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Search for "nitrile" in Full Text gives 261 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 2023

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO2F2)

  • Xian-Lin Chen and
  • Hua-Li Qin

Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68

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  • the construction of a range of δ-olefin-containing aliphatic nitriles with (E)-configuration selectivity. This new method features wide substrate scope, mild conditions, and direct N–O activation. Keywords: direct N–O activation; E-selectivity; nitrile synthesis; ring-opening cross-coupling; sulfuryl
  • fluoride; SO2F2; Introduction As an important functional group in organic molecules, the nitrile group is commonly present in functional materials [1][2], nanoscale drug carriers [3][4][5], biologically valuable molecules and drugs (Scheme 1) [6][7]. There are over 70 nitrile-containing drugs approved by
  • the FDA for various indications and more than 140 additional nitrile-containing leads in clinical investigation [8]. Looking into changing the physicochemical properties, in the field of drug discovery, it is important to explore solutions to introduce nitrile groups into a molecule for enhancing the
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Published 22 Jun 2023

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

  • Lukáš Marek,
  • Jiří Váňa,
  • Jan Svoboda and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

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  • with a α-haloketone or α-haloester II. The initially formed α-thioiminium salt III can undergo either a base-catalyzed elimination to give nitrile X and thiol IX [10][11][12] or cyclization to give a thiazole XIII or thiazolone XI depending on the substituent at the carbonyl group Y. Both side
  • reaction pathway opens that involves either the E2 or E1cB-like mechanism to give the corresponding nitrile X and thiolate IX, which can be further alkylated with an excess of α-halogen component to give a symmetrical sulfide. Only in very few cases when the starting α-thioiminium salt III contains an
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Published 09 Jun 2023

Strategies in the synthesis of dibenzo[b,f]heteropines

  • David I. H. Maier,
  • Barend C. B. Bezuidenhoudt and
  • Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

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  • '-dibromostilbenes 61 by means of a double Buchwald–Hartwig amination gave yields between 62% and 96% using aniline as the amine reactant (Scheme 13). The reaction proved to be compatible with both aromatic and aliphatic amines and the reaction time varied between 11 and 24 hours. Fluoro, chloro, nitrile, alkyl, and
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Published 22 May 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

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Published 24 Apr 2023

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

  • Jorge de Lima Neto and
  • Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

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  • ] between halide 37 and phenol 38 leading to the formation of diaryl ether 39, which was subjected to a regioselective iodination reaction to give compound 40. Conversion of the nitrile in compound 40 into the corresponding aldehyde 41 followed by Z-selective Still–Gennari olefination gave the cis α,β
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Published 29 Mar 2023

Group 13 exchange and transborylation in catalysis

  • Dominic R. Willcox and
  • Stephen P. Thomas

Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28

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  • pathways (Scheme 9), where two pathways were operative. The hydroboration of the nitrile 36 gave a borylimine 37, which underwent a second hydroboration with the borane catalyst to give a diborylamine 38. Double B‒N/B‒H transborylation of the diborylamine 38 with HBpin regenerated the catalyst and gave the
  • and HBcat (Scheme 27) [122]. The precatalyst ([Fe(CH3CN)6][cis-Fe(CO)4(InCl3)2]) was activated in situ with HBpin to give ClBpin and HInCl2 107 by In‒Cl/B‒H exchange. The indium hydride 107 underwent hydroelementation of an iron-coordinated nitrile 108, to give an indylimine iron complex 109, which
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Published 21 Mar 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

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  • reduction of the amide using Wilkinson’s catalyst provided diastereoisomeric indole 131. Careful manipulation of the nitrile and alcohol side chains allowed selective cyclizations to the nitrogen atom of the indole core to conclude the total syntheses of 132–134. Samarium diiodide-mediated reductive
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Published 02 Jan 2023

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

  • Filip Meger,
  • Alexander C. W. Kwok,
  • Franziska Gilch,
  • Dominic R. Willcox,
  • Alex J. Hendy,
  • Kieran Nicholson,
  • Andrew D. Bage,
  • Thomas Langer,
  • Thomas A. Hunt and
  • Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

