Synthesis of 1-{4a,6-dimethyl-4a,9a-dihydropyrano-[3,4-b]indol-9(1H)-yl}ethanone View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2012-03

AUTHORS

D. A. Skladchikov, A. A. Fatykhov, R. R. Gataullin

ABSTRACT

Heating of the bromination product of 4-methyl-3,6-dihydro-2H-pyran with 4-toluidine or 2-bromo-4-methylamiline in triethylamine gave 4-methyl-N-(4-methylphenyl)- and N-(2-bromo-4-methylphenyl)-4-methyl-3,6-dihydro-2H-pyran-3-amines which were converted into the corresponding amides by reaction with bromo- or chloroacetyl chloride. 1-{4a,6-Dimethyl-4a,9a-dihydropyrano[3,4-b]indol-9(1H)-yl} ethanone was synthesized in good yield by heating N-(2-bromo-4-methylphenyl)-N-(4-methyl-3,6-dihydro-2Hpyran-3-yl)acetamide in boiling toluene in the presence of palladium(II) acetate, triphenylphosphine, copper(II) acetate, triethylamine, and potassium carbonate. More... »

PAGES

383-386

References to SciGraph publications

  • 2010-07. Palladium-catalyzed amination in the synthesis of polyazamacrocycles in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1134/s1070428012030086

    DOI

    http://dx.doi.org/10.1134/s1070428012030086

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1045015566


    Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
    Incoming Citations Browse incoming citations for this publication using opencitations.net

    JSON-LD is the canonical representation for SciGraph data.

    TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

    [
      {
        "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
        "about": [
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Chemical Sciences", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Organic Chemistry", 
            "type": "DefinedTerm"
          }
        ], 
        "author": [
          {
            "affiliation": {
              "alternateName": "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia", 
              "id": "http://www.grid.ac/institutes/grid.4886.2", 
              "name": [
                "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Skladchikov", 
            "givenName": "D. A.", 
            "id": "sg:person.07632042773.00", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07632042773.00"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia", 
              "id": "http://www.grid.ac/institutes/grid.4886.2", 
              "name": [
                "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Fatykhov", 
            "givenName": "A. A.", 
            "id": "sg:person.016071311024.10", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016071311024.10"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia", 
              "id": "http://www.grid.ac/institutes/grid.4886.2", 
              "name": [
                "Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Gataullin", 
            "givenName": "R. R.", 
            "id": "sg:person.015514576570.48", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015514576570.48"
            ], 
            "type": "Person"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1134/s1070428010070018", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1045549300", 
              "https://doi.org/10.1134/s1070428010070018"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "2012-03", 
        "datePublishedReg": "2012-03-01", 
        "description": "Heating of the bromination product of 4-methyl-3,6-dihydro-2H-pyran with 4-toluidine or 2-bromo-4-methylamiline in triethylamine gave 4-methyl-N-(4-methylphenyl)- and N-(2-bromo-4-methylphenyl)-4-methyl-3,6-dihydro-2H-pyran-3-amines which were converted into the corresponding amides by reaction with bromo- or chloroacetyl chloride. 1-{4a,6-Dimethyl-4a,9a-dihydropyrano[3,4-b]indol-9(1H)-yl} ethanone was synthesized in good yield by heating N-(2-bromo-4-methylphenyl)-N-(4-methyl-3,6-dihydro-2Hpyran-3-yl)acetamide in boiling toluene in the presence of palladium(II) acetate, triphenylphosphine, copper(II) acetate, triethylamine, and potassium carbonate.", 
        "genre": "article", 
        "id": "sg:pub.10.1134/s1070428012030086", 
        "inLanguage": "en", 
        "isAccessibleForFree": false, 
        "isPartOf": [
          {
            "id": "sg:journal.1136317", 
            "issn": [
              "0514-7492", 
              "1070-4280"
            ], 
            "name": "Russian Journal of Organic Chemistry", 
            "publisher": "Pleiades Publishing", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "3", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "48"
          }
        ], 
        "keywords": [
          "bromination products", 
          "chloroacetyl chloride", 
          "good yields", 
          "potassium carbonate", 
          "heating", 
          "products", 
          "pyran", 
          "triethylamine", 
          "corresponding amides", 
          "amides", 
          "reaction", 
          "bromo", 
          "chloride", 
          "ethanone", 
          "yield", 
          "toluene", 
          "presence", 
          "acetate", 
          "triphenylphosphine", 
          "carbonate", 
          "synthesis", 
          "pyran-3-amines"
        ], 
        "name": "Synthesis of 1-{4a,6-dimethyl-4a,9a-dihydropyrano-[3,4-b]indol-9(1H)-yl}ethanone", 
        "pagination": "383-386", 
        "productId": [
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1045015566"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1134/s1070428012030086"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1134/s1070428012030086", 
          "https://app.dimensions.ai/details/publication/pub.1045015566"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2022-01-01T18:28", 
        "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
        "sdPublisher": {
          "name": "Springer Nature - SN SciGraph project", 
          "type": "Organization"
        }, 
        "sdSource": "s3://com-springernature-scigraph/baseset/20220101/entities/gbq_results/article/article_568.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "https://doi.org/10.1134/s1070428012030086"
      }
    ]
     

