Thia-prins bicyclization approach for the stereoselective synthesis of dithia- and azathia-bicycles.
Identifieur interne : 000319 ( Main/Exploration ); précédent : 000318; suivant : 000320Thia-prins bicyclization approach for the stereoselective synthesis of dithia- and azathia-bicycles.
Auteurs : RBID : pubmed:23679080English descriptors
- KwdEn :
- Aldehydes (chemistry), Catalysis, Cyclization, Indium (chemistry), Molecular Structure, Pyrans (chemical synthesis), Pyrroles (chemical synthesis), Stereoisomerism, Sulfhydryl Compounds (chemical synthesis), Sulfhydryl Compounds (chemistry), Sulfonamides (chemistry), Toluene (analogs & derivatives), Toluene (chemistry).
- MESH :
- chemical , analogs & derivatives : Toluene.
- chemical , chemical synthesis : Pyrans, Pyrroles, Sulfhydryl Compounds.
- chemical , chemistry : Aldehydes, Indium, Sulfhydryl Compounds, Sulfonamides, Toluene.
- Catalysis, Cyclization, Molecular Structure, Stereoisomerism.
Abstract
A novel thia-Prins bicyclization approach has been developed for the first time for the synthesis of hexahydro-2H-thieno[3,2-c]thiopyran derivatives from the coupling of homoallylic mercaptans such as hex-3-ene-1,6-dithiol with various aldehydes using 10 mol % InBr3 in dichloromethane with high selectivity. In addition, the coupling of (E)-N-(6-mercaptohex-3-enyl)-4-methylbenzenesulfonamide with aldedydes affords the corresponding N-tosyloctahydrothiopyrano[4,3-b]pyrrole derivatives in good yields. This reaction is a stereoselective affording trans-fused product from E-homoallyllic mercaptan and cis-fused product from Z-homoallyllic mercaptan.
DOI: 10.1021/jo400680w
PubMed: 23679080
Links toward previous steps (curation, corpus...)
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Thia-prins bicyclization approach for the stereoselective synthesis of dithia- and azathia-bicycles.</title><author><name sortKey="Reddy, B V Subba" uniqKey="Reddy B">B V Subba Reddy</name><affiliation wicri:level="1"><nlm:affiliation>Natural Product Chemistry, ‡Centre for Nuclear Magnetic Resonance, §Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology , Hyderabad 500 007, India.</nlm:affiliation><country xml:lang="fr">Inde</country><wicri:regionArea>Natural Product Chemistry, ‡Centre for Nuclear Magnetic Resonance, §Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology , Hyderabad 500 007</wicri:regionArea></affiliation></author><author><name sortKey="Venkateswarlu, A" uniqKey="Venkateswarlu A">A Venkateswarlu</name></author><author><name sortKey="Borkar, Prashant" uniqKey="Borkar P">Prashant Borkar</name></author><author><name sortKey="Yadav, J S" uniqKey="Yadav J">J S Yadav</name></author><author><name sortKey="Kanakaraju, M" uniqKey="Kanakaraju M">M Kanakaraju</name></author><author><name sortKey="Kunwar, A C" uniqKey="Kunwar A">A C Kunwar</name></author><author><name sortKey="Sridhar, B" uniqKey="Sridhar B">B Sridhar</name></author></titleStmt><publicationStmt><date when="2013">2013</date><idno type="doi">10.1021/jo400680w</idno><idno type="RBID">pubmed:23679080</idno><idno type="pmid">23679080</idno><idno type="wicri:Area/Main/Corpus">000616</idno><idno type="wicri:Area/Main/Curation">000616</idno><idno type="wicri:Area/Main/Exploration">000319</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldehydes (chemistry)</term><term>Catalysis</term><term>Cyclization</term><term>Indium (chemistry)</term><term>Molecular Structure</term><term>Pyrans (chemical synthesis)</term><term>Pyrroles (chemical synthesis)</term><term>Stereoisomerism</term><term>Sulfhydryl Compounds (chemical synthesis)</term><term>Sulfhydryl Compounds (chemistry)</term><term>Sulfonamides (chemistry)</term><term>Toluene (analogs & derivatives)</term><term>Toluene (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Toluene</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Pyrans</term><term>Pyrroles</term><term>Sulfhydryl Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Aldehydes</term><term>Indium</term><term>Sulfhydryl Compounds</term><term>Sulfonamides</term><term>Toluene</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Cyclization</term><term>Molecular Structure</term><term>Stereoisomerism</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A novel thia-Prins bicyclization approach has been developed for the first time for the synthesis of hexahydro-2H-thieno[3,2-c]thiopyran derivatives from the coupling of homoallylic mercaptans such as hex-3-ene-1,6-dithiol with various aldehydes using 10 mol % InBr3 in dichloromethane with high selectivity. In addition, the coupling of (E)-N-(6-mercaptohex-3-enyl)-4-methylbenzenesulfonamide with aldedydes affords the corresponding N-tosyloctahydrothiopyrano[4,3-b]pyrrole derivatives in good yields. This reaction is a stereoselective affording trans-fused product from E-homoallyllic mercaptan and cis-fused product from Z-homoallyllic mercaptan.