Chirally N-Substituted Indole-2-carbaldehydes. Preparation and Use in Asymmetric Synthesis View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2005-10

AUTHORS

N. E. Golantsov, A. V. Karchava, Z. A. Starikova, F. M. Dolgushin, M. A. Yurovskaya

ABSTRACT

A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied. The structure of the major diastereomer of (2R′)-1-phenyl-2-[1-((1R′)-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor diastereomer (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively were established by X-ray analysis. More... »

PAGES

1290-1299

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10593-005-0315-0

DOI

http://dx.doi.org/10.1007/s10593-005-0315-0

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1044563668


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": "M. V. Lomonosov State University, 119234, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/grid.14476.30", 
          "name": [
            "M. V. Lomonosov State University, 119234, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Golantsov", 
        "givenName": "N. E.", 
        "id": "sg:person.016540103521.34", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016540103521.34"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "M. V. Lomonosov State University, 119234, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/grid.14476.30", 
          "name": [
            "M. V. Lomonosov State University, 119234, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Karchava", 
        "givenName": "A. V.", 
        "id": "sg:person.016377145165.12", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016377145165.12"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/grid.431939.5", 
          "name": [
            "A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Starikova", 
        "givenName": "Z. A.", 
        "id": "sg:person.014473641160.05", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014473641160.05"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/grid.431939.5", 
          "name": [
            "A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Dolgushin", 
        "givenName": "F. M.", 
        "id": "sg:person.01267101640.70", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01267101640.70"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "M. V. Lomonosov State University, 119234, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/grid.14476.30", 
          "name": [
            "M. V. Lomonosov State University, 119234, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Yurovskaya", 
        "givenName": "M. A.", 
        "id": "sg:person.01266162477.33", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01266162477.33"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/pl00000092", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1014595616", 
          "https://doi.org/10.1007/pl00000092"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2005-10", 
    "datePublishedReg": "2005-10-01", 
    "description": "A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied. The structure of the major diastereomer of (2R\u2032)-1-phenyl-2-[1-((1R\u2032)-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor diastereomer (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively were established by X-ray analysis.", 
    "genre": "article", 
    "id": "sg:pub.10.1007/s10593-005-0315-0", 
    "inLanguage": "en", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1358699", 
        "issn": [
          "0132-6244", 
          "1573-8353"
        ], 
        "name": "Chemistry of Heterocyclic Compounds", 
        "publisher": "Springer Nature", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "10", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "41"
      }
    ], 
    "keywords": [
      "active secondary alcohols", 
      "asymmetric synthesis", 
      "Danishefsky's diene", 
      "cyano group", 
      "minor diastereomer", 
      "secondary alcohols", 
      "major diastereomer", 
      "ray analysis", 
      "aromatic amines", 
      "indole-2-carbaldehydes", 
      "aldehydes", 
      "diastereomers", 
      "synthesis", 
      "subsequent reduction", 
      "reaction", 
      "simple method", 
      "imines", 
      "alkylation", 
      "amines", 
      "dienes", 
      "preparation", 
      "alcohol", 
      "structure", 
      "method", 
      "reduction", 
      "group", 
      "analysis", 
      "use", 
      "active indole-2-carbaldehydes", 
      "Substituted Indole-2-carbaldehydes"
    ], 
    "name": "Chirally N-Substituted Indole-2-carbaldehydes. Preparation and Use in Asymmetric Synthesis", 
    "pagination": "1290-1299", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1044563668"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s10593-005-0315-0"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s10593-005-0315-0", 
      "https://app.dimensions.ai/details/publication/pub.1044563668"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2021-12-01T19:16", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20211201/entities/gbq_results/article/article_398.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1007/s10593-005-0315-0"
  }
]
 

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/s10593-005-0315-0'

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/s10593-005-0315-0'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s10593-005-0315-0'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s10593-005-0315-0'


 