    Download the RDF metadata as:  json-ld nt turtle xml License info

    HOW TO GET THIS DATA PROGRAMMATICALLY:

    JSON-LD is a popular format for linked data which is fully compatible with JSON.

    curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1134/s1070428012030086'

    N-Triples is a line-based linked data format ideal for batch operations.

    curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1134/s1070428012030086'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1134/s1070428012030086'

    RDF/XML is a standard XML format for linked data.

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1134/s1070428012030086'


     

    This table displays all metadata directly associated to this object as RDF triples.

    98 TRIPLES      22 PREDICATES      49 URIs      40 LITERALS      6 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1134/s1070428012030086 schema:about anzsrc-for:03
    2 anzsrc-for:0305
    3 schema:author Ndeace2b7833449e5a0c0e315f3fb90c5
    4 schema:citation sg:pub.10.1134/s1070428010070018
    5 schema:datePublished 2012-03
    6 schema:datePublishedReg 2012-03-01
    7 schema:description Heating of the bromination product of 4-methyl-3,6-dihydro-2H-pyran with 4-toluidine or 2-bromo-4-methylamiline in triethylamine gave 4-methyl-N-(4-methylphenyl)- and N-(2-bromo-4-methylphenyl)-4-methyl-3,6-dihydro-2H-pyran-3-amines which were converted into the corresponding amides by reaction with bromo- or chloroacetyl chloride. 1-{4a,6-Dimethyl-4a,9a-dihydropyrano[3,4-b]indol-9(1H)-yl} ethanone was synthesized in good yield by heating N-(2-bromo-4-methylphenyl)-N-(4-methyl-3,6-dihydro-2Hpyran-3-yl)acetamide in boiling toluene in the presence of palladium(II) acetate, triphenylphosphine, copper(II) acetate, triethylamine, and potassium carbonate.
    8 schema:genre article
    9 schema:inLanguage en
    10 schema:isAccessibleForFree false
    11 schema:isPartOf N101e2a8851c1449d8b46a3b3bcacae48
    12 Nc8be3dcaba224d029ff402dafe9f5669
    13 sg:journal.1136317
    14 schema:keywords acetate
    15 amides
    16 bromination products
    17 bromo
    18 carbonate
    19 chloride
    20 chloroacetyl chloride
    21 corresponding amides
    22 ethanone
    23 good yields
    24 heating
    25 potassium carbonate
    26 presence
    27 products
    28 pyran
    29 pyran-3-amines
    30 reaction
    31 synthesis
    32 toluene
    33 triethylamine
    34 triphenylphosphine
    35 yield
    36 schema:name Synthesis of 1-{4a,6-dimethyl-4a,9a-dihydropyrano-[3,4-b]indol-9(1H)-yl}ethanone
    37 schema:pagination 383-386
    38 schema:productId N045456f5bd1845a88b167110c7746eca
    39 Nbff03b9dcf5843edb5bba2890c896cc3
    40 schema:sameAs https://app.dimensions.ai/details/publication/pub.1045015566
    41 https://doi.org/10.1134/s1070428012030086
    42 schema:sdDatePublished 2022-01-01T18:28
    43 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    44 schema:sdPublisher Nd6fe2c34c8b44870adee2555b0deddf5
