Synthesis of Pyridine and Phenyl Succinimides by Green Pathway and Their Antimicrobial Assay
American Journal of Heterocyclic Chemistry
Volume 4, Issue 1, March 2018, Pages: 26-29
Received: Nov. 15, 2017;
Accepted: Dec. 6, 2017;
Published: Jan. 30, 2018
Views 1464 Downloads 222
Ravindra Dhivare, Faculty of Chemistry, Civil Engg Department, JSPM’s, J. S. Polytechnic, Pune, India
Prashant Chaudhari, Faculty of Chemistry, D. Y. Patil School of Engg, D. Y. Patil Technical Campus, Lohegaon, Pune, India
Shankarsing Rajput, Department of Chemistry, SVS’s Dadasaheb Rawal College, Dondaicha, India
A simple and clean green method was implemented for the preparation of different succinimide derivatives by means of the N-substituted anilines or N-substituted 2-aminopyridines with succinic anhydride with the heating in aqueous medium. The total synthesized 3a-j compounds were evaluated against antibacterial and antifungal species.
Synthesis of Pyridine and Phenyl Succinimides by Green Pathway and Their Antimicrobial Assay, American Journal of Heterocyclic Chemistry.
Vol. 4, No. 1,
2018, pp. 26-29.
Kossakowski J. and Jarocka-Wierzba M., (2003), Synthesis of new N-substituted cyclic imides with an expected anxiolytic activity. XXII. Derivatives of 1-methoxy-5-bicyclo [2. 2. 2]-oct-5-one-2, 3-dicarboximide, Polish Pharmaceutical Society, Acta Poloniae Pharmaceutica – Drug Research, 60(5), 367-374.
Sortino M., Postigo A. and Zacchino S., (2013), Effects of chirality on the antifungal potency of methylated succinimides obtained by aspergillus fumigates biotransformation comparison with racemic ones, Molecules, 18, 5669-5683.
Chen C. Y., Chang B. R., Tsai M. R., Chang M. Y. and Chang N. C., (2003), Regio-selective reduction of N-alkyl-3-sulfonyl glutarimides to d-lactams. Formal synthesis of (6)-paroxetine and (6)-tacamonine, Tetrahedron, 59, 9383-9387.
Wijnberg J. B. P. A., Shoemaker H. E. and Speckamp, (1978), A regio selective reduction of gem-disubstituted succinimides, Tetrahedron, 34(2), 179-187.
Hong S. K., Anestis D. K., Hawco N. M., Valentovic M. A., Brown P. I. and Rankin G. O., (1996), Nephrotoxicity of N-(3-bromophenyl)-2-hydroxy succinimide: Role of halogen groups in the nephrotoxic potential of N-(halophenyl)succinimides, Toxicology, 110(1-3), 17-25.
Milton J. Kornet, and Michael Crider, (1977), Potential long-acting anticonvulsants. 2. synthesis and activity of succinimides containing an alkylating group on nitrogen or at the 3 position, Journal of Medicinal Chemistry, 20(9), 1210-1213.
Hudkins R. L., DeHaven-Hudkins D. L. and Doukas P., (1997), Design of dual acting anticonvulsant-antimuscarinic succinimides and hydantoin derivatives, Bioorganic and Medicina Chemistry Letters, 7(8), 979-984.
Jolanta Obniska, Iwona Chlebek, Krzysztof Kaminski, Andrzej J. Bojarski and Grzegorz Sata, (2012), Synthesis, anticonvulsant activity and 5-HT1A/5-HT7 receptors affinity of 1-[(4-arylpiperazin-1-yl)-propyl]-succinimides, Pharmacological Reports, 64, 326-335.
Ahlam Marouf Al-Azzawi and Ahmed Saadi Hassan, , synthesis and antimicrobial activity of new succinimides bearing different heterocycles, International Journal of Research in Pharmacy and Chemistry, 4(4), 755-762.
Maximiliano Sortino, Agustina Postigo and Susana Zacchino, (2013), Effects of chirality on the antifungal potency of methylated succinimides obtained by aspergillus fumigatus biotransformations. Comparison with racemic ones, Molecules, 18, 5669-5683.
