Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2011-11

AUTHORS

A. T. Soldatenkov, S. A. Soldatova, R. R. Suleimanov, K. B. Polyanskii, V. E. Kotsyuba, A. F. Smol’yakov, V. N. Khrustalev, M. Yu. Antipin

ABSTRACT

The reaction of N-methyl-N-(diethoxycarbonyl)methyltetrahydropyridinium bromide with dimethyl acetylenedicarboxylate in the presence of triethylamine at room temperature afforded 1,2-dimethyl 1-ethyl 2-[(3-vinyl-1-methyl-3-phenyl-2-ethoxycarbonyl)pyrrolidin-2-yl]-ethene-1,1,2-tricarboxylate in 25% yield. Its structure was proved by XRD analysis. At cooling to −20°C the pyrrolidine yield signifi cantly decreased and 3,4-dimethyl 2,2-diethyl 1-methyl-7-phenyl-1,5,8,9-tetrahydro-2H-azonine-2,2,3,4-tetratcarboxylate was obtained in 31% yield.

PAGES

1738-1741

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428011110157

DOI

http://dx.doi.org/10.1134/s1070428011110157

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1023875449


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/2008/0607", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Plant Biology", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/06", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Biological Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Peoples' Friendship University of Russia", 
          "id": "https://www.grid.ac/institutes/grid.77642.30", 
          "name": [
            "Russian University of Peoples Friendship, 117198, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Soldatenkov", 
        "givenName": "A. T.", 
        "id": "sg:person.01111336752.76", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01111336752.76"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Peoples' Friendship University of Russia", 
          "id": "https://www.grid.ac/institutes/grid.77642.30", 
          "name": [
            "Russian University of Peoples Friendship, 117198, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Soldatova", 
        "givenName": "S. A.", 
        "id": "sg:person.013467155551.00", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013467155551.00"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Peoples' Friendship University of Russia", 
          "id": "https://www.grid.ac/institutes/grid.77642.30", 
          "name": [
            "Russian University of Peoples Friendship, 117198, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Suleimanov", 
        "givenName": "R. R.", 
        "id": "sg:person.014330403325.51", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014330403325.51"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Peoples' Friendship University of Russia", 
          "id": "https://www.grid.ac/institutes/grid.77642.30", 
          "name": [
            "Russian University of Peoples Friendship, 117198, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Polyanskii", 
        "givenName": "K. B.", 
        "id": "sg:person.015522506255.47", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015522506255.47"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Peoples' Friendship University of Russia", 
          "id": "https://www.grid.ac/institutes/grid.77642.30", 
          "name": [
            "Russian University of Peoples Friendship, 117198, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Kotsyuba", 
        "givenName": "V. E.", 
        "id": "sg:person.013775571407.62", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013775571407.62"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "A. N. Nesmeyanov Institute of Organoelement Compounds", 
          "id": "https://www.grid.ac/institutes/grid.431939.5", 
          "name": [
            "Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Smol\u2019yakov", 
        "givenName": "A. F.", 
        "id": "sg:person.014573152007.45", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014573152007.45"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "A. N. Nesmeyanov Institute of Organoelement Compounds", 
          "id": "https://www.grid.ac/institutes/grid.431939.5", 
          "name": [
            "Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Khrustalev", 
        "givenName": "V. N.", 
        "id": "sg:person.010615624362.70", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010615624362.70"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "A. N. Nesmeyanov Institute of Organoelement Compounds", 
          "id": "https://www.grid.ac/institutes/grid.431939.5", 
          "name": [
            "Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Antipin", 
        "givenName": "M. Yu.", 
        "id": "sg:person.010142146727.55", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010142146727.55"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1107/s0108767307043930", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027786902"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ja01583a048", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055809736"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2011-11", 
    "datePublishedReg": "2011-11-01", 
    "description": "The reaction of N-methyl-N-(diethoxycarbonyl)methyltetrahydropyridinium bromide with dimethyl acetylenedicarboxylate in the presence of triethylamine at room temperature afforded 1,2-dimethyl 1-ethyl 2-[(3-vinyl-1-methyl-3-phenyl-2-ethoxycarbonyl)pyrrolidin-2-yl]-ethene-1,1,2-tricarboxylate in 25% yield. Its structure was proved by XRD analysis. At cooling to \u221220\u00b0C the pyrrolidine yield signifi cantly decreased and 3,4-dimethyl 2,2-diethyl 1-methyl-7-phenyl-1,5,8,9-tetrahydro-2H-azonine-2,2,3,4-tetratcarboxylate was obtained in 31% yield.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1134/s1070428011110157", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1136317", 
        "issn": [
          "1070-4280", 
          "1608-3393"
        ], 
        "name": "Russian Journal of Organic Chemistry", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "11", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "47"
      }
    ], 
    "name": "Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate", 
    "pagination": "1738-1741", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "71bf158184beee0305e4606bc61459a0777c5af595084e481d508b6f1fd6e060"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1134/s1070428011110157"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1023875449"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1134/s1070428011110157", 
      "https://app.dimensions.ai/details/publication/pub.1023875449"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-10T20:41", 
    "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/v90/0000000001_0000000264/records_8684_00000488.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "http://link.springer.com/10.1134/S1070428011110157"
  }
]
 

