Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis
The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles....
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| Veröffentlicht in: | Organic letters 2008-06, Vol.10 (12), p.2589-2591 |
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| container_issue | 12 |
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| container_title | Organic letters |
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| creator | Marsden, Stephen P McGonagle, Alison E McKeever-Abbas, Ben |
| description | The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy. |
| doi_str_mv | 10.1021/ol800921n |
| format | Article |
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The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. 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Lett</addtitle><description>The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.</description><subject>Aza Compounds - chemistry</subject><subject>Benzoxazoles - chemical synthesis</subject><subject>Benzoxazoles - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Molecular Structure</subject><subject>Spectrophotometry, Infrared</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9LwzAUB_AgipvTg_-A9KLgofrStE1yEaT4CwYeVDyW1zTTjLaZSXro_no7NubFUx7hw5f3voScU7ihkNBb2wgAmdDugExplrCYQ5Yc7uccJuTE-yUAHX_kMZlQkQpJOZuSuwIDNkMwKsI1xp8mBPMVFYNqzBqDsZ2PFtZFzzpoZ9HZFjf0bejCt_bGn5KjBTZen-3eGfl4fHgvnuP569NLcT-PkVEWYpnKLOWIMqdCCwTGAaVSFTDFa1Uh8DrTIpW0llVVaYlVmgvAcXORgRDAZuRqm7ty9qfXPpSt8Uo3DXba9r7kNM8lS_IRXm-hctZ7pxflypkW3VBSKDdllfuyRnuxC-2rVtd_ctfOCC63AJUvl7Z33XjjP0G_xzdwSw</recordid><startdate>20080619</startdate><enddate>20080619</enddate><creator>Marsden, Stephen P</creator><creator>McGonagle, Alison E</creator><creator>McKeever-Abbas, Ben</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080619</creationdate><title>Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis</title><author>Marsden, Stephen P ; McGonagle, Alison E ; McKeever-Abbas, Ben</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-949547aa9618e8a0370a9ccb03c7dcba07d5e8491d9bbbe9ab4680a0608508803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Aza Compounds - chemistry</topic><topic>Benzoxazoles - chemical synthesis</topic><topic>Benzoxazoles - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Molecular Structure</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Marsden, Stephen P</creatorcontrib><creatorcontrib>McGonagle, Alison E</creatorcontrib><creatorcontrib>McKeever-Abbas, Ben</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Marsden, Stephen P</au><au>McGonagle, Alison E</au><au>McKeever-Abbas, Ben</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2008-06, Vol.10 (12), p.2589-2591 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Aza Compounds - chemistry Benzoxazoles - chemical synthesis Benzoxazoles - chemistry Catalysis Cyclization Molecular Structure Spectrophotometry, Infrared |
| title | Catalytic aza-Wittig Cyclizations for Heteroaromatic Synthesis |
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