Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils

Arcadi, Antonio; Chiarini, Marco; Vecchio, Luana Del; Marinelli, Fabio; Michelet, Véronique

doi:10.1002/ejoc.201601600

Cited by 19 publications

(5 citation statements)

References 95 publications

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“…The authors also observedt he same silver-catalyzed intramolecular hydroamination reactioni nafollow-up paper;t his time indole 71 was isolated in a3 7% yield when aniline 10 was heated in the presence of AgNO 3 and al arge excess of H 2 O 2 in am ethanol/water solvent system (Scheme 22). [25] Again, the oxidant appears not to be involved in this reaction.…”

Section: Hydroamination Strategiesmentioning

confidence: 92%

Indole Synthesis Using Silver Catalysis

Clarke

Rossi‐Ashton

et al. 2019

Chemistry An Asian Journal

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Indoles are amongst the most important classes of heteroaromatics in organic chemistry,c ommonly found in biologicallya ctive naturalp roductsa nd therapeutically useful compounds. The synthesis of indoles is therefore important and severalm ethods for their synthesis that make use of silver(I)c atalysts and reagents have been developed in recent years. This Minireview contains, to the best of our knowledge,acomprehensive coverageo fs ilver-mediated indole forming reactions since the first reactiono ft his type was reported in 2004.Scheme1.Generalsilver(I)-catalyzed hydroaminations equence.[a] Dr.Scheme4.Ag I -catalyzed hydroamination to prepare indole 14.Scheme5.Ag I -catalyzed hydroamination to prepare indoles 18.Scheme6.Ag I -catalyzed hydroamination to prepare 3-vinyli ndoles 21. Scheme 7. Proposed mechanism for the synthesis of indole 21.

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Section: Hydroamination Strategiesmentioning

confidence: 92%

Indole Synthesis Using Silver Catalysis

Clarke

Rossi‐Ashton

et al. 2019

Chemistry An Asian Journal

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“…Benzisoxazoles 91 were produced from o ‐alkynylanilines 90 under silver catalysis and oxone as a terminal oxidant in acetonitrile‐water solvent system (Scheme 30). Such reactions were restricted to the use of N ‐unsubstituted anilines only [115] …”

Section: Synthesis Of Indolines Oxindoles Indoxylesmentioning

confidence: 99%

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

2022

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The transformations of 2‐alkynylanilines and their derivatives into heterocycles are surveyed. Depending on the substituents, catalysts, and reaction conditions, these substrates can be converted into indoles, quinolines, indolines, oxindoles, indoxiles, various polycyclic compounds, etc. This review aims to generalize and assess the patterns of reactivity, selectivity, and applicability of 2‐(alkynyl)anilines in heterocyclic chemistry. The review is divided into sections in accordance with the produced heterocycle. In summary, the title substrates are capable of cyclizing not only into five‐ and six‐membered rings, but also to produce seven‐ and even eight‐membered ring systems. The preparation of 2‐(alkynyl)anilines is not covered.

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“…1 H NMR (400 MHz, CDCl 3 ):  = 7.36 -7.21 (m, 5 H, 12, 13, 14, 15, 16), 6.14 (d, J = 5.7 Hz, 1 H, 4a), 6.10 (d, J = 5.7 Hz, 1 H, 4b), 5.10 (d, J = 5.7 Hz, 1 H, 5a), 5.06 (d, J = 5.7 Hz, 1 H, 5b), 3.95 (d, J = 10.5 Hz, 1 H, 2b′), 3.81 (dd, J = 10.5, 1.2 Hz, 1 H, 2a′), 3.64 (d, J = 10.5 Hz, 1 H, 2a′′), 3.51 (dd, J = 10.5, 1.2 Hz, 1 H, 2b′′), 2.83 (q, J = 7.3 Hz, 1 H, 9b), 2.77 (q, J = 7.3 Hz, 1 H, 9a), 1.48 (d,J = 7.3 Hz,3 H,10b),1.46 (d,J = 7.3 Hz,3 H,10b),1.39 (s,3 H,8a),1.36 (s,3 H,8b), 1.21 (d, J = 4.0 Hz, 1 H, 7b′), 1.08 (d, J = 4.2 Hz, 1 H, 7a′), 0.82 (dd, J = 4.3, 1.2 Hz, 1 H, 7a′′), 0.58 (dd, J = 4.0, 1.2 Hz, 1 H, 7b′′). 13 C NMR (101 MHz, CDCl 3 ):  = 143.73 (C,11a),143.04 (C,11b),141.33 (CH,4a),141.04 (CH,4b),128.25 (2 × CH,13a,15a),128.24 (2 × CH,13b,15b),127.74 (2 × CH,12b,16b),127.43 (2 × CH,12a,16a),126.30 (CH,14b),126.04 (CH,14a),112.93 (CH,5a),112.64 (CH,5b) 3-Oxabicyclo[4.1.0]hept-4-ene 2o was obtained following general procedure 3 from 1o (1 mmol, 200 mg), IPrAuCl (2 mol%, 13 mg), and NaBAr F (2 mol%, 18 mg) in 4 h followed by purification by flash chromatography (silica gel; pentane/Et 2 O, 99:1).…”

Section: -Methyl-1-(1-phenylethyl)-3-oxabicyclo[410]hept-4-ene (2n)mentioning

confidence: 99%

Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry

et al. 2021

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The synthesis of original structures for the fragrance industry bearing bicyclic scaffolds is described. To the best of our knowledge, these structures are not found in the fragrance industry neither from natural nor synthetic pathways. NHC gold type catalysts showed excellent activities leading to light bicyclic enol ethers. Several bicyclic adducts were prepared in good to excellent yields (18-99%). Evaluation of NHC-Au complexes allowed to reach a TOF of 300 h-1. The evaluation for the organoleptic properties of [4.1.0]-bicyclic ethers were compared with the unprecedented properties of the 1,6-enyne precursors. The evaluations of starting materials showed a great interest on these structures with various olfactive facets. In this study we depicted the similarity and differences between starting ethers and their cycloisomerized bicyclic counterparts.

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Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils

Cited by 19 publications

References 95 publications

Indole Synthesis Using Silver Catalysis

Indole Synthesis Using Silver Catalysis

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

Oxygen-Tethered 1,6-Enynes and [4.1.0]-Bicyclic Ether Skeletons as Hedonic Materials for the Fragrance Industry

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