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/s1070428011110157'

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/s1070428011110157'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1134/s1070428011110157'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1134/s1070428011110157'


 

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

119 TRIPLES      21 PREDICATES      29 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1134/s1070428011110157 schema:about anzsrc-for:06
2 anzsrc-for:0607
3 schema:author N011a6a18233349b486bca7f1581d9ff7
4 schema:citation https://doi.org/10.1021/ja01583a048
5 https://doi.org/10.1107/s0108767307043930
6 schema:datePublished 2011-11
7 schema:datePublishedReg 2011-11-01
8 schema:description The reaction of N-methyl-N-(diethoxycarbonyl)methyltetrahydropyridinium bromide with dimethyl acetylenedicarboxylate in the presence of triethylamine at room temperature afforded 1,2-dimethyl 1-ethyl 2-[(3-vinyl-1-methyl-3-phenyl-2-ethoxycarbonyl)pyrrolidin-2-yl]-ethene-1,1,2-tricarboxylate in 25% yield. Its structure was proved by XRD analysis. At cooling to −20°C the pyrrolidine yield signifi cantly decreased and 3,4-dimethyl 2,2-diethyl 1-methyl-7-phenyl-1,5,8,9-tetrahydro-2H-azonine-2,2,3,4-tetratcarboxylate was obtained in 31% yield.
9 schema:genre research_article
10 schema:inLanguage en
11 schema:isAccessibleForFree false
12 schema:isPartOf N5d58ba1676194f88ac0735692ffa17d6
13 Nd37cc2161bb742cc8bfba6ee1be5aabb
14 sg:journal.1136317
15 schema:name Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate
16 schema:pagination 1738-1741
17 schema:productId N166db1bf88044026b9feac1d9a9bb044
18 N5db5435d3d024f34bc064c69863783a2
19 Neb5a10c2fb7a4257b76b55784ecdeb13
20 schema:sameAs https://app.dimensions.ai/details/publication/pub.1023875449
21 https://doi.org/10.1134/s1070428011110157
22 schema:sdDatePublished 2019-04-10T20:41
23 schema:sdLicense https://scigraph.springernature.com/explorer/license/
24 schema:sdPublisher N8614a60ce3c845749c00f5f5090c0d8b
25 schema:url http://link.springer.com/10.1134/S1070428011110157
26 sgo:license sg:explorer/license/
27 sgo:sdDataset articles
28 rdf:type schema:ScholarlyArticle
29 N011a6a18233349b486bca7f1581d9ff7 rdf:first sg:person.01111336752.76
30 rdf:rest N5b062d6cc9314c4c8fd788ae90b61464
31 N166db1bf88044026b9feac1d9a9bb044 schema:name readcube_id
32 schema:value 71bf158184beee0305e4606bc61459a0777c5af595084e481d508b6f1fd6e060
33 rdf:type schema:PropertyValue
34 N22e35c8cd34f4c1596b5f13e0b0492c9 rdf:first sg:person.013775571407.62
35 rdf:rest N7fffa226021d465e9f0291d7c4e6809a
36 N46d724e1c027427cb83a36ec9681c1e3 rdf:first sg:person.010615624362.70
37 rdf:rest Ne0feedabcbe74a8cbb6211632ad98616
38 N5b062d6cc9314c4c8fd788ae90b61464 rdf:first sg:person.013467155551.00
39 rdf:rest Nfdbe8947b5544f77815752294413221d
40 N5d58ba1676194f88ac0735692ffa17d6 schema:issueNumber 11
41 rdf:type schema:PublicationIssue
42 N5db5435d3d024f34bc064c69863783a2 schema:name dimensions_id
43 schema:value pub.1023875449
44 rdf:type schema:PropertyValue
45 N7fffa226021d465e9f0291d7c4e6809a rdf:first sg:person.014573152007.45
46 rdf:rest N46d724e1c027427cb83a36ec9681c1e3
47 N8614a60ce3c845749c00f5f5090c0d8b schema:name Springer Nature - SN SciGraph project
48 rdf:type schema:Organization
49 Nb66c05838dc144a1ab423b87fbadf6fa rdf:first sg:person.015522506255.47
50 rdf:rest N22e35c8cd34f4c1596b5f13e0b0492c9
51 Nd37cc2161bb742cc8bfba6ee1be5aabb schema:volumeNumber 47
52 rdf:type schema:PublicationVolume
