Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and ... View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2016-07

AUTHORS

I. Yu. Danilyuk, R. I. Vas’kevich, A. I. Vas’kevich, M. V. Vovk

ABSTRACT

Intramolecular cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides on heating in polyphosphoric acid afforded 8-aryl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones and 5-aryl-1-(thiophen-3-yl)pyrrolidin-2-ones. Cyclofunctionalization of the title compounds with (chlorosulfanyl)benzene and 4-(chlorosulfanyl)-toluene led to the formation of 8-aryl-7-arylsulfanyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones or their mixtures with 5-aryl-4-arylsulfanyltetrahydrofuran-2-ones. 1-(Chlorosulfanyl)-4-nitrobenzene reacted with 4-(4-methylphenyl)-N-(thiophen-3-yl)but-3-enamide and 4-(4-fluorophenyl)-N-(thiophen-3-yl)but-3-enamide to give 5-(4-methylphenyl)-4-(4-nitrophenylsulfanyl)-1-(thiophen-3-yl)pyrrolidin-2-one and 5-(4-fluorophenyl)-4-(4-nitrophenylsulfanyl)tetrahydrofuran-2-one, respectively.

PAGES

987-992

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428016070113

DOI

http://dx.doi.org/10.1134/s1070428016070113

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1035604519


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/2008/0305", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Organic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "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"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.464621.3", 
          "name": [
            "Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02094, Kiev, Ukraine"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Danilyuk", 
        "givenName": "I. Yu.", 
        "id": "sg:person.016325116525.94", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016325116525.94"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.464621.3", 
          "name": [
            "Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02094, Kiev, Ukraine", 
            "\u201cEnamine\u201d Scientific Production Association, ul. Chervonotkats\u2019ka 78, 02094, Kiev, Ukraine"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Vas\u2019kevich", 
        "givenName": "R. I.", 
        "id": "sg:person.013174754337.67", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013174754337.67"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "National Technical University of Ukraine Kiev Polytechnic Institute", 
          "id": "https://www.grid.ac/institutes/grid.440544.5", 
          "name": [
            "\u201cKyiv Polytechnic Institute\u201d National Technical University of Ukraine, pr. Pobedy 37, 03056, Kiev, Ukraine"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Vas\u2019kevich", 
        "givenName": "A. I.", 
        "id": "sg:person.016422071357.41", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016422071357.41"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.464621.3", 
          "name": [
            "Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02094, Kiev, Ukraine"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Vovk", 
        "givenName": "M. V.", 
        "id": "sg:person.013407403301.91", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013407403301.91"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1002/ardp.2503240910", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1001573699"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/ardp.2503240910", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1001573699"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.ejmech.2005.02.010", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1007479249"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0960-894x(03)00587-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1013834467"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0960-894x(03)00587-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1013834467"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1134/s107042801212007x", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1015546484", 
          "https://doi.org/10.1134/s107042801212007x"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1134/s1070428015020165", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1029347378", 
          "https://doi.org/10.1134/s1070428015020165"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0960-894x(00)00084-6", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1041483085"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmcl.2003.10.062", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1045455687"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c3ra46606j", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1045482402"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1134/s1070428013080137", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1046677485", 
          "https://doi.org/10.1134/s1070428013080137"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jm030287l", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055948029"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jm030287l", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055948029"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1055/s-2002-31963", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1057414969"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3987/com-98-8104", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1071773867"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://app.dimensions.ai/details/publication/pub.1074354274", 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.24959/ophcj.15.870", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1093146949"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2016-07", 
    "datePublishedReg": "2016-07-01", 
    "description": "Intramolecular cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides on heating in polyphosphoric acid afforded 8-aryl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones and 5-aryl-1-(thiophen-3-yl)pyrrolidin-2-ones. Cyclofunctionalization of the title compounds with (chlorosulfanyl)benzene and 4-(chlorosulfanyl)-toluene led to the formation of 8-aryl-7-arylsulfanyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones or their mixtures with 5-aryl-4-arylsulfanyltetrahydrofuran-2-ones. 1-(Chlorosulfanyl)-4-nitrobenzene reacted with 4-(4-methylphenyl)-N-(thiophen-3-yl)but-3-enamide and 4-(4-fluorophenyl)-N-(thiophen-3-yl)but-3-enamide to give 5-(4-methylphenyl)-4-(4-nitrophenylsulfanyl)-1-(thiophen-3-yl)pyrrolidin-2-one and 5-(4-fluorophenyl)-4-(4-nitrophenylsulfanyl)tetrahydrofuran-2-one, respectively.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1134/s1070428016070113", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1136317", 
        "issn": [
          "1070-4280", 
          "1608-3393"
        ], 
        "name": "Russian Journal of Organic Chemistry", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "7", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "52"
      }
    ], 
    "name": "Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes", 
    "pagination": "987-992", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "a99b66bdbd1fbba261fd9fba54a5661cebd7b8938f2e3881fb28bcd435780c76"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1134/s1070428016070113"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1035604519"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1134/s1070428016070113", 
      "https://app.dimensions.ai/details/publication/pub.1035604519"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T13:11", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000367_0000000367/records_88255_00000000.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://link.springer.com/10.1134%2FS1070428016070113"
  }
]
 

