34][35][36] analogues via the GBB-3CR have not been appreciably examined so far. In the relevant literature [7][28][29][31][32][33], the products
  • -aminopyrazole-4-carbonitrile (1a), p-tolualdehyde (2a) and tert-butyl isocyanide (3a) in order to elucidate the structure of the product and investigate the regioselectivity. The synthesis of 5-aminopyrazole-4-carbonitrile (1a) was based on a literature method [43][44]. A single product was observed in a yield
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Published 08 Oct 2014

Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism

  • Denisa Tarabová,
  • Stanislava Šoralová,
  • Martin Breza,
  • Marek Fronc,
  • Wolfgang Holzer and
  • Viktor Milata

Beilstein J. Org. Chem. 2014, 10, 752–760, doi:10.3762/bjoc.10.70

Graphical Abstract
  • are shown in Scheme 3. It is well known that the reaction of hydrazine hydrate with alkoxymethylidenemalononitrile affords 3-amino-1H-pyrazole-4-carbonitrile (5a) [8][9][10][11][12][13]. Eight tautomeric forms of 5a could theoretically be expected (Figure 1). Five of these tauromeric forms carry an
  • -carbonitrile (δ C3 139.8 ppm, δ C4 72.1 ppm, δ C5 151.4 ppm). Thus, it can be assumed that isomer 5aA2 provides a marked contribution to the tautomeric mixture. However, NOE measurement between the pyrazole-CH and pyrazole NH hints at the simultaneous presence of species 5aA1, where the protons involved are
  • -1H-pyrazole-4-carbonitrile (5a), alkyl 3-hydroxypyrazole-4-carboxylates 5b, 5c or 1-(3-methyl-1H-pyrazol-4-yl)ethanone (5d). The reversed addition of the enol ethers to hydrazine hydrate the formation of bis-enehydrazine 6 product was observed in two tautomeric forms: with symmetrical and
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Published 01 Apr 2014

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

  • Richard J. Ingham,
  • Claudio Battilocchio,
  • Joel M. Hawkins and
  • Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

Graphical Abstract
  • –Ponndorf–Verley reductions [22] and Oppenauer oxidations [23] where zirconia activation is required). In fact, it seems that the extent of hydration of pyrazine-2-carbonitrile is proportional to the initial water content of the zirconium catalyst. To confirm this hypothesis, we ran a control experiment in
  • 42689) can be plugged directly into the RPi or through the USB hub for serial communication. Two step approach to piperazine-2-carboxamide via hydrolysis followed by reduction. (a) Retrosynthesis and (b) catalytic transformations. Heterogeneous hydration of pyrazine-2-carbonitrile with hydrous zirconia
  • . FlowIR™ profile for the reactor output after hydration of pyrazine-2-carbonitrile using hydrous zirconia. Both peaks correspond to the product. A solution of the nitrile in ethanol (0.06 M) was passed at 0.1 mL min−1 through the column, heated to 100 °C. The response rises after approximately one column
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Published 12 Mar 2014

Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis

  • Frank Hahn,
  • Nadine Kandziora,
  • Steffen Friedrich and
  • Peter F. Leadlay

Beilstein J. Org. Chem. 2014, 10, 634–640, doi:10.3762/bjoc.10.55

Graphical Abstract
  • , anticancer and anti-angiogenesis activities, which are probably caused by the inhibition of threonyl-tRNA synthetase and apoptosis induction by caspase activation [1][2][3][4]. It bears several unusual structural elements like a cyclopentane ring and a carbonitrile (Figure 1a), which are built-up by
  • unconventional biosynthesis mechanisms [5][6]. The carbonitrile for example is probably formed by allylic oxidation of the 12-methyl group in 12-desnitrile-12-methylborrelidin to the corresponding aldehyde and transamination to the amine followed by oxidation [6]. In the course of our studies on borrelidin
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Published 11 Mar 2014