53 Ne0feedabcbe74a8cbb6211632ad98616 rdf:first sg:person.010142146727.55
54 rdf:rest rdf:nil
55 Neb5a10c2fb7a4257b76b55784ecdeb13 schema:name doi
56 schema:value 10.1134/s1070428011110157
57 rdf:type schema:PropertyValue
58 Nfdbe8947b5544f77815752294413221d rdf:first sg:person.014330403325.51
59 rdf:rest Nb66c05838dc144a1ab423b87fbadf6fa
60 anzsrc-for:06 schema:inDefinedTermSet anzsrc-for:
61 schema:name Biological Sciences
62 rdf:type schema:DefinedTerm
63 anzsrc-for:0607 schema:inDefinedTermSet anzsrc-for:
64 schema:name Plant Biology
65 rdf:type schema:DefinedTerm
66 sg:journal.1136317 schema:issn 1070-4280
67 1608-3393
68 schema:name Russian Journal of Organic Chemistry
69 rdf:type schema:Periodical
70 sg:person.010142146727.55 schema:affiliation https://www.grid.ac/institutes/grid.431939.5
71 schema:familyName Antipin
72 schema:givenName M. Yu.
73 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010142146727.55
74 rdf:type schema:Person
75 sg:person.010615624362.70 schema:affiliation https://www.grid.ac/institutes/grid.431939.5
76 schema:familyName Khrustalev
77 schema:givenName V. N.
78 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010615624362.70
79 rdf:type schema:Person
80 sg:person.01111336752.76 schema:affiliation https://www.grid.ac/institutes/grid.77642.30
81 schema:familyName Soldatenkov
82 schema:givenName A. T.
83 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01111336752.76
84 rdf:type schema:Person
85 sg:person.013467155551.00 schema:affiliation https://www.grid.ac/institutes/grid.77642.30
86 schema:familyName Soldatova
87 schema:givenName S. A.
88 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013467155551.00
89 rdf:type schema:Person
90 sg:person.013775571407.62 schema:affiliation https://www.grid.ac/institutes/grid.77642.30
91 schema:familyName Kotsyuba
92 schema:givenName V. E.
93 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013775571407.62
94 rdf:type schema:Person
95 sg:person.014330403325.51 schema:affiliation https://www.grid.ac/institutes/grid.77642.30
96 schema:familyName Suleimanov
97 schema:givenName R. R.
98 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014330403325.51
99 rdf:type schema:Person
100 sg:person.014573152007.45 schema:affiliation https://www.grid.ac/institutes/grid.431939.5
101 schema:familyName Smol’yakov
102 schema:givenName A. F.
103 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014573152007.45
104 rdf:type schema:Person
105 sg:person.015522506255.47 schema:affiliation https://www.grid.ac/institutes/grid.77642.30
106 schema:familyName Polyanskii
107 schema:givenName K. B.
108 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015522506255.47
109 rdf:type schema:Person
110 https://doi.org/10.1021/ja01583a048 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055809736
111 rdf:type schema:CreativeWork
112 https://doi.org/10.1107/s0108767307043930 schema:sameAs https://app.dimensions.ai/details/publication/pub.1027786902
113 rdf:type schema:CreativeWork
114 https://www.grid.ac/institutes/grid.431939.5 schema:alternateName A. N. Nesmeyanov Institute of Organoelement Compounds
115 schema:name Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia
116 rdf:type schema:Organization
117 https://www.grid.ac/institutes/grid.77642.30 schema:alternateName Peoples' Friendship University of Russia
118 schema:name Russian University of Peoples Friendship, 117198, Moscow, Russia
119 rdf:type schema:Organization
 




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


...