Oxidative Ring Expansion of Spirocyclic Oxindole Derivatives

Sökning: L773:0022 3263 > Oxidative Ring Expa...

QC 20141113
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.

Arewang, Carl-JohanAstraZeneca, Sweden (författare)
Svensson, Per H.RISE,KTH,Tillämpad fysikalisk kemi,SP Process Development, Sweden,Analys och fastfas(Swepub:ri)PerHSv@ri.se (författare)
Karolinska Institute, SwedenAstraZeneca, Sweden (creator_code:org_t)

Ingår i:Journal of Organic Chemistry: American Chemical Society (ACS)79:19, s. 9065-90730022-32631520-6904

Av författaren/redakt...: Bergman, Jan; Arewang, Carl-Jo ...; Svensson, Per H.

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