Quantum chemical studies of pyrimidin-4-ones 4.* Electronic structure and reactivity of substituted 2-oxo(thioxo)thieno[2,3-d]pyrimidin-4-ones. Mechanism of ipso-substitution of methyl group by ... View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2014-09

AUTHORS

M. Kh. Mamarahmonov, L. I. Belen’kii, N. D. Chuvylkin, M. A. Ashirmatov, B. Zh. Elmuradov, I. Ortikov, A. Kodirov, Kh. M. Shakhidoyatov

ABSTRACT

The quantum chemical calculations of the energies, electronic structures, and geometries for the products and intermediates of the ipso-nitration of 5,6-dimethyl-substituted 2-oxo- and 2-thioxothieno[2,3-d]pyrimidin-4-ones, as well as 6-methyl-5-nitrothieno[2,3-d]pyrimidin-4-one and 3,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid formed under the action of a nitrating mixture on 5,6-dimethylthieno[2,3-d]pyrimidin-4-one and 3,5,6-trimethylthieno[2,3-d]pyrimidin-4-one, respectively, were performed in terms of the HF and DFT (B3LYP) approximations in the 3-21G basis set. Taking into account the substituent effects in the pyrimidine cycle, solvents, and prototropic tautomerism, possible reasons for the predominant ipso-substitution of the methyl group at the C(5) atom by the nitro group of the thienopyrimidine system and differences in behavior of 3-unsubstituted and 3-substituted thieno[2,3-d]pyrimidin-4-ones were considered. More... »

PAGES

1986-1992

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-014-0689-1

DOI

http://dx.doi.org/10.1007/s11172-014-0689-1

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1025442953


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/2008/0202", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Atomic, Molecular, Nuclear, Particle and Plasma Physics", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/02", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Physical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "name": [
            "S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Mamarahmonov", 
        "givenName": "M. Kh.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Russian Academy of Sciences", 
          "id": "https://www.grid.ac/institutes/grid.4886.2", 
          "name": [
            "N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Belen\u2019kii", 
        "givenName": "L. I.", 
        "id": "sg:person.016614773551.45", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016614773551.45"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Russian Academy of Sciences", 
          "id": "https://www.grid.ac/institutes/grid.4886.2", 
          "name": [
            "N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Chuvylkin", 
        "givenName": "N. D.", 
        "id": "sg:person.010473055641.48", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010473055641.48"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ashirmatov", 
        "givenName": "M. A.", 
        "id": "sg:person.016557000703.78", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016557000703.78"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Elmuradov", 
        "givenName": "B. Zh.", 
        "id": "sg:person.016612326652.48", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016612326652.48"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ortikov", 
        "givenName": "I.", 
        "id": "sg:person.015557632307.94", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015557632307.94"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Karshi State University", 
          "id": "https://www.grid.ac/institutes/grid.444642.4", 
          "name": [
            "Karshi State University, Karshi, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Kodirov", 
        "givenName": "A.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "name": [
            "S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Shakhidoyatov", 
        "givenName": "Kh. M.", 
        "id": "sg:person.015706066705.62", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015706066705.62"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/s11172-014-0436-7", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1038761433", 
          "https://doi.org/10.1007/s11172-014-0436-7"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ja01310a035", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055791034"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ja01867a016", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055821021"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo981557o", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056039894"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo981557o", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056039894"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.9734/acsj/2013/4203", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1074126485"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2014-09", 
    "datePublishedReg": "2014-09-01", 
    "description": "The quantum chemical calculations of the energies, electronic structures, and geometries for the products and intermediates of the ipso-nitration of 5,6-dimethyl-substituted 2-oxo- and 2-thioxothieno[2,3-d]pyrimidin-4-ones, as well as 6-methyl-5-nitrothieno[2,3-d]pyrimidin-4-one and 3,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid formed under the action of a nitrating mixture on 5,6-dimethylthieno[2,3-d]pyrimidin-4-one and 3,5,6-trimethylthieno[2,3-d]pyrimidin-4-one, respectively, were performed in terms of the HF and DFT (B3LYP) approximations in the 3-21G basis set. Taking into account the substituent effects in the pyrimidine cycle, solvents, and prototropic tautomerism, possible reasons for the predominant ipso-substitution of the methyl group at the C(5) atom by the nitro group of the thienopyrimidine system and differences in behavior of 3-unsubstituted and 3-substituted thieno[2,3-d]pyrimidin-4-ones were considered.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1007/s11172-014-0689-1", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1022309", 
        "issn": [
          "1066-5285", 
          "1573-9171"
        ], 
        "name": "Russian Chemical Bulletin", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "9", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "63"
      }
    ], 
    "name": "Quantum chemical studies of pyrimidin-4-ones 4.* Electronic structure and reactivity of substituted 2-oxo(thioxo)thieno[2,3-d]pyrimidin-4-ones. Mechanism of ipso-substitution of methyl group by nitro group", 
    "pagination": "1986-1992", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "7936874532df7155c20d6ddc1d357b4565ad4f62b62cb29fecb15478cd822b0c"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s11172-014-0689-1"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1025442953"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s11172-014-0689-1", 
      "https://app.dimensions.ai/details/publication/pub.1025442953"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-10T19:12", 
    "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_8678_00000532.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "http://link.springer.com/10.1007%2Fs11172-014-0689-1"
  }
]
 

