Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-][1,3]oxazine-pyrroles and related products
1,4-Dipolar cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1 H -pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxyla...
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| creator | Galeev, Andrew R Moroz, Anna A Dmitriev, Maksim V Maslivets, Andrey N |
| description | 1,4-Dipolar cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1
H
-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-
b
][1,3]oxazine-2,3′-pyrroles] as diastereomeric mixtures which exist in rapid equilibrium in solution. It was established that this phenomenon of rapid epimerization is a characteristic of other similar spiropyrido[2,1-
b
][1,3]oxazines and even related spiroquinolizines, which was demonstrated by the investigation of related products of previously reported, and reproduced in this work, 1,4-dipolar cycloaddition reactions.
Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-
b
][1,3]oxazine-pyrroles and repetition of syntheses from the literature. |
| doi_str_mv | 10.1039/d1ra08384h |
| format | Article |
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H
-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-
b
][1,3]oxazine-2,3′-pyrroles] as diastereomeric mixtures which exist in rapid equilibrium in solution. It was established that this phenomenon of rapid epimerization is a characteristic of other similar spiropyrido[2,1-
b
][1,3]oxazines and even related spiroquinolizines, which was demonstrated by the investigation of related products of previously reported, and reproduced in this work, 1,4-dipolar cycloaddition reactions.
Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-
b
][1,3]oxazine-pyrroles and repetition of syntheses from the literature.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d1ra08384h</identifier><identifier>PMID: 35424489</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemistry ; Cyclic compounds ; Cycloaddition ; Diketones ; Dipoles ; Pyrroles ; Synthesis</subject><ispartof>RSC advances, 2021-12, Vol.12 (1), p.578-587</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2022</rights><rights>This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c395t-d773478092838ef3843bc0b6b0ec5c7feeb40f4d602090f984a0e26c2d5201383</citedby><cites>FETCH-LOGICAL-c395t-d773478092838ef3843bc0b6b0ec5c7feeb40f4d602090f984a0e26c2d5201383</cites><orcidid>0000-0003-3951-7691 ; 0000-0002-8887-7899 ; 0000-0002-8817-0543</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694240/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8694240/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35424489$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Galeev, Andrew R</creatorcontrib><creatorcontrib>Moroz, Anna A</creatorcontrib><creatorcontrib>Dmitriev, Maksim V</creatorcontrib><creatorcontrib>Maslivets, Andrey N</creatorcontrib><title>Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-][1,3]oxazine-pyrroles and related products</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>1,4-Dipolar cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1
H
-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-
b
][1,3]oxazine-2,3′-pyrroles] as diastereomeric mixtures which exist in rapid equilibrium in solution. It was established that this phenomenon of rapid epimerization is a characteristic of other similar spiropyrido[2,1-
b
][1,3]oxazines and even related spiroquinolizines, which was demonstrated by the investigation of related products of previously reported, and reproduced in this work, 1,4-dipolar cycloaddition reactions.
Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-
b
][1,3]oxazine-pyrroles and repetition of syntheses from the literature.</description><subject>Chemistry</subject><subject>Cyclic compounds</subject><subject>Cycloaddition</subject><subject>Diketones</subject><subject>Dipoles</subject><subject>Pyrroles</subject><subject>Synthesis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpVkk9r3DAQxUVJaUKaS-8NhtzKuh39sdbOoRA2abcQKJT2FIKQpXFWwWs5kh2y-z3yfaPtJttUFw2837wRb0TIBwqfKfDqi6VBQ8lLsXhDDhgImTOQ1d6rep8cxXgL6ciCMknfkX1eCCZEWR2Qx9nKtF5b6wbnu8w32Xx08Qa7jE5Ebl3vW4ynWVx1wwKji5nubBZ072yGvVticGv90tmMndnUunVrtFnsXfD9Kjjrr9iE5tdXdMKv_YNeuw7zJISN99YQWz2klj54O5ohvidvG91GPHq-D8mfbxe_Z_P88uf3H7Ozy9zwqhhyO51yMS2hYikAbFIIvDZQyxrQFGbaINYCGmElMKigqUqhAZk0zBYMKC_5Ifm69e3HeonWYDcE3ao-uKUOK-W1U_8rnVuoG3-vSlmlBCEZnDwbBH83YhzUrR9DSiCqlLTkrGRcJurTljLBxxiw2U2goDZbVOf019nfLc4TfPz6TTv0ZWcJ-LgFQjQ79d834E-6daST</recordid><startdate>20211222</startdate><enddate>20211222</enddate><creator>Galeev, Andrew R</creator><creator>Moroz, Anna A</creator><creator>Dmitriev, Maksim V</creator><creator>Maslivets, Andrey N</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-3951-7691</orcidid><orcidid>https://orcid.org/0000-0002-8887-7899</orcidid><orcidid>https://orcid.org/0000-0002-8817-0543</orcidid></search><sort><creationdate>20211222</creationdate><title>Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-][1,3]oxazine-pyrroles and related products</title><author>Galeev, Andrew R ; Moroz, Anna A ; Dmitriev, Maksim V ; Maslivets, Andrey N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c395t-d773478092838ef3843bc0b6b0ec5c7feeb40f4d602090f984a0e26c2d5201383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemistry</topic><topic>Cyclic compounds</topic><topic>Cycloaddition</topic><topic>Diketones</topic><topic>Dipoles</topic><topic>Pyrroles</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Galeev, Andrew R</creatorcontrib><creatorcontrib>Moroz, Anna A</creatorcontrib><creatorcontrib>Dmitriev, Maksim V</creatorcontrib><creatorcontrib>Maslivets, Andrey N</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Galeev, Andrew R</au><au>Moroz, Anna A</au><au>Dmitriev, Maksim V</au><au>Maslivets, Andrey N</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-][1,3]oxazine-pyrroles and related products</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2021-12-22</date><risdate>2021</risdate><volume>12</volume><issue>1</issue><spage>578</spage><epage>587</epage><pages>578-587</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>1,4-Dipolar cycloaddition has emerged as a powerful tool for the synthesis of various cyclic compounds. In the present work, 1
H
-pyrrole-2,3-diones are proposed as new dipolarophiles for 1,4-dipolar cycloaddition. Their [4 + 2] cycloaddition with dipoles generated from dimethyl acetylenedicarboxylate and pyridine was found to proceed regioselectively affording spiro[pyrido[2,1-
b
][1,3]oxazine-2,3′-pyrroles] as diastereomeric mixtures which exist in rapid equilibrium in solution. It was established that this phenomenon of rapid epimerization is a characteristic of other similar spiropyrido[2,1-
b
][1,3]oxazines and even related spiroquinolizines, which was demonstrated by the investigation of related products of previously reported, and reproduced in this work, 1,4-dipolar cycloaddition reactions.
Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-
b
][1,3]oxazine-pyrroles and repetition of syntheses from the literature.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35424489</pmid><doi>10.1039/d1ra08384h</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-3951-7691</orcidid><orcidid>https://orcid.org/0000-0002-8887-7899</orcidid><orcidid>https://orcid.org/0000-0002-8817-0543</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Chemistry Cyclic compounds Cycloaddition Diketones Dipoles Pyrroles Synthesis |
| title | Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-][1,3]oxazine-pyrroles and related products |
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