Facile methods for the synthesis of 5-aryl and 5-iodo pyrrolo[2,3-d] pyrimidines
An efficient and environmentally benign one-pot method has been developed for the synthesis of 4-amino-5-arylpyrrolo[2,3-d]pyrimidines. Phthalimido acetophenones were reacted with cyanoacetamide to give 2-amino-4-phenyl-1H- pyrrole-3-carboxamides, which were further converted to 5-aryl-3H-pyrrolo[2,3-d] pyrimidin-4-ones. A novel method is also developed for the synthesis of 4-amino-5-iodopyrrolo[2,3-d]pyrimidines.
Venkata Rao,Raghu Prasad,Raghuram Rao
p. E380-E383
(2014/11/07)
Synthesis of 4-Aryl-2-benzazepine-1,5-diones by Photocyclization of N-(2-Arylethyl)phthalimides
The photocyclization of N-(2-arylethyl)phthalimides to 4-aryl-2-benzazepine-1,5-diones is described.We found that the presence of electron donating substituents on the aryl ring (as in 10a and b) is necessary for the cyclization process to occur.The procedure also allowed synthesis of 2-benzazepinediones with a carboxylate group at C3 (11c and d) which were obtained as 1:1 mixture of diastereoisomers.The results of irradiating phthalimides 12, which bear an oxygenated substituent at the benzylic position, depended on the nature of the substituent.Attempts to photocyclize N-(indan-2-yl)phthalimides 16 and the electron-rich phthalimide 23 failed.
Paleo, M. Rita,Dominguez, Domingo,Castedo, Luis
p. 3627 - 3638
(2007/10/02)
Ferric Chloride-Catalyzed Acylation of Aromatic Compounds with N-Phthaloyl-α-amino Acyl Chlorides without Racemisation
Reactive aromatic compounds are acylated without racemisation to aryl 1-phthalimidoalkyl ketones 4 in good yields with N-phthaloyl-α-amino acid chlorides in the presence of catalytic amounts (1 to 5 mol-percent) of FeCl3.This new method is especially useful for the synthesis of the pharmacologically interesting alkoxyaryl 1-phthalimidoalkyl ketones 6, 8, 10, and 11, which cannot be prepared in reasonable yields in the presence of other FC catalysts such as AlCl3 or SnCl4.
Effenberger, Franz,Steegmueller, Dieter
p. 117 - 124
(2007/10/02)
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