Dhivare R. S. and Rajput S. S., (2015), Synthesis and antimicrobial evaluation of some novel bis-heterocyclic chalcones from cyclic imides under microwave irradiation, Chem Sci Rev Lett., 4(15), 937-944.
J. Trujillo-Ferrara, Ivan Vazquez, Judith Espinosa, Rosa Santillan, Norberto Farfan and Herbert Hopfl, (2003), Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetyl cholinesterase, European Journal of Pharmaceutical Sciences, 18, 313-322.
Silvia Regina Tozato Prado, Valdir Cechinel-Filho, Fatima Campos-Buzzi, Rogerio Correa, Silvia Maria Correia Suter Cadena, and Maria Benigna Martinelli de Oliveira, (2004), Biological evaluation of some selected cyclic imides: mitochondrial effects and in vitro cytotoxicity, Z. Naturforsch, 59c, 663-672.
Allen S. E. and Skoog F., (1950), Stimulation of seedling growth by seed treatments with N-phenyl succinimide derivatives, American Society of Plant Biologist, 179-183.
Pekalaa E., Lianaa P., Kubowicza P., Powroznika B., Obniska J., Chebekb I., Wegrzync A. and Wegrzyn G., (2013), Evaluation of mutagenic and anti-mutagenic properties of new derivatives of pyrrolidine-2, 5-dione with anti-epileptic activity, by use of the Vibrio harveyi mutagenicity, Mutation Research, 758, 18-22.
J. Alan Girdwood and Richard E. Shute, (1997), Solid-phase synthesis of tri-functionalized, a-substituted carbamoyl methyl homocysteine compounds, their release from the resin and subsequent intra-molecular cyclisation to give novel 1, 3, 3-trisubstituted succinimides, Chemical Communications, 2307-2308.
Anja Hoffmann-Roder, Paul Seiler and François Diederich, (2004), Nucleophilic trifluoromethylation of cyclic imides using (trifluoromethyl) trimethylsilane CF3SiMe3, Organic and Bio molecular Chemistry, 2, 2267-2269.
Bo-Liang Zhao and Da-Ming Du, (2014), Chiral squaramide-catalysed one-pot enantioselective sulfa-Michael addition or thioesterification of thiols with α, β- unsaturated N-acylated succinimides, Organic and Bio molecular Chemistry, 12, 1585-1594.
Benito Alcaide, Pedro Almendros, Gema Cabrero and M. Pilar Ruiz, (2007), Direct organocatalytic synthesis of enantiopure succinimides from b-lactam aldehydes through ring expansion promoted by azolium salt pre-catalysts, Chemical Communications, 4788-4790.
Gopa Barman, Mahuya Roy, Jayanta. K. Ray, (2008), A novel synthetic approach towards N-phenylsuccinimides from c-lactam-2-carboxylic acid derivatives by reaction with CAN–NaBrO3, Tetrahedron Letters 49, 1405-1407.
Anima Bose and Prasenjit Mal, (2014), Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling, Tetrahedron Letters, 55, 2154-2156.
Rajput S. S. (2012), Synthesis and characterization of bis-heteroyclic derivatives of 1-(3-chlorophenyl) - pyrrolidine-2, 5-dione, International Journal of Advances in Pharmacy, Biology and Chemistry, 1(2), 242-246.
Dhivare R. S. and Rajput S. S., (2015), Synthesis and antimicrobial activity of five membered cyclic imide derivatives of mono, di and tri substituted aromatic amines and napthyl amine, World Journal of Pharmaceutical Research, 49(6), 1650-1658.
Qinglei Chong, Chunxiang Wang, Dongping Wang, Haolong Wang, Fan Wu, Xiaoyi Xin and Boshun Wan, (2015), DABCO-catalyzed synthesis of 3-bromo-/3-iodo-2H-pyrans from propargyl alcohols, dialkyl acetylene dicarboxylates, and N-bromo-/N-iodosuccinimides, Tetrahedron Letters, 56, 401-403.
Sunil K. Upadhyay, Subramanya R. K. Pingali and Branko S. Jursic, (2010), Comparison of microwave-assisted and conventional preparations of cyclic imides, Tetrahedron Letters, 51, 2215-2217.