A de novo synthetic method to the access of N-substituted benzazepines

Ouchakour, Lamiaa; Nonn, Melinda; D’hooghe, Matthias; Kiss, Lóránd

doi:10.1016/j.jfluchem.2020.109466

Cited by 7 publications

(19 citation statements)

References 33 publications

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“…We also obtained benzo[ c ]azepanes from 1,2‐dihydronaphthalene using the new pathway (Scheme 7). Compounds 34 and 35 were prepared in somewhat lower yields than utilizing the dihydroxylation/C−C cleavage/reductive amination method, while the synthesis of compound 36 was significantly improved [7g] …”

Section: Resultsmentioning

confidence: 99%

An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles

et al. 2021

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An improved, efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization of various readily available cyclic compounds containing ring C=C bond. The stereocontrolled synthetic concept was based on the oxidative ring cleavage of various unsaturated scaffolds across ozonolysis followed by ring closing with double reductive amination with primary alkylamines or fluorinated alkylamines. The protocol provided versatile azaheterocyclic derivatives with a piperidine or azepane framework.

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Section: Resultsmentioning

confidence: 99%

An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles

et al. 2021

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“…The application of the ring-opening/ring-closing protocol has received importance for the synthesis of -amino acid derivatives as well. 72,74,75 Thus, the development of synthetic routes towards these compounds is of high practical importance, yet remains methodologically challenging. 76 In particular, -amino acids 73 are strongly related to -lactams, an important class of antibiotics.…”

Section: G Account Synlettmentioning

confidence: 99%

“…The process was stereocontrolled, that is, the stereochemistry of the starting compound (cis or trans) was retained in the product azepane amino esters. 74,75 Diols (±)-97, (±)-99, and (±)-101 were obtained by dihydroxylation of benzyl esters (±)-29 and (±)-30 (Scheme 19). 75 Some N-bridged bicyclic -amino acids were prepared from norbornene -amino ester (±)-33.…”

Section: Account Synlettmentioning

confidence: 99%

“…Vicinal diol (±)-143 submitted to oxidative ring cleavage gave dialdehyde T15, which then underwent reductive amination with 2,2,2-trifluoroethylamine and 2,2difluoroethylamine to provide trifluorinated and difluori-nated tetrahydroisoquinoline derivatives 144 and 145 (Scheme 29). 74 The protocol was further extended to the transformation of 2-methyl-1H-indene (146). After dihydroxylation with NMO/OsO 4 , oxidative ring cleavage followed by reductive ring closing with trifluoroethylamine led to isoquinoline derivative (±)-148 (Scheme 30).…”

Section: Account Synlettmentioning

confidence: 99%

“…The structure of several representatives of this group of bioactive products is shown in Figure 4. 96,97,99…”

Section: Figure 4 Representative Bioactive Substances Containing Benzazepine Moietymentioning

confidence: 99%

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Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

Kiss

Ouchakour

Nonn

et al. 2021

Synlett

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The current Account gives an insight into the synthesis of some N-heterocyclic β-amino acid derivatives and various functionalized saturated azaheterocycles accessed from substituted cycloalkenes via ring C=C bond oxidative cleavage followed by ring closing across double reductive amination. The ring-cleavage protocol has been accomplished according to two common approaches: a) Os-catalyzed dihydroxylation/NaIO4 vicinal diol oxidation and b) ozonolysis. A comparative study on these methodologies has been investigated. Due to the everincreasing relevance of organofluorine chemistry in drug research as well as of the high biological potential of β-amino acid derivatives several illustrative examples to the access of various fluorine-containing piperidine or azepane β-amino acid derivatives are also presented in the current Account.1 Introduction2 Olefin-Bond Transformation by Oxidative Ring Cleavage3 Synthesis of Saturated Azaheterocycles via Oxidative Ring-Opening/Ring-Closing Double Reductive Amination3.1 Importance of Fluorine-Containing Azaheterocycles in Pharmaceutical Research3.2 Synthesis of Azaheterocyclic Amino Acid Derivatives with a Piperidine or Azepane Framework through Oxidative Ring Opening/Reductive Amination3.2.1 Synthesis of Piperidine β-Amino Esters3.2.2 Synthesis of Azepane β-Amino Esters3.2.3 Synthesis of Fluorine-Containing Piperidine γ-Amino Esters3.3 Synthesis of Tetrahydroisoquinoline Derivatives through Oxidative Ring Opening/Reductive Amination Protocol3.4 Synthesis of Functionalized Benzazepines through Reductive Amination3.4.1 Synthesis of Benzo[c]azepines3.4.2 Synthesis of Benzo[d]azepines3.5 Synthesis of Various N-Heterocycles via Ozonolysis/Reductive Amination3.5.1 Synthesis of Compounds with an Azepane Ring3.5.2 Synthesis of Piperidine β-Amino Acids and Piperidine-Fused β-Lactams3.5.3 Synthesis of γ-Lactams with a Piperidine Ring3.5.4 Synthesis of other N-Heterocycles4 Summary and Outlook5 List of Abbreviations

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Application of Metathesis Protocols to the Stereocontrolled Synthesis of some Functionalized β‐Amino Esters and Azaheterocycles

Semghouli,

Nonn,

Remete

et al. 2023

The Chemical Record

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In this account our aim was to give an insight into the application of metathesis protocols (ROM, RCM, RCEYM, CM, RRM) for the synthesis of various azaheterocyclic frameworks. Due to the high biological potential and importance in peptide chemistry and drug design of β‐amino acids our intention is to give a highlight on the synthetic procedures and transformation of these class of compounds with the above‐mentioned metathesis strategies with emphasis on selectivity, stereocontrol, substrate‐directing effect or functional group tolerance.

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A de novo synthetic method to the access of N-substituted benzazepines

Cited by 7 publications

References 33 publications

An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles

An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles

Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

Application of Metathesis Protocols to the Stereocontrolled Synthesis of some Functionalized β‐Amino Esters and Azaheterocycles

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