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  • of a double B–N/B–H transborylation mechanism. Keywords: boron; catalysis; hydroboration; nitrile; transborylation; Introduction Primary amines are prevalent throughout organic synthesis, finding regular application in materials chemistry, pharmaceuticals, and agrochemicals (Scheme 1a) [1][2][3
  • ]. Traditionally, the reduction of nitriles to primary amines relied on stoichiometric hydride reagents [4]. Current catalytic methods for nitrile reduction, hydrogenation [5][6] or hydroboration [7][8], generally rely on metal catalysts, designer ligands, forcing reaction conditions (such as elevated temperatures
  • and pressures) or lack extensive functional group tolerance. In particular, catalysed nitrile hydroboration strategies are still underdeveloped compared with hydrogenation, but offer a nascent alternative to this established field. The pursuit of sustainable chemical transformations has driven
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Published 26 Sep 2022

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

  • Shang-Feng Yang,
  • Pei Li,
  • Zi-Lin Fang,
  • Sen Liang,
  • Hong-Yu Tian,
  • Bao-Guo Sun,
  • Kun Xu and
  • Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

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  • protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically
  • 3v in 23% yield. In addition to β-keto esters, other active methylene derivatives, including β-ketoamide, β-keto nitrile and β-keto sulfone were also suitable coupling partners with relatively lower yields (3w–y) and most of the starting materials were recovered. The method could also be applied to
  • performed in an undivided cell with NH4I as the mediator and cheap graphite plate as the working electrode. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diones proved to be compatible with the protocol. Since external oxidants and
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Published 15 Sep 2022

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

  • Alexander S. Filatov,
  • Olesya V. Khoroshilova,
  • Anna G. Larina,
  • Vitali M. Boitsov and
  • Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

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  • -2-ene-1-carboxylic acid 2f–i. The amide 2f and nitrile 2g [34] were found to be less active dipolarophiles towards the azomethine ylide 1 than hydrocarbons 2a–e. As a result, the corresponding cycloadducts 3f and 3g were obtained in moderate yields (58% and 55%, respectively) as single diastereomers
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Published 29 Jun 2022

An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates

  • Timur O. Zanakhov,
  • Ekaterina E. Galenko,
  • Mikhail S. Novikov and
  • Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2022, 18, 738–745, doi:10.3762/bjoc.18.74

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  • processes. To evaluate the scope of the disclosed reaction a set of isoxazoles 1 was prepared using approaches shown in the Scheme 3 and Scheme 4. Isoxazoles 11a–f were prepared by cycloaddition of nitrile oxides, generated from N-hydroxyimidoyl chlorides 7a–f, to propargyl halides [29], followed by the
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Published 23 Jun 2022

Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides

  • Md Imran Hossain,
  • Md Imdadul H. Khan,
  • Seong Jong Kim and
  • Hoang V. Le

Beilstein J. Org. Chem. 2022, 18, 446–458, doi:10.3762/bjoc.18.47

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  • Agriculture, Agricultural Research Service, University of Mississippi, Mississippi 38677, USA 10.3762/bjoc.18.47 Abstract Herein we report a method for the synthesis of 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature via a [3 + 2]-cycloaddition of nitrile oxides and
  • cycloaddition of alkynes and nitrile oxides performed in organic solvents at elevated temperatures (Figure 1) [11][12][13][14][15][16]. In this method, while 3,5-disubstituted isoxazoles can be accessed from terminal alkynes, 3,4,5-trisubstituted isoxazoles require a high degree of substitution on non-terminal
  • needed to be synthesized independently [23]. While ruthenium(II) and palladium catalysts are useful, they are expensive and environmentally unfriendly. The dehalogenation of hydroximoyl chlorides in the presence of a strong base to generate nitrile oxides and a follow-up cycloaddition with 1,3-diketones
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Published 22 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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  • based on Diels–Alder reactions of cyclopentadiene with alkynes [13][14][15][16][17][18][19][20][21][22][23]. However, since this synthetic route requires strongly electrophilic alkynes, its scope is limited to products that contain at least one electron-acceptor group, such as an ester, a nitrile or
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Published 01 Apr 2022

