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Oxidative Ring Expa...
Oxidative Ring Expansion of Spirocyclic Oxindole Derivatives
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- Bergman, Jan (author)
- Karolinska Institute, Sweden
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- Arewang, Carl-Johan (author)
- AstraZeneca, Sweden
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- Svensson, Per H. (author)
- RISE,KTH,Tillämpad fysikalisk kemi,SP Process Development, Sweden,Analys och fastfas
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(creator_code:org_t)
- 2014-09-16
- 2014
- English.
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 79:19, s. 9065-9073
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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