Skeletal Wagner–Meerwein rearrangement of perhydro-3a,6;4,5-diepoxyisoindoles
An investigation of a skeletal Wagner–Meerwein rearrangement of variously substituted or quinoline-annulated 3a,6;4,5-diepoxyisoindol-1-ones is reported. Optimum reaction conditions (Ac 2O, BF 3·OEt 2, rt) were discovered for the formation of the target 4,6-epoxycyclopenta[ c]pyridines in 40–80% yie...
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| Veröffentlicht in: | Tetrahedron 2011-11, Vol.67 (47), p.9148-9163 |
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| creator | Zubkov, Fedor I. Zaytsev, Vladimir P. Nikitina, Eugeniya V. Khrustalev, Victor N. Gozun, Sergey V. Boltukhina, Ekaterina V. Varlamov, Alexey V. |
| description | An investigation of a skeletal Wagner–Meerwein rearrangement of variously substituted or quinoline-annulated 3a,6;4,5-diepoxyisoindol-1-ones is reported. Optimum reaction conditions (Ac
2O, BF
3·OEt
2, rt) were discovered for the formation of the target 4,6-epoxycyclopenta[
c]pyridines in 40–80% yields. It was shown that the direction of the sigmatropic rearrangement of 3a,6;4,5-diepoxyisoindol-1-ones depended dramatically on the carboxyl group position (
exo-/
endo-) in the oxabicyclo[2.2.1]heptane moiety. The spatial structure of previously unknown 7,9-epoxycyclopenta[4,5]pyrido[1,2-
a]quinolines derived from Wagner–Meerwein rearrangement of 2,11b-epoxyoxireno[6,7]isoindolo[2,1-
a]quinolines was established based on the X-ray analysis data. The skeletal rearrangement proceeded regio- and stereospecifically in all the cases examined due to the absence of the epimerization of the carbon atoms adjacent to the carbocation centres.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2011.09.099 |
| format | Article |
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2O, BF
3·OEt
2, rt) were discovered for the formation of the target 4,6-epoxycyclopenta[
c]pyridines in 40–80% yields. It was shown that the direction of the sigmatropic rearrangement of 3a,6;4,5-diepoxyisoindol-1-ones depended dramatically on the carboxyl group position (
exo-/
endo-) in the oxabicyclo[2.2.1]heptane moiety. The spatial structure of previously unknown 7,9-epoxycyclopenta[4,5]pyrido[1,2-
a]quinolines derived from Wagner–Meerwein rearrangement of 2,11b-epoxyoxireno[6,7]isoindolo[2,1-
a]quinolines was established based on the X-ray analysis data. The skeletal rearrangement proceeded regio- and stereospecifically in all the cases examined due to the absence of the epimerization of the carbon atoms adjacent to the carbocation centres.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2011.09.099</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>3a,6;4,5-Diepoxyisoindoles ; 4,6-Epoxycyclopenta[ c]pyridine ; 6b,9-Epoxyisoindolo[2,1- a]quinolines ; Carbon ; Carboxyl group ; Formations ; Intramolecular Diels–Alder reaction of furan (IMDAF) ; Optimization ; Tetrahedrons ; Wagner–Meerwein rearrangement ; X-rays</subject><ispartof>Tetrahedron, 2011-11, Vol.67 (47), p.9148-9163</ispartof><rights>2011 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c330t-20d732d09e527842b84ac0da858fdacc0f91493446008ece881aa1f365a5f8c63</citedby><cites>FETCH-LOGICAL-c330t-20d732d09e527842b84ac0da858fdacc0f91493446008ece881aa1f365a5f8c63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402011014694$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Zubkov, Fedor I.</creatorcontrib><creatorcontrib>Zaytsev, Vladimir P.</creatorcontrib><creatorcontrib>Nikitina, Eugeniya V.</creatorcontrib><creatorcontrib>Khrustalev, Victor N.</creatorcontrib><creatorcontrib>Gozun, Sergey V.</creatorcontrib><creatorcontrib>Boltukhina, Ekaterina V.</creatorcontrib><creatorcontrib>Varlamov, Alexey V.</creatorcontrib><title>Skeletal Wagner–Meerwein rearrangement of perhydro-3a,6;4,5-diepoxyisoindoles</title><title>Tetrahedron</title><description>An investigation of a skeletal Wagner–Meerwein rearrangement of variously substituted or quinoline-annulated 3a,6;4,5-diepoxyisoindol-1-ones is reported. Optimum reaction conditions (Ac
2O, BF
3·OEt
2, rt) were discovered for the formation of the target 4,6-epoxycyclopenta[
c]pyridines in 40–80% yields. It was shown that the direction of the sigmatropic rearrangement of 3a,6;4,5-diepoxyisoindol-1-ones depended dramatically on the carboxyl group position (
exo-/
endo-) in the oxabicyclo[2.2.1]heptane moiety. The spatial structure of previously unknown 7,9-epoxycyclopenta[4,5]pyrido[1,2-
a]quinolines derived from Wagner–Meerwein rearrangement of 2,11b-epoxyoxireno[6,7]isoindolo[2,1-
a]quinolines was established based on the X-ray analysis data. The skeletal rearrangement proceeded regio- and stereospecifically in all the cases examined due to the absence of the epimerization of the carbon atoms adjacent to the carbocation centres.
