Transformations of 1-phenethyl-1,2,3,6-tetrahydropyridines in the presence of trifluoromethanesulfonic acid View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2020-07

AUTHORS

Vera A. Shadrikova, Alexander S. Popov, Maria V. Termelyova, Marat R. Baimuratov, Yuri N. Klimochkin

ABSTRACT

1-Phenethyl-1,2,3,6-tetrahydropyridines undergo intramolecular Friedel–Crafts reaction in trifluoromethanesulfonic acid medium, resulting in the formation of azatricyclic structures. It was shown that the direction of this reaction depended on the position of the substituent relative to the multiple bond in tetrahydropyridine. The structures of the obtained compounds were confirmed by a set of spectral analysis methods. More... »

PAGES

909-914

References to SciGraph publications

  • 2015-10. Synthesis of adamantyl-containing phenylpiperidines in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2017-11. The Ritter reaction for the synthesis of heterocycles in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2010-05. Effect of structure of nucleophile and substrate on the quaternization of heterocyclic amines in RUSSIAN JOURNAL OF GENERAL CHEMISTRY
  • 2016-10. Synthesis of substituted 1-[2-(adamantan-1-yl)ethyl]piperidines in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2003-07. Transformation of 1,2,5,6-Tetrahydropyridines with Mycellar Fungi in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2010-08-12. Synthesis and special features of the structure of 6(7)-aminoperimidine derivatives in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 1991-03. Superacid cyclization of homo- and bishomoisoprenoid acids in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/s10593-020-02748-8

    DOI

    http://dx.doi.org/10.1007/s10593-020-02748-8

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1130273517


    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": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Shadrikova", 
            "givenName": "Vera A.", 
            "id": "sg:person.015226001707.75", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015226001707.75"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Popov", 
            "givenName": "Alexander S.", 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Termelyova", 
            "givenName": "Maria V.", 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Baimuratov", 
            "givenName": "Marat R.", 
            "id": "sg:person.011031671452.57", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011031671452.57"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia", 
              "id": "http://www.grid.ac/institutes/grid.445792.9", 
              "name": [
                "Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Klimochkin", 
            "givenName": "Yuri N.", 
            "id": "sg:person.07436126201.08", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07436126201.08"
            ], 
            "type": "Person"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1023/a:1026142220384", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1024138072", 
              "https://doi.org/10.1023/a:1026142220384"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s10593-018-2189-y", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1100198891", 
              "https://doi.org/10.1007/s10593-018-2189-y"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf00474221", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1028780719", 
              "https://doi.org/10.1007/bf00474221"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s10593-015-1792-4", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1024652134", 
              "https://doi.org/10.1007/s10593-015-1792-4"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1134/s1070428016100146", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1062738321", 
              "https://doi.org/10.1134/s1070428016100146"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/s10593-010-0532-z", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1041825246", 
              "https://doi.org/10.1007/s10593-010-0532-z"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1134/s1070363210050294", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1007807471", 
              "https://doi.org/10.1134/s1070363210050294"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "2020-07", 
        "datePublishedReg": "2020-07-01", 
        "description": "1-Phenethyl-1,2,3,6-tetrahydropyridines undergo intramolecular Friedel\u2013Crafts reaction in trifluoromethanesulfonic acid medium, resulting in the formation of azatricyclic structures. It was shown that the direction of this reaction depended on the position of the substituent relative to the multiple bond in tetrahydropyridine. The structures of the obtained compounds were confirmed by a set of spectral analysis methods.", 
        "genre": "article", 
        "id": "sg:pub.10.1007/s10593-020-02748-8", 
        "inLanguage": "en", 
        "isAccessibleForFree": false, 
        "isFundedItemOf": [
          {
            "id": "sg:grant.9417841", 
            "type": "MonetaryGrant"
          }
        ], 
        "isPartOf": [
          {
            "id": "sg:journal.1358699", 
            "issn": [
              "0132-6244", 
              "1573-8353"
            ], 
            "name": "Chemistry of Heterocyclic Compounds", 
            "publisher": "Springer Nature", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "7", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "56"
          }
        ], 
        "keywords": [
          "intramolecular Friedel-Crafts reaction", 
          "Friedel-Crafts reaction", 
          "multiple bonds", 
          "acid medium", 
          "trifluoromethanesulfonic acid", 
          "reaction", 
          "substituents", 
          "bonds", 
          "structure", 
          "compounds", 
          "acid", 
          "formation", 
          "tetrahydropyridine", 
          "presence", 
          "medium", 
          "transformation", 
          "method", 
          "analysis method", 
          "position", 
          "spectral analysis method", 
          "direction", 
          "set", 
          "trifluoromethanesulfonic acid medium", 
          "azatricyclic structures"
        ], 
        "name": "Transformations of 1-phenethyl-1,2,3,6-tetrahydropyridines in the presence of trifluoromethanesulfonic acid", 
        "pagination": "909-914", 
        "productId": [
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1130273517"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1007/s10593-020-02748-8"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1007/s10593-020-02748-8", 
          "https://app.dimensions.ai/details/publication/pub.1130273517"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2022-01-01T18:57", 
        "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_845.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "https://doi.org/10.1007/s10593-020-02748-8"
      }
    ]
     