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/s1070428016070113'

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/s1070428016070113'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1134/s1070428016070113'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1134/s1070428016070113'


 

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

130 TRIPLES      21 PREDICATES      41 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1134/s1070428016070113 schema:about anzsrc-for:03
2 anzsrc-for:0305
3 schema:author N274a5b7cb33c40269184da162a701f82
4 schema:citation sg:pub.10.1134/s107042801212007x
5 sg:pub.10.1134/s1070428013080137
6 sg:pub.10.1134/s1070428015020165
7 https://app.dimensions.ai/details/publication/pub.1074354274
8 https://doi.org/10.1002/ardp.2503240910
9 https://doi.org/10.1016/j.bmcl.2003.10.062
10 https://doi.org/10.1016/j.ejmech.2005.02.010
11 https://doi.org/10.1016/s0960-894x(00)00084-6
12 https://doi.org/10.1016/s0960-894x(03)00587-0
13 https://doi.org/10.1021/jm030287l
14 https://doi.org/10.1039/c3ra46606j
15 https://doi.org/10.1055/s-2002-31963
16 https://doi.org/10.24959/ophcj.15.870
17 https://doi.org/10.3987/com-98-8104
18 schema:datePublished 2016-07
19 schema:datePublishedReg 2016-07-01
20 schema:description Intramolecular cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides on heating in polyphosphoric acid afforded 8-aryl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones and 5-aryl-1-(thiophen-3-yl)pyrrolidin-2-ones. Cyclofunctionalization of the title compounds with (chlorosulfanyl)benzene and 4-(chlorosulfanyl)-toluene led to the formation of 8-aryl-7-arylsulfanyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-ones or their mixtures with 5-aryl-4-arylsulfanyltetrahydrofuran-2-ones. 1-(Chlorosulfanyl)-4-nitrobenzene reacted with 4-(4-methylphenyl)-N-(thiophen-3-yl)but-3-enamide and 4-(4-fluorophenyl)-N-(thiophen-3-yl)but-3-enamide to give 5-(4-methylphenyl)-4-(4-nitrophenylsulfanyl)-1-(thiophen-3-yl)pyrrolidin-2-one and 5-(4-fluorophenyl)-4-(4-nitrophenylsulfanyl)tetrahydrofuran-2-one, respectively.
21 schema:genre research_article
22 schema:inLanguage en
23 schema:isAccessibleForFree false
24 schema:isPartOf N5a85abc3984845aebffcc95bdc00b6b6
25 N826fc70182f84ad5801784fa26b367a0
26 sg:journal.1136317
27 schema:name Electrophilic intramolecular cyclization of functional derivatives of unsaturated compounds: VIII. Cyclization of 4-aryl-N-(thiophen-3-yl)but-3-enamides by the action of polyphosphoric acid and chlorosulfanylarenes
28 schema:pagination 987-992
29 schema:productId N6df8a24adc194e43b6b000f3c52f6b85
30 N9e61644627b147d39f8537ea76e70a73
31 Nab33c884424d4f69b9b5d8f369aa84d6
32 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035604519
33 https://doi.org/10.1134/s1070428016070113
34 schema:sdDatePublished 2019-04-11T13:11
35 schema:sdLicense https://scigraph.springernature.com/explorer/license/
36 schema:sdPublisher Nbea131be26764041aa34581ae4dbecf9
37 schema:url https://link.springer.com/10.1134%2FS1070428016070113
38 sgo:license sg:explorer/license/
39 sgo:sdDataset articles
40 rdf:type schema:ScholarlyArticle
41 N274a5b7cb33c40269184da162a701f82 rdf:first sg:person.016325116525.94
42 rdf:rest N60d1c6c79c374adf90354cdb2c28796a
43 N36c2bd86029c45e68a0290559c3a70e3 rdf:first sg:person.016422071357.41
44 rdf:rest Na64eda10d8dd4a6fb597aadbda486366
45 N5a85abc3984845aebffcc95bdc00b6b6 schema:volumeNumber 52
46 rdf:type schema:PublicationVolume
47 N60d1c6c79c374adf90354cdb2c28796a rdf:first sg:person.013174754337.67
48 rdf:rest N36c2bd86029c45e68a0290559c3a70e3
49 N6df8a24adc194e43b6b000f3c52f6b85 schema:name readcube_id
50 schema:value a99b66bdbd1fbba261fd9fba54a5661cebd7b8938f2e3881fb28bcd435780c76
51 rdf:type schema:PropertyValue
52 N826fc70182f84ad5801784fa26b367a0 schema:issueNumber 7
53 rdf:type schema:PublicationIssue
54 N9e61644627b147d39f8537ea76e70a73 schema:name doi
55 schema:value 10.1134/s1070428016070113
56 rdf:type schema:PropertyValue
57 Na64eda10d8dd4a6fb597aadbda486366 rdf:first sg:person.013407403301.91
58 rdf:rest rdf:nil
59 Nab33c884424d4f69b9b5d8f369aa84d6 schema:name dimensions_id
60 schema:value pub.1035604519
61 rdf:type schema:PropertyValue
