Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy
Unconjugated ynone derivatives with the 1,3-dicarbonyl structure are synthesized, and they are directly subjected to gold-catalyzed reaction with hydroxylamine without obtaining the oxime derivative. Among the different metal salts investigated, AuCl 3 is the best for yielding and obtaining two diff...
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| Veröffentlicht in: | Chemical papers 2023-12, Vol.77 (12), p.7985-7992 |
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| creator | Taşdemir, Volkan Menges, Nurettin |
| description | Unconjugated ynone derivatives with the 1,3-dicarbonyl structure are synthesized, and they are directly subjected to gold-catalyzed reaction with hydroxylamine without obtaining the oxime derivative. Among the different metal salts investigated, AuCl
3
is the best for yielding and obtaining two different heterocyclic skeletons. Thanks to this reaction, two important heterocyclic molecules, 2
H
-1,2-oxazine and 1-hydroxypyrrole, are obtained as a one-pot and single-step strategy with favorable yields. Eleven different 2
H
-1,2-oxazine and 6 different 1-hydroxypyrrole derivatives are synthesized using starting compounds containing different substituents, in which steric hindrance and electronic effect are also taken into account. When the same reaction is carried out with the unconjugated ynone derivative containing only one carbonyl group, the only 1-hydroxypyrrole derivative is observed to be formed, and 1,2-oxazine ring is not observed.
Graphical abstract |
| doi_str_mv | 10.1007/s11696-023-03041-6 |
| format | Article |
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3
is the best for yielding and obtaining two different heterocyclic skeletons. Thanks to this reaction, two important heterocyclic molecules, 2
H
-1,2-oxazine and 1-hydroxypyrrole, are obtained as a one-pot and single-step strategy with favorable yields. Eleven different 2
H
-1,2-oxazine and 6 different 1-hydroxypyrrole derivatives are synthesized using starting compounds containing different substituents, in which steric hindrance and electronic effect are also taken into account. When the same reaction is carried out with the unconjugated ynone derivative containing only one carbonyl group, the only 1-hydroxypyrrole derivative is observed to be formed, and 1,2-oxazine ring is not observed.
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3
is the best for yielding and obtaining two different heterocyclic skeletons. Thanks to this reaction, two important heterocyclic molecules, 2
H
-1,2-oxazine and 1-hydroxypyrrole, are obtained as a one-pot and single-step strategy with favorable yields. Eleven different 2
H
-1,2-oxazine and 6 different 1-hydroxypyrrole derivatives are synthesized using starting compounds containing different substituents, in which steric hindrance and electronic effect are also taken into account. When the same reaction is carried out with the unconjugated ynone derivative containing only one carbonyl group, the only 1-hydroxypyrrole derivative is observed to be formed, and 1,2-oxazine ring is not observed.
Graphical abstract</description><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Carbonyl groups</subject><subject>Carbonyls</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Gold</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>Original Paper</subject><subject>Steric hindrance</subject><issn>0366-6352</issn><issn>1336-9075</issn><issn>2585-7290</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kMFO3DAURa2qlTql_AArS2wxvGc7TrJEqAUkpG7YW57EzmSa2sF2EJkf6e_WZZDYsXqLe-590iHkDOESAeqrhKhaxYALBgIkMvWJbFAIxVqoq89kA0IppkTFv5JvKe0BpIQKNuTvbZh61plspvVge9qt3TQeTB6Dp8HRxXfB75fB5JKtPnhLexvH5wI820RdiJTfMbzgLLyYw1hi43uKbLf2Mbys8xpjmCxNv-1kc_CJ5l0My7CjZYnNIb_iafTDZFnKdqYpx_JrWL-TL85MyZ6-3RPy-PPH480de_h1e39z_cA6gW1mXbXlleDIscVatsoZcFw0ErHa1ogWTNNUnXRt3WzbHlyRIWSvlHR1o2orTsj5cXaO4WmxKet9WKIvHzUvzRYll1AofqS6GFKK1uk5jn9MXDWC_u9fH_3r4l-_-teqlMSxlArsBxvfpz9o_QNa1oo2</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Taşdemir, Volkan</creator><creator>Menges, Nurettin</creator><general>Springer International Publishing</general><general>Springer Nature B.V</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><orcidid>https://orcid.org/0000-0002-5990-6275</orcidid></search><sort><creationdate>20231201</creationdate><title>Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy</title><author>Taşdemir, Volkan ; Menges, Nurettin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-c5b2532121917496fa0f2384115b711e0a885c4f978b9d0f07534d664f7867e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Carbonyl groups</topic><topic>Carbonyls</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Gold</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>Original Paper</topic><topic>Steric hindrance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Taşdemir, Volkan</creatorcontrib><creatorcontrib>Menges, Nurettin</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>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Taşdemir, Volkan</au><au>Menges, Nurettin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2023-12-01</date><risdate>2023</risdate><volume>77</volume><issue>12</issue><spage>7985</spage><epage>7992</epage><pages>7985-7992</pages><issn>0366-6352</issn><eissn>1336-9075</eissn><eissn>2585-7290</eissn><abstract>Unconjugated ynone derivatives with the 1,3-dicarbonyl structure are synthesized, and they are directly subjected to gold-catalyzed reaction with hydroxylamine without obtaining the oxime derivative. Among the different metal salts investigated, AuCl
3
is the best for yielding and obtaining two different heterocyclic skeletons. Thanks to this reaction, two important heterocyclic molecules, 2
H
-1,2-oxazine and 1-hydroxypyrrole, are obtained as a one-pot and single-step strategy with favorable yields. Eleven different 2
H
-1,2-oxazine and 6 different 1-hydroxypyrrole derivatives are synthesized using starting compounds containing different substituents, in which steric hindrance and electronic effect are also taken into account. When the same reaction is carried out with the unconjugated ynone derivative containing only one carbonyl group, the only 1-hydroxypyrrole derivative is observed to be formed, and 1,2-oxazine ring is not observed.
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| subjects | Biochemistry Biotechnology Carbonyl groups Carbonyls Chemistry Chemistry and Materials Science Chemistry/Food Science Gold Industrial Chemistry/Chemical Engineering Materials Science Medicinal Chemistry Original Paper Steric hindrance |
| title | Gold-catalyzed cyclization of unconjugated ynone derivatives for 2H-1,2-oxazine and 1-hydroxypyrrole skeletons through one-pot and single-step strategy |
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