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C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
C07D209/44—Iso-indoles; Hydrogenated iso-indoles
C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
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Chemical & Material Sciences
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Organic Chemistry
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Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems
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Abstract
Phthalimidine derivs. of general formula (I) R1 = H, 1-6C alkyl/alkenyl opt. substd. by OH or SH, free or esterified or etherified, amino, COOH, halogen; aralkyl, cycloalkyl or aryl opt. substd. m, n = 0-2 m+n = 1 or 2 As tumour-inhibitors and immunosuppressants. (a) A soln. of alpha-phthalimidoglutaric acid (133 g) in AcOH (1.2 l) at 60 deg. is treated gradually with Zn dust (168 g.) and the mixt. then refluxed for 4 hrs. to give alpha-phthalmidinoglutaric acid (70%), m.p. 236-7 deg. (water). (b) this (108 g), Ac2O (833 ml) and SOCl2 (29.7 ml) are refluxed to give the anhydride (90%). m.p. 254-7 deg. dec. (c) this (2.45 g.) and urea (0.3 g) are heated at 180 deg. for 90 mins. to give 3-phthalimidinopiperidine-2,6-dione, m.p.240-2.5 deg. (AcOH).
551. β-Aroyl-α-arylmethylenepropionic acids. Part III. The isomerisation of the enol lactones of β-aroyl-α-m-methylbenzylidenepropionic acids to the corresponding 4-aryl-2-naphthoic acids, and the ultraviolet absorption spectra of their methyl esters