(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans
Lewis base dependent (3 + 3) annulation of δ-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole is reported. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with δ-acetoxy allenoates via 6- exo-dig cyclisation at room te...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-06, Vol.21 (24), p.521-532 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Debnath, Shubham Chauhan, Sachin Kumara Swamy, K. C |
| description | Lewis base dependent (3 + 3) annulation of δ-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole is reported. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with δ-acetoxy allenoates
via
6-
exo-dig
cyclisation at room temperature (25 °C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between
N
-Boc-oxindole and δ-acetoxy allenoates goes through 6-
endo-dig
cyclisation, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
Lewis base-controlled (3 + 3) annulation of δ-acetoxy allenoates with
N
-Boc-oxindole, benzofuranone, or pyrazolone affords fused pyrans; the base DBU gives pyrans, while DMAP affords dihydropyrans. |
| doi_str_mv | 10.1039/d3ob00597f |
| format | Article |
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via
6-
exo-dig
cyclisation at room temperature (25 °C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between
N
-Boc-oxindole and δ-acetoxy allenoates goes through 6-
endo-dig
cyclisation, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
Lewis base-controlled (3 + 3) annulation of δ-acetoxy allenoates with
N
-Boc-oxindole, benzofuranone, or pyrazolone affords fused pyrans; the base DBU gives pyrans, while DMAP affords dihydropyrans.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob00597f</identifier><identifier>PMID: 37260347</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carbonyl compounds ; Carbonyls ; Chemical reactions ; Lewis base ; Organic chemistry ; Pyrazolones ; Room temperature ; Substrates</subject><ispartof>Organic & biomolecular chemistry, 2023-06, Vol.21 (24), p.521-532</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-af367271585f1aa246fb3e4b5a5b0d294894cdd9cd300bd91b814540d2ef461f3</citedby><cites>FETCH-LOGICAL-c337t-af367271585f1aa246fb3e4b5a5b0d294894cdd9cd300bd91b814540d2ef461f3</cites><orcidid>0000-0002-7617-706X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37260347$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Debnath, Shubham</creatorcontrib><creatorcontrib>Chauhan, Sachin</creatorcontrib><creatorcontrib>Kumara Swamy, K. C</creatorcontrib><title>(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Lewis base dependent (3 + 3) annulation of δ-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole is reported. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with δ-acetoxy allenoates
via
6-
exo-dig
cyclisation at room temperature (25 °C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between
N
-Boc-oxindole and δ-acetoxy allenoates goes through 6-
endo-dig
cyclisation, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
Lewis base-controlled (3 + 3) annulation of δ-acetoxy allenoates with
N
-Boc-oxindole, benzofuranone, or pyrazolone affords fused pyrans; the base DBU gives pyrans, while DMAP affords dihydropyrans.</description><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Chemical reactions</subject><subject>Lewis base</subject><subject>Organic chemistry</subject><subject>Pyrazolones</subject><subject>Room temperature</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0c9PwyAUB3BiNE6nF-8aEi9TM4VCSznO6dRkyS56bqCAdmEwoY32v7f74Uw88cj75OXl-wA4w-gWI8LvFPESoZQzsweOMGVsiFLC93d1gnrgOMY5QpizjB6CHmFJhghlR0ANCLyB5AqOnGusqCvvoDdQlLr23y0U1mrnRa0j_KrqD9h9bBWFtBqWIkjvWgtjI2Md1sZqoSr3DmsPTRO1gss2CBdPwIERNurT7dsHb5PH1_HzcDp7ehmPpsOSEFYPhSEZSxhO89RgIRKaGUk0lalIJVIJpzmnpVK8VAQhqTiWOaYp7Vra0Awb0geDzdxl8J-NjnWxqGKprRVO-yYWSZ7gjCKKaUcv_9G5b4Lrtlsplmec8KRT1xtVBh9j0KZYhmohQltgVKyyLx7I7H6d_aTDF9uRjVxotaO_YXfgfANCLHfdv-ORH4E6h84</recordid><startdate>20230621</startdate><enddate>20230621</enddate><creator>Debnath, Shubham</creator><creator>Chauhan, Sachin</creator><creator>Kumara Swamy, K. C</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7617-706X</orcidid></search><sort><creationdate>20230621</creationdate><title>(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans</title><author>Debnath, Shubham ; Chauhan, Sachin ; Kumara Swamy, K. C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-af367271585f1aa246fb3e4b5a5b0d294894cdd9cd300bd91b814540d2ef461f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Chemical reactions</topic><topic>Lewis base</topic><topic>Organic chemistry</topic><topic>Pyrazolones</topic><topic>Room temperature</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Debnath, Shubham</creatorcontrib><creatorcontrib>Chauhan, Sachin</creatorcontrib><creatorcontrib>Kumara Swamy, K. C</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Debnath, Shubham</au><au>Chauhan, Sachin</au><au>Kumara Swamy, K. C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-06-21</date><risdate>2023</risdate><volume>21</volume><issue>24</issue><spage>521</spage><epage>532</epage><pages>521-532</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Lewis base dependent (3 + 3) annulation of δ-acetoxy allenoates with benzofuranone, pyrazolone, and Boc-protected oxindole is reported. In the presence of catalytic DBU, oxindole, benzofuranone, and pyrazolone undergo (3 + 3) annulation with δ-acetoxy allenoates
via
6-
exo-dig
cyclisation at room temperature (25 °C) to afford fused pyran scaffolds. On the other hand, by employing catalytic DMAP, the reaction between
N
-Boc-oxindole and δ-acetoxy allenoates goes through 6-
endo-dig
cyclisation, leading to distinct dihydropyrans that contain an exocyclic double bond; similar products were also obtained by using benzofuranone and pyrazolone.
Lewis base-controlled (3 + 3) annulation of δ-acetoxy allenoates with
N
-Boc-oxindole, benzofuranone, or pyrazolone affords fused pyrans; the base DBU gives pyrans, while DMAP affords dihydropyrans.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37260347</pmid><doi>10.1039/d3ob00597f</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-7617-706X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-06, Vol.21 (24), p.521-532 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2821640414 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Carbonyl compounds Carbonyls Chemical reactions Lewis base Organic chemistry Pyrazolones Room temperature Substrates |
| title | (3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans |
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