    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.10.1007/s10593-020-02748-8'

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

    curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s10593-020-02748-8'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s10593-020-02748-8'

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

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s10593-020-02748-8'


     

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

    138 TRIPLES      22 PREDICATES      57 URIs      42 LITERALS      6 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1007/s10593-020-02748-8 schema:about anzsrc-for:03
    2 anzsrc-for:0305
    3 schema:author N05e779fd488344bd9db64631acb45cb1
    4 schema:citation sg:pub.10.1007/bf00474221
    5 sg:pub.10.1007/s10593-010-0532-z
    6 sg:pub.10.1007/s10593-015-1792-4
    7 sg:pub.10.1007/s10593-018-2189-y
    8 sg:pub.10.1023/a:1026142220384
    9 sg:pub.10.1134/s1070363210050294
    10 sg:pub.10.1134/s1070428016100146
    11 schema:datePublished 2020-07
    12 schema:datePublishedReg 2020-07-01
    13 schema:description 1-Phenethyl-1,2,3,6-tetrahydropyridines undergo intramolecular Friedel–Crafts reaction in trifluoromethanesulfonic acid medium, resulting in the formation of azatricyclic structures. It was shown that the direction of this reaction depended on the position of the substituent relative to the multiple bond in tetrahydropyridine. The structures of the obtained compounds were confirmed by a set of spectral analysis methods.
    14 schema:genre article
    15 schema:inLanguage en
    16 schema:isAccessibleForFree false
    17 schema:isPartOf N0f80cb3022ce419a9f4a023ae9bba0dc
    18 N59a175b8d6164cd0aa3167225ae20679
    19 sg:journal.1358699
    20 schema:keywords Friedel-Crafts reaction
    21 acid
    22 acid medium
    23 analysis method
    24 azatricyclic structures
    25 bonds
    26 compounds
    27 direction
    28 formation
    29 intramolecular Friedel-Crafts reaction
    30 medium
    31 method
    32 multiple bonds
    33 position
    34 presence
    35 reaction
    36 set
    37 spectral analysis method
    38 structure
    39 substituents
    40 tetrahydropyridine
    41 transformation
    42 trifluoromethanesulfonic acid
    43 trifluoromethanesulfonic acid medium
    44 schema:name Transformations of 1-phenethyl-1,2,3,6-tetrahydropyridines in the presence of trifluoromethanesulfonic acid
    45 schema:pagination 909-914
    46 schema:productId N5445542691ac47cdac41436aa0daa50a
    47 Nc7827f0cbfb04bcba871ffcb38c09c81
    48 schema:sameAs https://app.dimensions.ai/details/publication/pub.1130273517
    49 https://doi.org/10.1007/s10593-020-02748-8
    50 schema:sdDatePublished 2022-01-01T18:57
    51 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    52 schema:sdPublisher N08836df5a165469b8f174dd03d3c8e28
    53 schema:url https://doi.org/10.1007/s10593-020-02748-8
    54 sgo:license sg:explorer/license/
    55 sgo:sdDataset articles
    56 rdf:type schema:ScholarlyArticle
    57 N05e779fd488344bd9db64631acb45cb1 rdf:first sg:person.015226001707.75
    58 rdf:rest N797abb0c0d614008b9c0c5b3f64e50a2
    59 N08836df5a165469b8f174dd03d3c8e28 schema:name Springer Nature - SN SciGraph project
    60 rdf:type schema:Organization
    61 N0f80cb3022ce419a9f4a023ae9bba0dc schema:issueNumber 7
    62 rdf:type schema:PublicationIssue
    63 N2d4ba7be14734458bafa5c522668d040 rdf:first sg:person.011031671452.57
    64 rdf:rest Ncc119827186f4d9f94925d71f0e38af4
    65 N5445542691ac47cdac41436aa0daa50a schema:name dimensions_id
    66 schema:value pub.1130273517
    67 rdf:type schema:PropertyValue
    68 N59a175b8d6164cd0aa3167225ae20679 schema:volumeNumber 56
    69 rdf:type schema:PublicationVolume
    70 N797abb0c0d614008b9c0c5b3f64e50a2 rdf:first Ndcc8c03cebeb4d4faaae9684855b2b37
