Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones
1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl 2 ) and water. The reaction proceeded via the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2 Н -pyrrole intermediates, the latter of which was transformed b...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-07, Vol.56 (7), p.881-887 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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| creator | Rostovskii, Nikolai V. Smetanin, Ilia A. Koronatov, Alexander N. Agafonova, Anastasiya V. Potapenkov, Vasilii V. Khlebnikov, Alexander F. Novikov, Mikhail S. |
| description | 1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl
2
) and water. The reaction proceeded
via
the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2
Н
-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2
Н
-pyrrole intermediate. |
| doi_str_mv | 10.1007/s10593-020-02745-x |
| format | Article |
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2
) and water. The reaction proceeded
via
the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2
Н
-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2
Н
-pyrrole intermediate.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-020-02745-x</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Bromination ; Carbonyls ; Chemistry ; Chemistry and Materials Science ; Dienes ; Isomerization ; Organic Chemistry ; Pharmacy ; Silica gel ; Silicon dioxide ; Zinc chloride</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-07, Vol.56 (7), p.881-887</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020</rights><rights>COPYRIGHT 2020 Springer</rights><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-810507fd8b83b3c6a68581e1e1ecc5b22b7a1d4fa9006298798f8269cf89df503</citedby><cites>FETCH-LOGICAL-c358t-810507fd8b83b3c6a68581e1e1ecc5b22b7a1d4fa9006298798f8269cf89df503</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10593-020-02745-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10593-020-02745-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Rostovskii, Nikolai V.</creatorcontrib><creatorcontrib>Smetanin, Ilia A.</creatorcontrib><creatorcontrib>Koronatov, Alexander N.</creatorcontrib><creatorcontrib>Agafonova, Anastasiya V.</creatorcontrib><creatorcontrib>Potapenkov, Vasilii V.</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F.</creatorcontrib><creatorcontrib>Novikov, Mikhail S.</creatorcontrib><title>Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl
2
) and water. The reaction proceeded
via
the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2
Н
-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2
Н
-pyrrole intermediate.</description><subject>Bromination</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Dienes</subject><subject>Isomerization</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Silica gel</subject><subject>Silicon dioxide</subject><subject>Zinc chloride</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhYMoWKt_wNWAW1PznCTLUnxBQRe6DplMUqZMJzWZgU5_vakjuJPL5ZLL-W4OB4BbjBYYIfGQMOKKQkRQbsE4PJyBGeaCQkk5PQczhJCCFBNyCa5S2uanwJLNwPvSNjW0pjfteHR1EZ2J0XQbt3NdXwRfYGjs2EICzdFUQ28gvqewblznUtGHgsH9GGNomy5LQl5egwtv2uRufuccfD49fqxe4Prt-XW1XENLueyhzIaR8LWsJK2oLU0pucTuVNbyipBKGFwzbxRCJVFSKOklKZX1UtWeIzoHd9PdfQxfg0u93oYhdvlLTRhVlLGSkKxaTKqNaZ1uOh_6aGyu2u0am_36Ju-XJWWECiFZBsgE2BhSis7rfWx2Jo4aI32KWk9R6xy1_olaHzJEJyhlcc4u_nn5h_oGokZ_Vg</recordid><startdate>20200701</startdate><enddate>20200701</enddate><creator>Rostovskii, Nikolai V.</creator><creator>Smetanin, Ilia A.</creator><creator>Koronatov, Alexander N.</creator><creator>Agafonova, Anastasiya V.</creator><creator>Potapenkov, Vasilii V.</creator><creator>Khlebnikov, Alexander F.</creator><creator>Novikov, Mikhail S.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20200701</creationdate><title>Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones</title><author>Rostovskii, Nikolai V. ; Smetanin, Ilia A. ; Koronatov, Alexander N. ; Agafonova, Anastasiya V. ; Potapenkov, Vasilii V. ; Khlebnikov, Alexander F. ; Novikov, Mikhail S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-810507fd8b83b3c6a68581e1e1ecc5b22b7a1d4fa9006298798f8269cf89df503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Bromination</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Dienes</topic><topic>Isomerization</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Silica gel</topic><topic>Silicon dioxide</topic><topic>Zinc chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rostovskii, Nikolai V.</creatorcontrib><creatorcontrib>Smetanin, Ilia A.</creatorcontrib><creatorcontrib>Koronatov, Alexander N.</creatorcontrib><creatorcontrib>Agafonova, Anastasiya V.</creatorcontrib><creatorcontrib>Potapenkov, Vasilii V.</creatorcontrib><creatorcontrib>Khlebnikov, Alexander F.</creatorcontrib><creatorcontrib>Novikov, Mikhail S.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rostovskii, Nikolai V.</au><au>Smetanin, Ilia A.</au><au>Koronatov, Alexander N.</au><au>Agafonova, Anastasiya V.</au><au>Potapenkov, Vasilii V.</au><au>Khlebnikov, Alexander F.</au><au>Novikov, Mikhail S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2020-07-01</date><risdate>2020</risdate><volume>56</volume><issue>7</issue><spage>881</spage><epage>887</epage><pages>881-887</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl
2
) and water. The reaction proceeded
via
the formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2
Н
-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2
Н
-pyrrole intermediate.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-020-02745-x</doi><tpages>7</tpages></addata></record> |
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| subjects | Bromination Carbonyls Chemistry Chemistry and Materials Science Dienes Isomerization Organic Chemistry Pharmacy Silica gel Silicon dioxide Zinc chloride |
| title | Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones |
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