Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis
Benzylidene imidazolones with ortho‐ secondary aminogroup undergo acid‐promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids p...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2022-04, Vol.364 (9), p.1587-1595 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Ivanov, Dmitrii S. Zaitseva, Elvira R. Smirnov, Alexander Yu Rustamova, Dina A. Mikhaylov, Andrey A. Sycheva, Maria A. Gluschenko, Darya A. Baleeva, Nadezhda S. Baranov, Mikhail S. |
| description | Benzylidene imidazolones with ortho‐ secondary aminogroup undergo acid‐promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. Each of the processes proceeds with exclusive atom‐economy. |
| doi_str_mv | 10.1002/adsc.202200109 |
| format | Article |
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Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. 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Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. Each of the processes proceeds with exclusive atom‐economy.</description><subject>[1,5]-hydride shift</subject><subject>Acids</subject><subject>Heterocyclic compounds</subject><subject>intramolecular hydroamination</subject><subject>Lewis acid</subject><subject>spiroindolines</subject><subject>spirotetrahydroquinolines</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAQxyMEEqWwMltiTrGd5sNsIXxVqsRQYLUc-wyukrjYKVU68Qg8DjtvwpOQqqiMLHc3_P53ul8QnBI8IhjTc6G8HFFMKcYEs71gQBISh2OSsP3dHOPD4Mj7eY-kWZoOAle8QG2VeQP3DE2LZgvjrOxkZdaiNbZBViP6_f4xA9nXvDaNLaFZm8ooaABNaqPE2la2AX-BprAyHj2B80uPLt3XZ-NbUCiXRnlUiFZUnTf-ODjQovJw8tuHwePN9UNxF07vbydFPg1lRFIWSqy0BC1oBKDLJM4SpiGlJEqFyBhOCIv7V1nJsogJqjGhio1ZomJapmNBIRoGZ9u9C2dfl-BbPrdL1_QnOU3iGMcsorinRltKOuu9A80XztTCdZxgvvHKN175zmsfYNvAylTQ_UPz_GpW_GV_AB5WgEw</recordid><startdate>20220426</startdate><enddate>20220426</enddate><creator>Ivanov, Dmitrii S.</creator><creator>Zaitseva, Elvira R.</creator><creator>Smirnov, Alexander Yu</creator><creator>Rustamova, Dina A.</creator><creator>Mikhaylov, Andrey A.</creator><creator>Sycheva, Maria A.</creator><creator>Gluschenko, Darya A.</creator><creator>Baleeva, Nadezhda S.</creator><creator>Baranov, Mikhail S.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-9339-7603</orcidid><orcidid>https://orcid.org/0000-0001-9433-9141</orcidid></search><sort><creationdate>20220426</creationdate><title>Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis</title><author>Ivanov, Dmitrii S. ; Zaitseva, Elvira R. ; Smirnov, Alexander Yu ; Rustamova, Dina A. ; Mikhaylov, Andrey A. ; Sycheva, Maria A. ; Gluschenko, Darya A. ; Baleeva, Nadezhda S. ; Baranov, Mikhail S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3179-c0dfcefa23eefb65869fe72137aa89061952209b9839a2f012d9496d52b74a2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>[1,5]-hydride shift</topic><topic>Acids</topic><topic>Heterocyclic compounds</topic><topic>intramolecular hydroamination</topic><topic>Lewis acid</topic><topic>spiroindolines</topic><topic>spirotetrahydroquinolines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ivanov, Dmitrii S.</creatorcontrib><creatorcontrib>Zaitseva, Elvira R.</creatorcontrib><creatorcontrib>Smirnov, Alexander Yu</creatorcontrib><creatorcontrib>Rustamova, Dina A.</creatorcontrib><creatorcontrib>Mikhaylov, Andrey A.</creatorcontrib><creatorcontrib>Sycheva, Maria A.</creatorcontrib><creatorcontrib>Gluschenko, Darya A.</creatorcontrib><creatorcontrib>Baleeva, Nadezhda S.</creatorcontrib><creatorcontrib>Baranov, Mikhail S.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ivanov, Dmitrii S.</au><au>Zaitseva, Elvira R.</au><au>Smirnov, Alexander Yu</au><au>Rustamova, Dina A.</au><au>Mikhaylov, Andrey A.</au><au>Sycheva, Maria A.</au><au>Gluschenko, Darya A.</au><au>Baleeva, Nadezhda S.</au><au>Baranov, Mikhail S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2022-04-26</date><risdate>2022</risdate><volume>364</volume><issue>9</issue><spage>1587</spage><epage>1595</epage><pages>1587-1595</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Benzylidene imidazolones with ortho‐ secondary aminogroup undergo acid‐promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. Each of the processes proceeds with exclusive atom‐economy.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202200109</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-9339-7603</orcidid><orcidid>https://orcid.org/0000-0001-9433-9141</orcidid></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | [1,5]-hydride shift Acids Heterocyclic compounds intramolecular hydroamination Lewis acid spiroindolines spirotetrahydroquinolines |
| title | Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis |
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