    71 rdf:rest N912e758dac5f42bca38b24f955ca565a
    72 N912e758dac5f42bca38b24f955ca565a rdf:first N920541a6f6b74442a420122c40cebe32
    73 rdf:rest N2d4ba7be14734458bafa5c522668d040
    74 N920541a6f6b74442a420122c40cebe32 schema:affiliation grid-institutes:grid.445792.9
    75 schema:familyName Termelyova
    76 schema:givenName Maria V.
    77 rdf:type schema:Person
    78 Nc7827f0cbfb04bcba871ffcb38c09c81 schema:name doi
    79 schema:value 10.1007/s10593-020-02748-8
    80 rdf:type schema:PropertyValue
    81 Ncc119827186f4d9f94925d71f0e38af4 rdf:first sg:person.07436126201.08
    82 rdf:rest rdf:nil
    83 Ndcc8c03cebeb4d4faaae9684855b2b37 schema:affiliation grid-institutes:grid.445792.9
    84 schema:familyName Popov
    85 schema:givenName Alexander S.
    86 rdf:type schema:Person
    87 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
    88 schema:name Chemical Sciences
    89 rdf:type schema:DefinedTerm
    90 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
    91 schema:name Organic Chemistry
    92 rdf:type schema:DefinedTerm
    93 sg:grant.9417841 http://pending.schema.org/fundedItem sg:pub.10.1007/s10593-020-02748-8
    94 rdf:type schema:MonetaryGrant
    95 sg:journal.1358699 schema:issn 0132-6244
    96 1573-8353
    97 schema:name Chemistry of Heterocyclic Compounds
    98 schema:publisher Springer Nature
    99 rdf:type schema:Periodical
    100 sg:person.011031671452.57 schema:affiliation grid-institutes:grid.445792.9
    101 schema:familyName Baimuratov
    102 schema:givenName Marat R.
    103 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011031671452.57
    104 rdf:type schema:Person
    105 sg:person.015226001707.75 schema:affiliation grid-institutes:grid.445792.9
    106 schema:familyName Shadrikova
    107 schema:givenName Vera A.
    108 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015226001707.75
    109 rdf:type schema:Person
    110 sg:person.07436126201.08 schema:affiliation grid-institutes:grid.445792.9
    111 schema:familyName Klimochkin
    112 schema:givenName Yuri N.
    113 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07436126201.08
    114 rdf:type schema:Person
    115 sg:pub.10.1007/bf00474221 schema:sameAs https://app.dimensions.ai/details/publication/pub.1028780719
    116 https://doi.org/10.1007/bf00474221
    117 rdf:type schema:CreativeWork
    118 sg:pub.10.1007/s10593-010-0532-z schema:sameAs https://app.dimensions.ai/details/publication/pub.1041825246
    119 https://doi.org/10.1007/s10593-010-0532-z
    120 rdf:type schema:CreativeWork
    121 sg:pub.10.1007/s10593-015-1792-4 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024652134
    122 https://doi.org/10.1007/s10593-015-1792-4
    123 rdf:type schema:CreativeWork
    124 sg:pub.10.1007/s10593-018-2189-y schema:sameAs https://app.dimensions.ai/details/publication/pub.1100198891
    125 https://doi.org/10.1007/s10593-018-2189-y
    126 rdf:type schema:CreativeWork
    127 sg:pub.10.1023/a:1026142220384 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024138072
    128 https://doi.org/10.1023/a:1026142220384
    129 rdf:type schema:CreativeWork
    130 sg:pub.10.1134/s1070363210050294 schema:sameAs https://app.dimensions.ai/details/publication/pub.1007807471
    131 https://doi.org/10.1134/s1070363210050294
    132 rdf:type schema:CreativeWork
    133 sg:pub.10.1134/s1070428016100146 schema:sameAs https://app.dimensions.ai/details/publication/pub.1062738321
    134 https://doi.org/10.1134/s1070428016100146
    135 rdf:type schema:CreativeWork
    136 grid-institutes:grid.445792.9 schema:alternateName Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia
    137 schema:name Samara State Technical University, 244 Molodogvardeiskaya St., 443100, Samara, Russia
    138 rdf:type schema:Organization
     




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


    ...