[Display omitted]</description><subject>3a,6;4,5-Diepoxyisoindoles</subject><subject>4,6-Epoxycyclopenta[ c]pyridine</subject><subject>6b,9-Epoxyisoindolo[2,1- a]quinolines</subject><subject>Carbon</subject><subject>Carboxyl group</subject><subject>Formations</subject><subject>Intramolecular Diels–Alder reaction of furan (IMDAF)</subject><subject>Optimization</subject><subject>Tetrahedrons</subject><subject>Wagner–Meerwein rearrangement</subject><subject>X-rays</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKAzEUhoMoWKsP4G6WLjrjyWVudCXFG1S6UHEZYnKmpk4nNZmq3fkOvqFPYkpdCz-czf_9cD5CTilkFGhxvsh67DMGlGZQx9R7ZEBFIdJc0GKfDAAEpAIYHJKjEBYAscn4gMzuX7HFXrXJk5p36H--vu8Q_QfaLvGovFfdHJfY9YlrkhX6l43xLuVqVIzFKE-NxZX73NjgbGdci-GYHDSqDXjyd4fk8eryYXKTTmfXt5OLaao5hz5lYErODNSYs7IS7LkSSoNRVV41RmkNTU1FzYUoACrUWFVUKdrwIld5U-mCD8nZbnfl3dsaQy-XNmhsW9WhWwdJy8iWBQMWq3RX1d6F4LGRK2-Xym8kBbmVJxcyypNbeRLqmDoy4x2D8Yd3i14GbbHTaKxH3Uvj7D_0L-0OeC0</recordid><startdate>20111125</startdate><enddate>20111125</enddate><creator>Zubkov, Fedor I.</creator><creator>Zaytsev, Vladimir P.</creator><creator>Nikitina, Eugeniya V.</creator><creator>Khrustalev, Victor N.</creator><creator>Gozun, Sergey V.</creator><creator>Boltukhina, Ekaterina V.</creator><creator>Varlamov, Alexey V.</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>20111125</creationdate><title>Skeletal Wagner–Meerwein rearrangement of perhydro-3a,6;4,5-diepoxyisoindoles</title><author>Zubkov, Fedor I. ; Zaytsev, Vladimir P. ; Nikitina, Eugeniya V. ; Khrustalev, Victor N. ; Gozun, Sergey V. ; Boltukhina, Ekaterina V. ; Varlamov, Alexey V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-20d732d09e527842b84ac0da858fdacc0f91493446008ece881aa1f365a5f8c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>3a,6;4,5-Diepoxyisoindoles</topic><topic>4,6-Epoxycyclopenta[ c]pyridine</topic><topic>6b,9-Epoxyisoindolo[2,1- a]quinolines</topic><topic>Carbon</topic><topic>Carboxyl group</topic><topic>Formations</topic><topic>Intramolecular Diels–Alder reaction of furan (IMDAF)</topic><topic>Optimization</topic><topic>Tetrahedrons</topic><topic>Wagner–Meerwein rearrangement</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zubkov, Fedor I.</creatorcontrib><creatorcontrib>Zaytsev, Vladimir P.</creatorcontrib><creatorcontrib>Nikitina, Eugeniya V.</creatorcontrib><creatorcontrib>Khrustalev, Victor N.</creatorcontrib><creatorcontrib>Gozun, Sergey V.</creatorcontrib><creatorcontrib>Boltukhina, Ekaterina V.</creatorcontrib><creatorcontrib>Varlamov, Alexey V.</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>Zubkov, Fedor I.</au><au>Zaytsev, Vladimir P.</au><au>Nikitina, Eugeniya V.</au><au>Khrustalev, Victor N.</au><au>Gozun, Sergey V.</au><au>Boltukhina, Ekaterina V.</au><au>Varlamov, Alexey V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Skeletal Wagner–Meerwein rearrangement of perhydro-3a,6;4,5-diepoxyisoindoles</atitle><jtitle>Tetrahedron</jtitle><date>2011-11-25</date><risdate>2011</risdate><volume>67</volume><issue>47</issue><spage>9148</spage><epage>9163</epage><pages>9148-9163</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>An investigation of a skeletal Wagner–Meerwein rearrangement of variously substituted or quinoline-annulated 3a,6;4,5-diepoxyisoindol-1-ones is reported. Optimum reaction conditions (Ac
2O, BF
3·OEt
2, rt) were discovered for the formation of the target 4,6-epoxycyclopenta[
c]pyridines in 40–80% yields. It was shown that the direction of the sigmatropic rearrangement of 3a,6;4,5-diepoxyisoindol-1-ones depended dramatically on the carboxyl group position (
exo-/
endo-) in the oxabicyclo[2.2.1]heptane moiety. The spatial structure of previously unknown 7,9-epoxycyclopenta[4,5]pyrido[1,2-
a]quinolines derived from Wagner–Meerwein rearrangement of 2,11b-epoxyoxireno[6,7]isoindolo[2,1-
a]quinolines was established based on the X-ray analysis data. The skeletal rearrangement proceeded regio- and stereospecifically in all the cases examined due to the absence of the epimerization of the carbon atoms adjacent to the carbocation centres.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2011.09.099</doi><tpages>16</tpages></addata></record> |
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| subjects | 3a,6 4,5-Diepoxyisoindoles 4,6-Epoxycyclopenta[ c]pyridine 6b,9-Epoxyisoindolo[2,1- a]quinolines Carbon Carboxyl group Formations Intramolecular Diels–Alder reaction of furan (IMDAF) Optimization Tetrahedrons Wagner–Meerwein rearrangement X-rays |
| title | Skeletal Wagner–Meerwein rearrangement of perhydro-3a,6;4,5-diepoxyisoindoles |
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