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">23679080</PMID><DateCreated><Year>2013</Year><Month>06</Month><Day>21</Day></DateCreated><DateCompleted><Year>2014</Year><Month>01</Month><Day>16</Day></DateCompleted><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>78</Volume><Issue>12</Issue><PubDate><Year>2013</Year><Month>Jun</Month><Day>21</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Thia-prins bicyclization approach for the stereoselective synthesis of dithia- and azathia-bicycles.</ArticleTitle><Pagination><MedlinePgn>6303-8</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo400680w</ELocationID><Abstract><AbstractText>A novel thia-Prins bicyclization approach has been developed for the first time for the synthesis of hexahydro-2H-thieno[3,2-c]thiopyran derivatives from the coupling of homoallylic mercaptans such as hex-3-ene-1,6-dithiol with various aldehydes using 10 mol % InBr3 in dichloromethane with high selectivity. In addition, the coupling of (E)-N-(6-mercaptohex-3-enyl)-4-methylbenzenesulfonamide with aldedydes affords the corresponding N-tosyloctahydrothiopyrano[4,3-b]pyrrole derivatives in good yields. This reaction is a stereoselective affording trans-fused product from E-homoallyllic mercaptan and cis-fused product from Z-homoallyllic mercaptan.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Reddy</LastName><ForeName>B V Subba</ForeName><Initials>BV</Initials><Affiliation>Natural Product Chemistry, ‡Centre for Nuclear Magnetic Resonance, §Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology , Hyderabad 500 007, India.</Affiliation></Author><Author ValidYN="Y"><LastName>Venkateswarlu</LastName><ForeName>A</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Borkar</LastName><ForeName>Prashant</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Yadav</LastName><ForeName>J S</ForeName><Initials>JS</Initials></Author><Author ValidYN="Y"><LastName>Kanakaraju</LastName><ForeName>M</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Kunwar</LastName><ForeName>A C</ForeName><Initials>AC</Initials></Author><Author ValidYN="Y"><LastName>Sridhar</LastName><ForeName>B</ForeName><Initials>B</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2013</Year><Month>05</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Aldehydes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Pyrans</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Pyrroles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Sulfhydryl Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Sulfonamides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>indium bromide</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>thiopyran</NameOfSubstance></Chemical><Chemical><RegistryNumber>045A6V3VFX</RegistryNumber><NameOfSubstance>Indium</NameOfSubstance></Chemical><Chemical><RegistryNumber>3FPU23BG52</RegistryNumber><NameOfSubstance>Toluene</NameOfSubstance></Chemical><Chemical><RegistryNumber>I8266RI90M</RegistryNumber><NameOfSubstance>4-toluenesulfonamide</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Aldehydes</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Cyclization</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Pyrans</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Pyrroles</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Sulfhydryl Compounds</DescriptorName><QualifierName MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Sulfonamides</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Toluene</DescriptorName><QualifierName MajorTopicYN="Y">analogs & derivatives</QualifierName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2013</Year><Month>5</Month><Day>28</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2013</Year><Month>5</Month><Day>18</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2013</Year><Month>5</Month><Day>18</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>1</Month><Day>17</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo400680w</ArticleId><ArticleId IdType="pubmed">23679080</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=IndiumV2/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000319 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000319 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= *** parameter Area/wikiCode missing ***
|area= IndiumV2
|flux= Main
|étape= Exploration
|type= RBID
|clé= pubmed:23679080
|texte= Thia-prins bicyclization approach for the stereoselective synthesis of dithia- and azathia-bicycles.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:23679080" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a IndiumV2
| This area was generated with Dilib version V0.5.76. |  |