Synthetic exploitation of halogenated alkenes containing EWG: benzotriazole-mediated synthesis of benzoazetines and thermal transformations

Tuyun, Amaç Fatih

doi:10.1039/c4ra01425a

Cited by 4 publications

(1 citation statement)

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“…To the best of our knowledge, in addition to the TBAF-assisted process mentioned above, only one example of anti-Michael 5- endo-dig hydroamination of an alkynoate ester has been reported; and in that case, the cyclization was favored by the particular structure of the substrate, possessing a crowded quaternary center ( gem -dimethyl effect). Alternatively, Michael-type cyclization of 3 , affording a strained benzazetine ring, could also be possible, at least in principle: one example of 4- exo-dig Pd-catalyzed intramolecular hydroamination of gem-difluoropropargylamides has been described, and the formation of the β-lactam ring was driven by the polarization of the triple bond induced by fluorine substituents. Moreover, we have recently reported that, in the presence of cationic Au(I) complex (JonPhosAuNCMe)SbF 6 , substrates 3 underwent a sequential reaction, affording eight-membered dibenzo[1,5]diazocines 5 (Scheme a) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

et al. 2018

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β-(2-Aminophenyl)-α,β-ynones afforded 3-unsubstituted 2-acylindoles in good yields in the presence of 20 mol % AgOTf under (microwave) MW heating. The use CuOTf as a catalyst resulted in a similar reaction outcome, generally with a lower efficiency. This transformation represents the first example of 5- endo-dig cyclization of 2-alkynylanilines bearing an acyl group linked to the triple bond. By contrast with the previously reported gold-catalyzed reaction of β-(2-aminophenyl)-α,β-ynones, which resulted in the formation of dibenzo[1,5]diazocines through a sequential process triggered by an intermolecular hydroamination, a selective intramolecular anti-Michael hydroamination was observed in the present study by silver/copper catalysis. Density functional theory calculations on the Ag-catalyzed reaction revealed that the catalyst induces an electrostatic arrangement in the TS coherent with the experimentally observed cyclization.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

et al. 2018

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Synthesis of 2,3‐Fused Indoline Aminals via 4 + 2 Cycloaddition of NH‐free Benzazetidines with Indoles

et al. 2018

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Summary of main observation and conclusion A 4 + 2 cycloaddition reaction of NH‐free benzazetidines with indoles under the catalysis of camphorsulfonic acid was developed. This method shows a broad substrate scope of benzazetidines and indoles, and offers a convenient method for stereoselective synthesis of various cis‐2,3‐fused indoline aminals. Preliminary mechanistic studies suggest the reaction proceed via a stepwise pathway featuring an electrophilic attack on the benzylic carbon of benzazetidine.

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Four-Membered Ring Systems

Alcaide¹,

Almendros²

2015

Progress in Heterocyclic Chemistry

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Synthetic exploitation of halogenated alkenes containing EWG: benzotriazole-mediated synthesis of benzoazetines and thermal transformations

Abstract: The stable benzoazetines (5a–d) based on nitrovinyl moieties have been synthesizedviatransamination of bisbenzotriazolyl derivatives (2a–c).

Cited by 4 publications

References 40 publications

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

Synthesis of 2,3‐Fused Indoline Aminals via 4 + 2 Cycloaddition of NH‐free Benzazetidines with Indoles

Four-Membered Ring Systems

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