NISCAIR Online Periodicals Repository Community: Indian Journal of Chemistry -Section B (IJC-B)

Synthesis of a novel water soluble phthalimide derivative of acetaminophen as potential analgesic and antipyretic agent

Title: Synthesis of a novel water soluble phthalimide derivative of acetaminophen as potential analgesic and antipyretic agent

Authors: Reddy, Y Dathu; Kumari, Y Bharathi; Dubey, P K

Abstract: A short process for the preparation of water soluble, potential analgesic compound, N-[(4-hydroxy-phenylcarbamoyl)-methyl]-phthalamic acid 4 has been developed. Two synthetic routes (A and B) have been established for the preparation of 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-(4-hydroxyphenyl)acetamide 3. In route A, 4-aminophenol 5 is reacted with chloroacetyl chloride 6 in solution of potassium acetate and acetic acid at 0-5°C to yield N-(4-hydroxyphenyl)-2-chloroacetamide 7. The latter is reacted with potassium phthalimide 8 and KI in DMF at 130°C to give 3. Alternatively, in route B, reaction of phthalic anhydride 8 with glycine 9 at 150°C yields the acid intermediate (1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid 11, which on reaction with 4-aminophenol 6 in DMF and in the presence of dicyclohexylcarbodimide gives 3. The latter is hydrolysed in ethanolic KOH to afford 4.

Page(s): 691-693

Studies on reactions of anhydrides with Schiff bases

Title: Studies on reactions of anhydrides with Schiff bases

Authors: Kumar, Padam Praveen; Mohiuddin, S M G; Devi, B Rama; Dubey, P K

Abstract: Reaction of phthalic anhydride 1 with benzylidineanilines 2, in equimolar ratio in hot acetic acid, yields N-arylphthalimides 3. Compound 1 reacts with the arylimine part of the Schiff base eliminating benzaldehyde part 4 as the bye-product. This reaction of 1 with 2 is also found to occur with other anhydrides like succinic anhydride 5, maleic anhydride 7 and acetic anhydride 9 resulting in the formation of the corresponding N-arylimides, namely, succinicimide 6, maleicimide 8 and aceticimide 10 respectively. In all the above reactions, the by-product, i.e. benzaldehyde or p-chlorobenzaldehyde can be isolated and characterized as its 2,4-dinitrophenylhydrazone derivative. Probable mechanism for the formation of imides from the corresponding anhydrides and Schiff bases has been suggested.

Page(s): 686-690

Synthesis of some new isoxazolyldihydro[1,2,4]triazolo[1,5-b] isoxazoles and dihydroimidazo[4,5-b]indolylisoxazoles as possible biodynamic agents

Title: Synthesis of some new isoxazolyldihydro[1,2,4]triazolo[1,5-b] isoxazoles and dihydroimidazo[4,5-b]indolylisoxazoles as possible biodynamic agents

Authors: Rajanarendar, E; Venkateshwarlu, P; Ramakrishna, S

Abstract: Synthesis of new isoxazolyl[1,2,4]triazolo[1,5-b]isoxazoles and imidazo[4,5-b]indolyl isoxazoles have been achieved by interaction of isoxazole Schiff base with isoxazole amines and isatin respectively.

Page(s): 677-685

Antimicrobial evaluation of some novel isoxazoles, cyanopyridines and pyrimidinthiones

Title: Antimicrobial evaluation of some novel isoxazoles, cyanopyridines and pyrimidinthiones

Authors: Solankee, Anjani; Patel, Kirti; Patel, Rajnikant

Abstract: The title compounds 7a-f, 8a-f and 9a-f have been prepared from chalcones 6a-f having s-triazine nucleus. These chalcones on cyclisation with hydroxyl amine hydrochloride in the presence of alkali and malononitrile in the presence of ammonium acetate give isoxazoles 7a-f and cyanopyridines 8a-f respectively. Chalcones 6a-f on condensation with thiourea in the presence of alkali give pyrimidinthiones 9a-f. Structures of newly synthesised compound have been established on the basis of their elemental analysis, IR and ¹H NMR spectral data. All the synthesised compounds have been screened for their antimicrobial activity.

Page(s): 671-676