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Oxidative Ring Expa...
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Bergman, JanKarolinska Institute, Sweden
(författare)
Oxidative Ring Expansion of Spirocyclic Oxindole Derivatives
- Artikel/kapitelEngelska2014
Förlag, utgivningsår, omfång ...
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2014-09-16
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American Chemical Society (ACS),2014
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printrdacarrier
Nummerbeteckningar
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LIBRIS-ID:oai:DiVA.org:kth-155461
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https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-155461URI
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https://doi.org/10.1021/jo501269fDOI
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https://urn.kb.se/resolve?urn=urn:nbn:se:ri:diva-6750URI
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http://kipublications.ki.se/Default.aspx?queryparsed=id:129887710URI
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Språk:engelska
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Sammanfattning på:engelska
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Ämneskategori:ref swepub-contenttype
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Ämneskategori:art swepub-publicationtype
Anmärkningar
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QC 20141113
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Oxidation of the spirocyclic oxindole derivative, isamic acid 1, led to decarboxylation and ring expansion to quinazolino[4,5-b]quinazoline-6,8-dione 7 rather than, as previously believed, its isomer 6. The structure of 7 was confirmed by X-ray crystallography. Condensation of isatin (indole-2,3-dione) and 2-aminobenzamide led to the spirocyclic molecule, spiro[3H-indole-3,2'(1H)quinazoline]-2,4'(1H,3H)dione 8, which was also identified as an intermediate in the oxidation of isamic acid. Mild hydrolysis of 7 gave the 10-membered molecule 22. Isamic acid could easily be converted to N-nitrosoisamic acid, which when heated in ethanol underwent a ring expansion to a hydroximino derivative, 38, of compound 6. The structure of 38 was confirmed by X-ray crystallography.
Ämnesord och genrebeteckningar
Biuppslag (personer, institutioner, konferenser, titlar ...)
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Arewang, Carl-JohanAstraZeneca, Sweden
(författare)
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Svensson, Per H.RISE,KTH,Tillämpad fysikalisk kemi,SP Process Development, Sweden,Analys och fastfas(Swepub:ri)PerHSv@ri.se
(författare)
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Karolinska Institute, SwedenAstraZeneca, Sweden
(creator_code:org_t)
Sammanhörande titlar
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Ingår i:Journal of Organic Chemistry: American Chemical Society (ACS)79:19, s. 9065-90730022-32631520-6904
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