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    Azepine & Purine

    Uploaded by

    Aravindh

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd

    Azepine & Purine

    Uploaded by

    Aravindh
    21 views20 pages

    Original Title

    Azepine & Purine - PPT

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    © © All Rights Reserved

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    PPT, PDF, TXT or read online from Scribd

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    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    21 views20 pages

    Azepine & Purine

    Uploaded by

    Aravindh

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 20

    Unit-IV : CONTENT

    • Properties, synthesis, reactions & medicinal uses of…


    AZEPINES

    Properties
    1. Aromaticity
    AZEPINES

    Propertie
    2.Tautomerism

    1 /-/-azepine 3/-/-azepine 4/-/-azepine 2H-azepine

    Stability order : 3H > AH > IH


    AZEPINES

    Synthesis
    1. Valence-bond Isomerization
    AZEPINES

    Synthesis
    2. From Phenylazide
    AZEPINES

    Synthesis
    3. From Nitrobenzene

    - Deoxygenation of nitro group by tributyl-phosphine

    - Nucleophilic addition of Alkoxy group to arylnitrine


    - Rearrangement 2-alkoxy-3H-azepine
    AZEPINES
    Reactions
    1. Thermal reaction

    HN
    COOC2H5
    /\/-phenylcarbamate

    2. Ring contraction
    - Orbital symmetry controlled disrotatory electrocyclic process.
    AZEPINES
    Reactions
    3. Diels-Alder reaction -
    6+2 n electron reaction
    AZEPINES
    Medicinal Uses
    PURINE
    Properties
    1. Aromatic

    2,3-Benzopyrrole
    l//-benzo[b] pyiTole

    Each atom is sp2 hybridized , planar


    the total nu of delocalized e- are 10 (8 of eight C, 2 from N) follow the
    Huckefs rule

    2. Very weak base


    PURINE

    Properties
    3. Tautomerism
    7 H- and 9 H- tautomers are more stable

    1//-purine 9//-p urine 7//-purine

    7//-purine
    PURINE
    Synthesis
    1. Traube Synthesis
    PURINE

    Synthesis
    1. Traube Synthesis
    E.g.
    PURINE

    Synthesis
    2. From formamide
    Laboratory synthesis . formamide is heated in an vessel at 120 °C

    2018
    211
    PURINE

    Synthesis
    3. From substituted imidazole
    o
    OEt
    NaOEt r
    EtO +
    H2N
    diethyl
    carbonate 5-aminomidazole-4-carboxamide Xanthine

    2018
    212
    PURINE
    Reactions
    1. Electrophilic addition to N
    H

    H
    9H-purine 1-oxide
    2018
    213
    PURINE
    Reactions
    2. Electrophilic aromatic substitution
    0 O

    HNO3
    AcOH *
    A
    Xanthine Reaction is possible at 8th position.
    Oxy and amino derivatives react readily
    than non-substituted purines
    Br2
    AcOH *
    A
    Cl

    Azo compound
    2018
    PURINE
    Reactions
    3. Nucleophilic substitution
    - Nucleophilic displacement , where halides are the most popular leaving
    group

    EtO'Na
    OEt
    EtOH

    8-chloro-9-methyl-9/-/-punne 8-ethoxy-9-methyl-9H-purine

    2018
    215
    PURINE

    Medicinal uses
    (5) Nucleoside Antimetabolites: Acyclovir,: Valacvclovii; Ganciclovir,
    : TIdarabine
    - Antiviral asent

    athioprine
    (6) Antimetabolites : 6-Mercaptopurme, thioguanine, a:
    - Anticancer agent

    2018
    216
    PURINE

    Medicinal uses
    (5) Methylxanthines : Caffeine, theobromine
    - Drugs used in bronchial Asthma
    - Used as CNS stimulants

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