    45 schema:url https://doi.org/10.1134/s1070428012030086
    46 sgo:license sg:explorer/license/
    47 sgo:sdDataset articles
    48 rdf:type schema:ScholarlyArticle
    49 N045456f5bd1845a88b167110c7746eca schema:name doi
    50 schema:value 10.1134/s1070428012030086
    51 rdf:type schema:PropertyValue
    52 N08c4b3fa23a44a0eb07546a76f374b58 rdf:first sg:person.015514576570.48
    53 rdf:rest rdf:nil
    54 N101e2a8851c1449d8b46a3b3bcacae48 schema:issueNumber 3
    55 rdf:type schema:PublicationIssue
    56 N733dd460057c425b911e0a636c6be83d rdf:first sg:person.016071311024.10
    57 rdf:rest N08c4b3fa23a44a0eb07546a76f374b58
    58 Nbff03b9dcf5843edb5bba2890c896cc3 schema:name dimensions_id
    59 schema:value pub.1045015566
    60 rdf:type schema:PropertyValue
    61 Nc8be3dcaba224d029ff402dafe9f5669 schema:volumeNumber 48
    62 rdf:type schema:PublicationVolume
    63 Nd6fe2c34c8b44870adee2555b0deddf5 schema:name Springer Nature - SN SciGraph project
    64 rdf:type schema:Organization
    65 Ndeace2b7833449e5a0c0e315f3fb90c5 rdf:first sg:person.07632042773.00
    66 rdf:rest N733dd460057c425b911e0a636c6be83d
    67 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
    68 schema:name Chemical Sciences
    69 rdf:type schema:DefinedTerm
    70 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
    71 schema:name Organic Chemistry
    72 rdf:type schema:DefinedTerm
    73 sg:journal.1136317 schema:issn 0514-7492
    74 1070-4280
    75 schema:name Russian Journal of Organic Chemistry
    76 schema:publisher Pleiades Publishing
    77 rdf:type schema:Periodical
    78 sg:person.015514576570.48 schema:affiliation grid-institutes:grid.4886.2
    79 schema:familyName Gataullin
    80 schema:givenName R. R.
    81 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015514576570.48
    82 rdf:type schema:Person
    83 sg:person.016071311024.10 schema:affiliation grid-institutes:grid.4886.2
    84 schema:familyName Fatykhov
    85 schema:givenName A. A.
    86 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016071311024.10
    87 rdf:type schema:Person
    88 sg:person.07632042773.00 schema:affiliation grid-institutes:grid.4886.2
    89 schema:familyName Skladchikov
    90 schema:givenName D. A.
    91 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07632042773.00
    92 rdf:type schema:Person
    93 sg:pub.10.1134/s1070428010070018 schema:sameAs https://app.dimensions.ai/details/publication/pub.1045549300
    94 https://doi.org/10.1134/s1070428010070018
    95 rdf:type schema:CreativeWork
    96 grid-institutes:grid.4886.2 schema:alternateName Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia
    97 schema:name Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, 450054, Ufa, Bashkortostan, Russia
    98 rdf:type schema:Organization
     




    Preview window. Press ESC to close (or click here)


    ...