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

123 TRIPLES      22 PREDICATES      57 URIs      48 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s10593-005-0315-0 schema:about anzsrc-for:03
2 anzsrc-for:0305
3 schema:author N18dfec551a474165a3ebb7699a892d62
4 schema:citation sg:pub.10.1007/pl00000092
5 schema:datePublished 2005-10
6 schema:datePublishedReg 2005-10-01
7 schema:description A simple method is proposed for the synthesis of optically active indole-2-carbaldehydes via alkylation of 2-cyanoindole by optically active secondary alcohols and subsequent reduction of the cyano group to an aldehyde. Reaction of the aldehydes obtained with aromatic amines gave imines whose reaction with the Danishefsky diene was studied. The structure of the major diastereomer of (2R′)-1-phenyl-2-[1-((1R′)-1-phenylethyl)indol-2-yl]-1,2,3,4-tetrahydropyridine-4-one and minor diastereomer (2S)-2-[1-((1S)-2-methoxy-1-phenylethyl)indol-2-yl]-1-phenyl-1,2,3,4-tetrahydropyridine-4-one respectively were established by X-ray analysis.
8 schema:genre article
9 schema:inLanguage en
10 schema:isAccessibleForFree false
11 schema:isPartOf N02b14867c60d47838e8618569c345caf
12 N27630102f6094ceba3dff66ac7d99f8f
13 sg:journal.1358699
14 schema:keywords Danishefsky's diene
15 Substituted Indole-2-carbaldehydes
16 active indole-2-carbaldehydes
17 active secondary alcohols
18 alcohol
19 aldehydes
20 alkylation
21 amines
22 analysis
23 aromatic amines
24 asymmetric synthesis
25 cyano group
26 diastereomers
27 dienes
28 group
29 imines
30 indole-2-carbaldehydes
31 major diastereomer
32 method
33 minor diastereomer
34 preparation
35 ray analysis
36 reaction
37 reduction
38 secondary alcohols
39 simple method
40 structure
41 subsequent reduction
42 synthesis
43 use
44 schema:name Chirally N-Substituted Indole-2-carbaldehydes. Preparation and Use in Asymmetric Synthesis
45 schema:pagination 1290-1299
46 schema:productId N20c13f01215549eb8554a488079536d5
47 N68771ca6031b4f359ba46b4b7baa586d
48 schema:sameAs https://app.dimensions.ai/details/publication/pub.1044563668
49 https://doi.org/10.1007/s10593-005-0315-0
50 schema:sdDatePublished 2021-12-01T19:16
51 schema:sdLicense https://scigraph.springernature.com/explorer/license/
52 schema:sdPublisher N3f2954db8cbf48398520e4ac1885a538
53 schema:url https://doi.org/10.1007/s10593-005-0315-0
54 sgo:license sg:explorer/license/
55 sgo:sdDataset articles
56 rdf:type schema:ScholarlyArticle
57 N02b14867c60d47838e8618569c345caf schema:issueNumber 10
58 rdf:type schema:PublicationIssue
59 N0d7101bcb5024f20a325489fd4402c5d rdf:first sg:person.01266162477.33
60 rdf:rest rdf:nil
61 N18dfec551a474165a3ebb7699a892d62 rdf:first sg:person.016540103521.34
62 rdf:rest N4d5a659827564402bc81bf2240a71b7f
63 N20497e0d7b6946e4b4f7e14c409c2cdd rdf:first sg:person.014473641160.05
64 rdf:rest Na19e3379db0d48f8925f6a1cb709a446
65 N20c13f01215549eb8554a488079536d5 schema:name dimensions_id
66 schema:value pub.1044563668
67 rdf:type schema:PropertyValue
68 N27630102f6094ceba3dff66ac7d99f8f schema:volumeNumber 41
69 rdf:type schema:PublicationVolume
70 N3f2954db8cbf48398520e4ac1885a538 schema:name Springer Nature - SN SciGraph project
71 rdf:type schema:Organization
72 N4d5a659827564402bc81bf2240a71b7f rdf:first sg:person.016377145165.12
73 rdf:rest N20497e0d7b6946e4b4f7e14c409c2cdd
74 N68771ca6031b4f359ba46b4b7baa586d schema:name doi
75 schema:value 10.1007/s10593-005-0315-0
76 rdf:type schema:PropertyValue
77 Na19e3379db0d48f8925f6a1cb709a446 rdf:first sg:person.01267101640.70
78 rdf:rest N0d7101bcb5024f20a325489fd4402c5d
79 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
80 schema:name Chemical Sciences
81 rdf:type schema:DefinedTerm
82 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
83 schema:name Organic Chemistry
84 rdf:type schema:DefinedTerm
85 sg:journal.1358699 schema:issn 0132-6244
86 1573-8353
87 schema:name Chemistry of Heterocyclic Compounds
88 schema:publisher Springer Nature
89 rdf:type schema:Periodical
90 sg:person.01266162477.33 schema:affiliation grid-institutes:grid.14476.30
91 schema:familyName Yurovskaya
92 schema:givenName M. A.
93 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01266162477.33
94 rdf:type schema:Person
95 sg:person.01267101640.70 schema:affiliation grid-institutes:grid.431939.5
96 schema:familyName Dolgushin
97 schema:givenName F. M.
98 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01267101640.70
99 rdf:type schema:Person
100 sg:person.014473641160.05 schema:affiliation grid-institutes:grid.431939.5
101 schema:familyName Starikova
102 schema:givenName Z. A.
103 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014473641160.05
104 rdf:type schema:Person
105 sg:person.016377145165.12 schema:affiliation grid-institutes:grid.14476.30
106 schema:familyName Karchava
107 schema:givenName A. V.
108 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016377145165.12
109 rdf:type schema:Person
110 sg:person.016540103521.34 schema:affiliation grid-institutes:grid.14476.30
111 schema:familyName Golantsov
112 schema:givenName N. E.
113 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.016540103521.34
114 rdf:type schema:Person
115 sg:pub.10.1007/pl00000092 schema:sameAs https://app.dimensions.ai/details/publication/pub.1014595616
116 https://doi.org/10.1007/pl00000092
117 rdf:type schema:CreativeWork
118 grid-institutes:grid.14476.30 schema:alternateName M. V. Lomonosov State University, 119234, Moscow, Russia
119 schema:name M. V. Lomonosov State University, 119234, Moscow, Russia
120 rdf:type schema:Organization
121 grid-institutes:grid.431939.5 schema:alternateName A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia
122 schema:name A. N. Nesmeyanov Institute of Organoelement Compounds, 119991, Moscow, Russia
123 rdf:type schema:Organization
 




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


...