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/s11172-014-0689-1'

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/s11172-014-0689-1'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s11172-014-0689-1'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s11172-014-0689-1'


 

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

137 TRIPLES      21 PREDICATES      32 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s11172-014-0689-1 schema:about anzsrc-for:02
2 anzsrc-for:0202
3 schema:author N92db56e5fa454278bfac0b448ddabbd2
4 schema:citation sg:pub.10.1007/s11172-014-0436-7
5 https://doi.org/10.1021/ja01310a035
6 https://doi.org/10.1021/ja01867a016
7 https://doi.org/10.1021/jo981557o
8 https://doi.org/10.9734/acsj/2013/4203
9 schema:datePublished 2014-09
10 schema:datePublishedReg 2014-09-01
11 schema:description The quantum chemical calculations of the energies, electronic structures, and geometries for the products and intermediates of the ipso-nitration of 5,6-dimethyl-substituted 2-oxo- and 2-thioxothieno[2,3-d]pyrimidin-4-ones, as well as 6-methyl-5-nitrothieno[2,3-d]pyrimidin-4-one and 3,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid formed under the action of a nitrating mixture on 5,6-dimethylthieno[2,3-d]pyrimidin-4-one and 3,5,6-trimethylthieno[2,3-d]pyrimidin-4-one, respectively, were performed in terms of the HF and DFT (B3LYP) approximations in the 3-21G basis set. Taking into account the substituent effects in the pyrimidine cycle, solvents, and prototropic tautomerism, possible reasons for the predominant ipso-substitution of the methyl group at the C(5) atom by the nitro group of the thienopyrimidine system and differences in behavior of 3-unsubstituted and 3-substituted thieno[2,3-d]pyrimidin-4-ones were considered.
12 schema:genre research_article
13 schema:inLanguage en
14 schema:isAccessibleForFree false
15 schema:isPartOf N44fa091bb3f44fb6820f0cfedb5d86e4
16 N4887f6b57ca240248badaa01aa49f8f1
17 sg:journal.1022309
18 schema:name Quantum chemical studies of pyrimidin-4-ones 4.* Electronic structure and reactivity of substituted 2-oxo(thioxo)thieno[2,3-d]pyrimidin-4-ones. Mechanism of ipso-substitution of methyl group by nitro group
19 schema:pagination 1986-1992
20 schema:productId N2ced0f190b7147f89a780abd87e8156e
21 Nac9502544d1049dda5a527f06b0330b4
22 Ne055c5442a654c848da8f8954e09e8e7
23 schema:sameAs https://app.dimensions.ai/details/publication/pub.1025442953
24 https://doi.org/10.1007/s11172-014-0689-1
25 schema:sdDatePublished 2019-04-10T19:12
26 schema:sdLicense https://scigraph.springernature.com/explorer/license/
27 schema:sdPublisher N765571ca1c8c458f88753fc0a6ff855d
28 schema:url http://link.springer.com/10.1007%2Fs11172-014-0689-1
29 sgo:license sg:explorer/license/
30 sgo:sdDataset articles
31 rdf:type schema:ScholarlyArticle
32 N05539f39ea834581a75daddd499efcdd rdf:first sg:person.015557632307.94
33 rdf:rest N48a472a0acb3479596ff19a86c1f3fde
34 N0fd31ea241674b609423dbc8c6725f17 schema:name S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic
35 rdf:type schema:Organization
36 N2ced0f190b7147f89a780abd87e8156e schema:name readcube_id
37 schema:value 7936874532df7155c20d6ddc1d357b4565ad4f62b62cb29fecb15478cd822b0c
38 rdf:type schema:PropertyValue
39 N351eb76eb5bc4468b7ed63e3c15c2551 schema:affiliation N565f7b4890d14539abc6a23e503307ef
40 schema:familyName Mamarahmonov
41 schema:givenName M. Kh.
42 rdf:type schema:Person
43 N3809d5f4f6f548ac960a664d9a9d44f8 rdf:first sg:person.016557000703.78
44 rdf:rest Ndd6ffa727f0543fe91d5a51c48170ea4
45 N44fa091bb3f44fb6820f0cfedb5d86e4 schema:volumeNumber 63
46 rdf:type schema:PublicationVolume
47 N46425c1f6a73422c86bdbed3b4c8e72f rdf:first sg:person.010473055641.48
48 rdf:rest N3809d5f4f6f548ac960a664d9a9d44f8
49 N4887f6b57ca240248badaa01aa49f8f1 schema:issueNumber 9
50 rdf:type schema:PublicationIssue
51 N48a472a0acb3479596ff19a86c1f3fde rdf:first N6c6843b9e7c24594ae42161b5e09e365
52 rdf:rest Ned476fb6e88246fcb36d918f5480b4ad
53 N53a5862c52134259bf7b1166038ea5bd schema:name S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic
54 rdf:type schema:Organization
55 N565f7b4890d14539abc6a23e503307ef schema:name S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic
56 rdf:type schema:Organization
57 N5b9c2dc223794d929212413ac48c9009 schema:name S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic
58 rdf:type schema:Organization
59 N6c6843b9e7c24594ae42161b5e09e365 schema:affiliation https://www.grid.ac/institutes/grid.444642.4
60 schema:familyName Kodirov
61 schema:givenName A.
62 rdf:type schema:Person
63 N7022344425b24763a360e41dbdf357d1 rdf:first sg:person.016614773551.45
64 rdf:rest N46425c1f6a73422c86bdbed3b4c8e72f
65 N765571ca1c8c458f88753fc0a6ff855d schema:name Springer Nature - SN SciGraph project
66 rdf:type schema:Organization
67 N92db56e5fa454278bfac0b448ddabbd2 rdf:first N351eb76eb5bc4468b7ed63e3c15c2551
68 rdf:rest N7022344425b24763a360e41dbdf357d1
69 Nac9502544d1049dda5a527f06b0330b4 schema:name dimensions_id
70 schema:value pub.1025442953
71 rdf:type schema:PropertyValue
72 Ndd6ffa727f0543fe91d5a51c48170ea4 rdf:first sg:person.016612326652.48
73 rdf:rest N05539f39ea834581a75daddd499efcdd
74 Ne055c5442a654c848da8f8954e09e8e7 schema:name doi
75 schema:value 10.1007/s11172-014-0689-1
76 rdf:type schema:PropertyValue
77 Ned476fb6e88246fcb36d918f5480b4ad rdf:first sg:person.015706066705.62
78 rdf:rest rdf:nil
79 Nf09cbd5c886a4fd3befc669cc179478a schema:name S. Yu. Yunusov Institute of Plant Substances, Academy of Sciences of the Uzbekistan Republic, 77 ul. M. Ulugbeka, 100170, Tashkent, Uzbekistan Republic
80 rdf:type schema:Organization
81 anzsrc-for:02 schema:inDefinedTermSet anzsrc-for:
82 schema:name Physical Sciences
83 rdf:type schema:DefinedTerm
84 anzsrc-for:0202 schema:inDefinedTermSet anzsrc-for:
85 schema:name Atomic, Molecular, Nuclear, Particle and Plasma Physics
86 rdf:type schema:DefinedTerm
87 sg:journal.1022309 schema:issn 1066-5285
88 1573-9171
89 schema:name Russian Chemical Bulletin
90 rdf:type schema:Periodical
91 sg:person.010473055641.48 schema:affiliation https://www.grid.ac/institutes/grid.4886.2
92 schema:familyName Chuvylkin
93 schema:givenName N. D.
94 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010473055641.48
95 rdf:type schema:Person
96 sg:person.015557632307.94 schema:affiliation N5b9c2dc223794d929212413ac48c9009
97 schema:familyName Ortikov
98 schema:givenName I.
99 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015557632307.94
100 rdf:type schema:Person
101 sg:person.015706066705.62 schema:affiliation N0fd31ea241674b609423dbc8c6725f17
102 schema:familyName Shakhidoyatov
103 schema:givenName Kh. M.
104 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015706066705.62
105 rdf:type schema:Person
106 sg:person.016557000703.78 schema:affiliation Nf09cbd5c886a4fd3befc669cc179478a
107 schema:familyName Ashirmatov
108 schema:givenName M. A.
109 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016557000703.78
110 rdf:type schema:Person
111 sg:person.016612326652.48 schema:affiliation N53a5862c52134259bf7b1166038ea5bd
112 schema:familyName Elmuradov
113 schema:givenName B. Zh.
114 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016612326652.48
115 rdf:type schema:Person
116 sg:person.016614773551.45 schema:affiliation https://www.grid.ac/institutes/grid.4886.2
117 schema:familyName Belen’kii
118 schema:givenName L. I.
119 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016614773551.45
120 rdf:type schema:Person
121 sg:pub.10.1007/s11172-014-0436-7 schema:sameAs https://app.dimensions.ai/details/publication/pub.1038761433
122 https://doi.org/10.1007/s11172-014-0436-7
123 rdf:type schema:CreativeWork
124 https://doi.org/10.1021/ja01310a035 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055791034
125 rdf:type schema:CreativeWork
126 https://doi.org/10.1021/ja01867a016 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055821021
127 rdf:type schema:CreativeWork
128 https://doi.org/10.1021/jo981557o schema:sameAs https://app.dimensions.ai/details/publication/pub.1056039894
129 rdf:type schema:CreativeWork
130 https://doi.org/10.9734/acsj/2013/4203 schema:sameAs https://app.dimensions.ai/details/publication/pub.1074126485
131 rdf:type schema:CreativeWork
132 https://www.grid.ac/institutes/grid.444642.4 schema:alternateName Karshi State University
133 schema:name Karshi State University, Karshi, Uzbekistan Republic
134 rdf:type schema:Organization
135 https://www.grid.ac/institutes/grid.4886.2 schema:alternateName Russian Academy of Sciences
136 schema:name N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
137 rdf:type schema:Organization
 




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


...