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Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles
Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of...
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| Published in: | Tetrahedron 2011-09, Vol.67 (38), p.7370-7378 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c330t-97b129ab626fe2b1a552be62d52b24d30acb2ecf7b18ab3f2af46c85ac3adc6b3 |
| container_end_page | 7378 |
| container_issue | 38 |
| container_start_page | 7370 |
| container_title | Tetrahedron |
| container_volume | 67 |
| creator | Semenov, Vyacheslav E. Krylova, Evgeniya S. Galyametdinova, Irina V. Chernova, Alla V. Kharlamov, Sergey V. Latypov, Shamil K. Reznik, Vladimir S. |
| description | Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with
m-CPBA, H
2O
2, and I
2.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.07.034 |
| format | article |
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m-CPBA, H
2O
2, and I
2.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.07.034</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Alkylation ; Heterocycles ; Heterocyclophanes ; Isomers ; Macrocyclic compounds ; Nuclear magnetic resonance ; Structure elucidation ; Synthesis (chemistry) ; Terminals ; Tetrahedrons ; Uracil ; Uracils</subject><ispartof>Tetrahedron, 2011-09, Vol.67 (38), p.7370-7378</ispartof><rights>2011 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c330t-97b129ab626fe2b1a552be62d52b24d30acb2ecf7b18ab3f2af46c85ac3adc6b3</citedby><cites>FETCH-LOGICAL-c330t-97b129ab626fe2b1a552be62d52b24d30acb2ecf7b18ab3f2af46c85ac3adc6b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Semenov, Vyacheslav E.</creatorcontrib><creatorcontrib>Krylova, Evgeniya S.</creatorcontrib><creatorcontrib>Galyametdinova, Irina V.</creatorcontrib><creatorcontrib>Chernova, Alla V.</creatorcontrib><creatorcontrib>Kharlamov, Sergey V.</creatorcontrib><creatorcontrib>Latypov, Shamil K.</creatorcontrib><creatorcontrib>Reznik, Vladimir S.</creatorcontrib><title>Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles</title><title>Tetrahedron</title><description>Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with
m-CPBA, H
2O
2, and I
2.
[Display omitted]</description><subject>Alkylation</subject><subject>Heterocycles</subject><subject>Heterocyclophanes</subject><subject>Isomers</subject><subject>Macrocyclic compounds</subject><subject>Nuclear magnetic resonance</subject><subject>Structure elucidation</subject><subject>Synthesis (chemistry)</subject><subject>Terminals</subject><subject>Tetrahedrons</subject><subject>Uracil</subject><subject>Uracils</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kEtPwzAQhC0EEqXwA7jlyCXBrzitOKGKl1SJA3C27M2Gusqj2G5R_j2G9MxptLvfrDRDyDWjBaNM3W6LiLHglLGCVgUV8oTMmFQyLyVTp2RGqaS5pJyek4sQtpQmkosZgbexjxsMLmSmrzOPBqI7uDhmQ5MZGKF18HfpDPjhOO-9AdeGzHpXf2Kdfbu4yRp3wLzDzqJPqw1GnHgMl-SsMW3Aq6POycfjw_vqOV-_Pr2s7tc5CEFjvqws40tjFVcNcstMWXKLitdJuKwFNWA5QpOwhbGi4aaRChalAWFqUFbMyc30d-eHrz2GqDsXANvW9Djsg2aVlKqSJasSyiY0hQrBY6N33nXGj5pR_Vuo3upUqP4tVNNKp0KT527yYMpwcOh1AIc9YO08QtT14P5x_wDkS4DZ</recordid><startdate>20110923</startdate><enddate>20110923</enddate><creator>Semenov, Vyacheslav E.</creator><creator>Krylova, Evgeniya S.</creator><creator>Galyametdinova, Irina V.</creator><creator>Chernova, Alla V.</creator><creator>Kharlamov, Sergey V.</creator><creator>Latypov, Shamil K.</creator><creator>Reznik, Vladimir S.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20110923</creationdate><title>Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles</title><author>Semenov, Vyacheslav E. ; Krylova, Evgeniya S. ; Galyametdinova, Irina V. ; Chernova, Alla V. ; Kharlamov, Sergey V. ; Latypov, Shamil K. ; Reznik, Vladimir S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-97b129ab626fe2b1a552be62d52b24d30acb2ecf7b18ab3f2af46c85ac3adc6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkylation</topic><topic>Heterocycles</topic><topic>Heterocyclophanes</topic><topic>Isomers</topic><topic>Macrocyclic compounds</topic><topic>Nuclear magnetic resonance</topic><topic>Structure elucidation</topic><topic>Synthesis (chemistry)</topic><topic>Terminals</topic><topic>Tetrahedrons</topic><topic>Uracil</topic><topic>Uracils</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Semenov, Vyacheslav E.</creatorcontrib><creatorcontrib>Krylova, Evgeniya S.</creatorcontrib><creatorcontrib>Galyametdinova, Irina V.</creatorcontrib><creatorcontrib>Chernova, Alla V.</creatorcontrib><creatorcontrib>Kharlamov, Sergey V.</creatorcontrib><creatorcontrib>Latypov, Shamil K.</creatorcontrib><creatorcontrib>Reznik, Vladimir S.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Semenov, Vyacheslav E.</au><au>Krylova, Evgeniya S.</au><au>Galyametdinova, Irina V.</au><au>Chernova, Alla V.</au><au>Kharlamov, Sergey V.</au><au>Latypov, Shamil K.</au><au>Reznik, Vladimir S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles</atitle><jtitle>Tetrahedron</jtitle><date>2011-09-23</date><risdate>2011</risdate><volume>67</volume><issue>38</issue><spage>7370</spage><epage>7378</epage><pages>7370-7378</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Replacement of terminal atoms of Br in 1,3-bis(bromopentyl)-5(6)-substituted uracils with 2-mercapto-5-methyl-1,3,4-thiadiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercaptoimidazole, and 2-mercaptobenzimidazoles resulted in a series of acyclic compounds and isomeric heterocyclophanes. Structures of macrocyclic regioisomers were unambiguously determined by NMR data. One of the regioisomers exhibits a hypochromic effect with respect to model compounds. The acyclic uracils obtained bridged with five-membered heterocycles are alkylated with methyliodide and methyl tosylate, and oxidated with
m-CPBA, H
2O
2, and I
2.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2011.07.034</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Tetrahedron, 2011-09, Vol.67 (38), p.7370-7378 |
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| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | Alkylation Heterocycles Heterocyclophanes Isomers Macrocyclic compounds Nuclear magnetic resonance Structure elucidation Synthesis (chemistry) Terminals Tetrahedrons Uracil Uracils |
| title | Synthesis and reactivity of acyclic and macrocyclic uracils bridged with five-membered heterocycles |
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