A New Synthesis of 2-Methyleneaziridines
A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competiti...
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| Veröffentlicht in: | Journal of organic chemistry 1997-04, Vol.62 (8), p.2448-2452 |
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| container_title | Journal of organic chemistry |
| container_volume | 62 |
| creator | De Kimpe, Norbert De Smaele, Dirk Sakonyi, Zsolt |
| description | A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents. |
| doi_str_mv | 10.1021/jo962351v |
| format | Article |
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Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo962351v</identifier><identifier>PMID: 11671580</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 1997-04, Vol.62 (8), p.2448-2452</ispartof><rights>Copyright © 1997 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a351t-24cee31e5b11698cb5f7a63268d062a5702e3035d10eb310957ce53683204de83</citedby><cites>FETCH-LOGICAL-a351t-24cee31e5b11698cb5f7a63268d062a5702e3035d10eb310957ce53683204de83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo962351v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo962351v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11671580$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>De Kimpe, Norbert</creatorcontrib><creatorcontrib>De Smaele, Dirk</creatorcontrib><creatorcontrib>Sakonyi, Zsolt</creatorcontrib><title>A New Synthesis of 2-Methyleneaziridines</title><title>Journal of organic chemistry</title><addtitle>J. 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Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><recordid>eNptkD1PwzAQhi0EoqUw8AdQF6QyBM527CRjqfiSykdpWVgsJ7moKWlS7AQovx6jVGXhlhvu0fueHkKOKZxTYPRiUUWScUE_dkiXCgaejMDfJV0AxjzOJO-QA2sX4EYIsU86lMqAihC6ZDDsP-Bnf7ou6zna3ParrM-8e6zn6wJL1N-5ydO8RHtI9jJdWDza7B55ub6ajW698ePN3Wg49rR7oPaYnyByiiJ2HVGYxCILtHQ_hClIpkUADDlwkVLAmFOIRJCg4DLkDPwUQ94jgzZ3Zar3Bm2tlrlNsCh0iVVjFQ1FxCWLfO7QsxZNTGWtwUytTL7UZq0oqF8xaivGsSeb2CZeYvpHbkw4wGuB3Nb4tb1r86ZkwAOhZk9TdTl5nsz810iNHX_a8jqxrqcxpbPyT_EPhY92BQ</recordid><startdate>19970418</startdate><enddate>19970418</enddate><creator>De Kimpe, Norbert</creator><creator>De Smaele, Dirk</creator><creator>Sakonyi, Zsolt</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19970418</creationdate><title>A New Synthesis of 2-Methyleneaziridines</title><author>De Kimpe, Norbert ; De Smaele, Dirk ; Sakonyi, Zsolt</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a351t-24cee31e5b11698cb5f7a63268d062a5702e3035d10eb310957ce53683204de83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>De Kimpe, Norbert</creatorcontrib><creatorcontrib>De Smaele, Dirk</creatorcontrib><creatorcontrib>Sakonyi, Zsolt</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>De Kimpe, Norbert</au><au>De Smaele, Dirk</au><au>Sakonyi, Zsolt</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New Synthesis of 2-Methyleneaziridines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1997-04-18</date><risdate>1997</risdate><volume>62</volume><issue>8</issue><spage>2448</spage><epage>2452</epage><pages>2448-2452</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A new synthetic route leading to 2-methyleneaziridines has been developed by base-induced 1,2-dehydrobromination of 2-(bromomethyl)aziridines. Several base-solvent pairs did not lead to 2-methyleneaziridines. Only potassium tert-butoxide in tetrahydrofuran afforded 2-methyleneaziridines in competition with the substitution products, i.e. 2-(tert-butoxymethyl)aziridines. Various attempted functionalizations of 1-(arylmethyl)-2-methyleneaziridines failed, but they proved to be excellent substrates for the synthesis of β-lactam derivatives, i.e. 1-(arylmethyl)-2-iminoazetidines, through ring expansion with azides carrying electron-withdrawing substituents.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11671580</pmid><doi>10.1021/jo962351v</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 1997-04, Vol.62 (8), p.2448-2452 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society Journals |
| title | A New Synthesis of 2-Methyleneaziridines |
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