62 Nbea131be26764041aa34581ae4dbecf9 schema:name Springer Nature - SN SciGraph project
63 rdf:type schema:Organization
64 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
65 schema:name Chemical Sciences
66 rdf:type schema:DefinedTerm
67 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
68 schema:name Organic Chemistry
69 rdf:type schema:DefinedTerm
70 sg:journal.1136317 schema:issn 1070-4280
71 1608-3393
72 schema:name Russian Journal of Organic Chemistry
73 rdf:type schema:Periodical
74 sg:person.013174754337.67 schema:affiliation https://www.grid.ac/institutes/grid.464621.3
75 schema:familyName Vas’kevich
76 schema:givenName R. I.
77 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013174754337.67
78 rdf:type schema:Person
79 sg:person.013407403301.91 schema:affiliation https://www.grid.ac/institutes/grid.464621.3
80 schema:familyName Vovk
81 schema:givenName M. V.
82 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013407403301.91
83 rdf:type schema:Person
84 sg:person.016325116525.94 schema:affiliation https://www.grid.ac/institutes/grid.464621.3
85 schema:familyName Danilyuk
86 schema:givenName I. Yu.
87 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016325116525.94
88 rdf:type schema:Person
89 sg:person.016422071357.41 schema:affiliation https://www.grid.ac/institutes/grid.440544.5
90 schema:familyName Vas’kevich
91 schema:givenName A. I.
92 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016422071357.41
93 rdf:type schema:Person
94 sg:pub.10.1134/s107042801212007x schema:sameAs https://app.dimensions.ai/details/publication/pub.1015546484
95 https://doi.org/10.1134/s107042801212007x
96 rdf:type schema:CreativeWork
97 sg:pub.10.1134/s1070428013080137 schema:sameAs https://app.dimensions.ai/details/publication/pub.1046677485
98 https://doi.org/10.1134/s1070428013080137
99 rdf:type schema:CreativeWork
100 sg:pub.10.1134/s1070428015020165 schema:sameAs https://app.dimensions.ai/details/publication/pub.1029347378
101 https://doi.org/10.1134/s1070428015020165
102 rdf:type schema:CreativeWork
103 https://app.dimensions.ai/details/publication/pub.1074354274 schema:CreativeWork
104 https://doi.org/10.1002/ardp.2503240910 schema:sameAs https://app.dimensions.ai/details/publication/pub.1001573699
105 rdf:type schema:CreativeWork
106 https://doi.org/10.1016/j.bmcl.2003.10.062 schema:sameAs https://app.dimensions.ai/details/publication/pub.1045455687
107 rdf:type schema:CreativeWork
108 https://doi.org/10.1016/j.ejmech.2005.02.010 schema:sameAs https://app.dimensions.ai/details/publication/pub.1007479249
109 rdf:type schema:CreativeWork
110 https://doi.org/10.1016/s0960-894x(00)00084-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1041483085
111 rdf:type schema:CreativeWork
112 https://doi.org/10.1016/s0960-894x(03)00587-0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1013834467
113 rdf:type schema:CreativeWork
114 https://doi.org/10.1021/jm030287l schema:sameAs https://app.dimensions.ai/details/publication/pub.1055948029
115 rdf:type schema:CreativeWork
116 https://doi.org/10.1039/c3ra46606j schema:sameAs https://app.dimensions.ai/details/publication/pub.1045482402
117 rdf:type schema:CreativeWork
118 https://doi.org/10.1055/s-2002-31963 schema:sameAs https://app.dimensions.ai/details/publication/pub.1057414969
119 rdf:type schema:CreativeWork
120 https://doi.org/10.24959/ophcj.15.870 schema:sameAs https://app.dimensions.ai/details/publication/pub.1093146949
121 rdf:type schema:CreativeWork
122 https://doi.org/10.3987/com-98-8104 schema:sameAs https://app.dimensions.ai/details/publication/pub.1071773867
123 rdf:type schema:CreativeWork
124 https://www.grid.ac/institutes/grid.440544.5 schema:alternateName National Technical University of Ukraine Kiev Polytechnic Institute
125 schema:name “Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Pobedy 37, 03056, Kiev, Ukraine
126 rdf:type schema:Organization
127 https://www.grid.ac/institutes/grid.464621.3 schema:alternateName Institute of Organic Chemistry
128 schema:name Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, 02094, Kiev, Ukraine
129 “Enamine” Scientific Production Association, ul. Chervonotkats’ka 78, 02094, Kiev, Ukraine
130 rdf:type schema:Organization
 




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


...