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

  • Irina Kuznetcova,
  • Felix Bacher,
  • Daniel Vegh,
  • Hsiang-Yu Chuang and
  • Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

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  • further reacted with potassium cyanide to yield nitrile 12 [27]. Saponification of the nitrile was performed by exploiting the Pinner reaction with saturated HCl gas in methanol. This led to methyl indol-2-ylacetate (13) in 83% yield [28]. The hydrolysis of ester 13 was performed in the presence of
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Published 26 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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  • -oxazoles are: the 1,3-dipolar cycloaddition of alkenes and alkynes with nitrile oxides, and the reaction of a three-carbon atom component, such as a α,β-unsaturated ketone or a 1,3-diketone with hydroxylamine hydrochloride [33]. Recently, Rosa et al. reported a useful procedure for the synthesis of various
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Published 12 Jan 2022

Recent advances and perspectives in ruthenium-catalyzed cyanation reactions

  • Thaipparambil Aneeja,
  • Cheriya Mukkolakkal Abdulla Afsina,
  • Padinjare Veetil Saranya and
  • Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 37–52, doi:10.3762/bjoc.18.4

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  • corresponding imine. Finally, oxidative dehydrogenation results in the formation of the nitrile. Conclusion This review summarizes the recent progress in ruthenium-catalyzed cyanation reactions. Due to the wide application of nitrile compounds in pharmaceutical and biological fields, cyanation reactions have
  • of arenes and heteroarenes with high functional group tolerance. Some of the suggested methods utilized photoredox catalysts and thus offer new avenues towards greener and economical nitrile synthesis. In spite of these advancements, the use of toxic cyanating agents like NaCN in almost all the
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Published 04 Jan 2022

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

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  • thermal conditions or through the Fe redox cycle, can abstract the aldehydic hydrogen to form the acyl radical 71. Subsequent radical addition to the alkene 68 to form 72 followed by cyclization with the nitrile affords the iminyl radical 73 which can abstract a hydrogen atom to form the more stable imine
  • compatible with the nucleophilic capture process. In the proposed mechanism, the α-hydrogen of the alkyl nitrile is deprotonated to form an organosilver species which undergoes SET oxidation with Ag(I) to afford the alkyl radical. Next, the α-cyanocarbon radical can add across the styrene derivative
  • the carboamination of activated alkenes 115 with alkyl diacyl peroxides 163 and acetonitrile (Scheme 34) [136]. Their efficient protocol featured a broad substrate scope, including diversely functionalized styrene derivatives, various alkyl diacyl peroxides, and a few different nitrile solvents which
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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

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  • found to be very low due to a reductive replacement of the fluoro atoms of the benzyl ring during the reduction of the nitrile with LiAlH4. Only a small amount (5% yield) of the desired compound was isolated. Also, a reductive replacement was observed during the conversion of 12h, yielding the
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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

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  • cycloaddition reactions and also serves as a precursor for the generation of important functional groups like amines, aldehydes, ketones and carboxylic acids. Even though the nitrile functional group is prevalent in the transformation into different functional groups, the synthetic approaches that incorporate
  • 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

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

  • Ilya A. P. Jourjine,
  • Lukas Zeisel,
  • Jürgen Krauß and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

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  • secondary and tertiary amines, amides/lactams/carbamates, and nitrile. The test reactions were monitored by thin-layer chromatography (TLC) and, where deemed necessary, results were further verified by GC–MS. The reagents employed encompassed tritylium tetrafluoroborate [50], H2O2/HBr [42], ceric ammonium
  • beneficial effect here. Notably, the reaction of nitrile 2m did not yield any target compound 3 (Table 1, entry 13). Substituted 2-phenylbenzonitriles have been reported to yield fluorenones in good yields under Pd-Ag-catalysis in previous research efforts [54]. At this point we concluded that out of all
  • existing literature [38] and further investigations may thus give way to new synthetic possibilities in natural products synthesis in cases access to or cyclization of benzylamine moieties appears practical. Moreover, aldehyde precursors may not only be less readily available than nitrile precursors but
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Published 02 Nov 2021

AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

  • Yelizaveta Gorbunova,
  • Dmitry S. Ryabukhin and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2021, 17, 2663–2667, doi:10.3762/bjoc.17.180

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  • –C≡N) are versatile building blocks in organic synthesis for the preparation of a plethora of functionalized compounds and heterocycles. The presence of conjugated acetylene and nitrile bonds in these compounds leads to an enhancement of reactivity of both functional groups. Thus, propynenitriles
  • take part in electrophilic [1][2] and nucleophilic [3][4][5][6] addition reactions onto the acetylene bond leading to various substituted nitriles. Reactions onto both acetylene and nitrile groups are widely used for the construction of various heterocyclic systems [7][8][9][10][11][12][13][14][15
  • ) through the regioselective hydroarylation of the carbon–carbon double bond. In TfOH, the reactions proceed further to 3-arylindanones, as products of the intramolecular aromatic acylation of the 3,3-diarylpropanenitriles by the electrophilically activated nitrile group [16][17]. Based on this study and
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Published 01 Nov 2021

Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction

  • Dušan Đ. Škorić,
  • Olivera R. Klisurić,
  • Dimitar S. Jakimov,
  • Marija N. Sakač and
  • János J. Csanádi

Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174

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  • ]. The main approach in the synthesis of the tetrazoles is 1,3-dipolar cycloaddition between azide and nitrile. These reactions often follow the principles of “click” chemistry [20]. Although the formation of tetrazole in the Schmidt reaction of ketones was noted in the original study by Schmidt himself
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Published 20 Oct 2021

α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

  • Scott Benz and
  • Andrew S. Murkin

Beilstein J. Org. Chem. 2021, 17, 2570–2584, doi:10.3762/bjoc.17.172

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  • ring strain from cyclobutane derivatives has been developed by Cheng et al. to prepare functionalized α-amino cyclopentanones [31]. In the presence of a palladium catalyst, an electron-rich heteroarene 115 first adds to the nitrile group in a 1-cyanocyclobutyl ester 116 to give a tetrahedral imine
  • original source). Tandem synthesis of functionalized α-amino cyclopentanones 119 from heteroarenes 115 and cyclobutanone-derived cyanohydrins 116. a) Pd-catalyzed C–H addition of 115 to the nitrile group of 116 produces intermediates 117 and 118. An α-iminol rearrangement with ring expansion subsequently
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Published 15 Oct 2021

Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives

  • Yi Liu,
  • Puying Luo,
  • Yang Fu,
  • Tianxin Hao,
  • Xuan Liu,
  • Qiuping Ding and
  • Yiyuan Peng

Beilstein J. Org. Chem. 2021, 17, 2462–2476, doi:10.3762/bjoc.17.163

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  • ]. Then, they also reported another CuH-catalyzed coupling reaction of 1,3-enynes 54 and nitrile to prepare polysubstituted pyrroles 55 (Scheme 21) [66]. The substrates 54 could be easily prepared by Sonogashira coupling of terminal alkynes and vinyl halides. It is worth mentioning that the addition of
  • performed well in the reaction with 1,3-enynes 54, providing moderate yield and regioselectivity. The CuH-catalyzed intramolecular coupling of enyne containing a nitrile group worked smoothly and gave a moderate yield under standard conditions at a decreased concentration. A plausible mechanism according to
  • previously reported methods is proposed in Scheme 22. Firstly, the hydrocupration of enyne 54 with LCuH 57 provides propargylcopper intermediate 58. The 1,3-isomerization of 58 and the following nitrile addition produces imine intermediate 60, which subsequently undergoes intramolecular cyclization, a 1,5
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Published 22 Sep 2021
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