The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

  • Mrinal K. Bera,
  • Moisés Domínguez,
  • Paul Hommes and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

Graphical Abstract
  • diphenic acid (12) in combination with methoxyallene (7), pivalonitrile (9) and thiophene-2-carbonitrile (10) in the three-component reaction (Scheme 2). Gratifyingly we were able to isolate the expected bis(β-ketoenamides) 13–15 in reasonable yields of 15–28%. Taking the number of individual steps into
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Published 13 Feb 2014

Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

  • Moustafa Sherief Moustafa,
  • Saleh Mohammed Al-Mousawi,
  • Maghraby Ali Selim,
  • Ahmed Mohamed Mosallam and
  • Mohamed Hilmy Elnagdi

Beilstein J. Org. Chem. 2014, 10, 141–149, doi:10.3762/bjoc.10.11

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  • , P.O. Box 83523, Qena, Egypt 10.3762/bjoc.10.11 Abstract Novel routes for the preparation of 2-amino-4H-pyran-3-carbonitrile 9, amino-arylbenzoic acid ester derivatives 13a,b, 2-aminotetrahydro-4H-chromene-3-carbonitrile 18, 3-amino-4-cyanotetrahydronaphthalene-2-carboxylic acid ester 26 and 4-amino
  • the products. Finally, these compounds were used for the efficient synthesis of 6-amino-5-cyanonicotinic acid ester derivatives 31a,b, ethyl 4-amino-5H-pyrano[2,3-d]pyrimidine-6-carboxylates 33a,b, 4-amino-6H-pyrrolo[3,4-g]quinazoline-9-carbonitrile 39, and 1,7-diamino-6-(N'-hydroxycarbamimidoyl)-3
  • malononitrile with benzaldehyde and cyclic ketones [11] (Scheme 2). In contrast, MW-irradiation-promoted reactions of ketones, aldehydes and malononitrile are known to afford polysubstituted benzenes 3 (Scheme 3) [12]. Elnagdi et al. reported [13] that reaction of alkyl azenyl carbonitrile with arylidene
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Published 14 Jan 2014

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles

  • Adam Trawczyński,
  • Robert Bujok,
  • Zbigniew Wróbel and
  • Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2013, 9, 934–941, doi:10.3762/bjoc.9.107

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  • ketone 5d upon reduction with SnCl2 cyclized to pyrrolo[3,2-f]quinoline-9-carbonitrile 7 [17]. The removal of the benzyloxymethyl group from 1-(benzyloxymethyl)pyrrolo[3,2-e]indoles by catalytic hydrogenation has been described by Macor [6]. The hydroxy group from the N-hydroxypyrrole fragment can be
  • -3,6-dihydropyrrolo[3,2-e]indole-1-carbonitrile (6b). Yellow crystals; mp 194–196 °C; 1H NMR (500 MHz, DMSO-d6) δ 2.53 (d, J = 0.7 Hz, 3H), 2.74 (s, 3H), 4.85 (s, 2H), 5.74 (s, 2H), 6.75 (br s, 1H), 7.24–7.29 (m, 3H), 7.30–7.34 (m, 2H), 7.35 (d, J = 9.1 Hz, 1H), 7.76 (d, J = 9.1 Hz, 1H), 12.49 (br s
  • -dimethylpropionyl)-3-hydroxy-7-methyl-3,6-dihydropyrrolo[3,2-e]indole-1-carbonitrile (6c). Brown solid; mp 155–157 °C; 1H NMR (500 MHz, DMSO-d6) δ 1.32 (s, 9H), 2.52 (d, J = 0.8 Hz, 3H), 4.47 (s, 2H), 5.73 (s, 2H), 6.68 (br s, 1H), 7.24–7.35 (m, 6H), 7.67 (d, J = 9.0 Hz, 1H), 12.50 (br s, 1H); 13C NMR (125 MHz
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Published 15 May 2013
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