Microwave irradiation: synthesis and characterization of α-ketoamide and bis (α-ketoamide) derivatives via the ring opening of N-acetylisatin

详细信息    查看全文

• 作者：Ayman El-Faham ; Sherine N Khattab ; Hazem A Ghabbour…
• 关键词：N ; acetylisatin ; N ; propionylisatin ; Microwave irradiation ; α ; ketoamide ; bis ; α ; ketoamide ; X ; ray crystallography
• 刊名：Chemistry Central Journal
• 出版年：2014
• 出版时间：December 2014
• 年：2014
• 卷：8
• 期：1
• 全文大小：329 KB
• 参考文献：1. Lidstrom, , Tierney, J, Wathey, B, Westman, J (2001) Microwave assisted organic synthesis—a review. Tetrahedron 57: pp. 9225-9283 CrossRef
  2. Perrux, L, Loupy, AA (2001) A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 57: pp. 9199-9223 CrossRef
  3. Adam, D (2003) Microwave Chemistry: Out of the Kitchen. Nature 421: pp. 571-572 CrossRef
  4. Loupy, A (2004) Solvent-free microwave organic synthesis as an efficient procedure for green chemistry. Chimie 7: pp. 103-112 CrossRef
  5. Matloobi, M, Kappe, CO (2007) Microwave Synthesis in High-Throughput Environments. Moving from Automated Sequential to Microtiter Plate Formats. Chim Oggi 25: pp. 26-31
  6. Mallakpour, S, Rafiee, Z (2008) Application of microwave-assisted reactions in step-growth polymerization: A review. Iran Polym J 17: pp. 907-935
  7. Raval, JP, Desai, KG, Desai, KR (2006) Neat reaction technology for the synthesis of 4-Oxo-thiazolidines derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized 4-thiazolidinones. J Iranian Chem Soc 3: pp. 233-241 CrossRef
  8. Raval, JP, Desai, JT, Desai, CK, Desai, KR (2008) A comparative study of microwave assisted and conventional synthesis of 2,3-dihydro-2-aryl-4-[4-(2–oxo-H–chromen-–yl)-,3-thiazol-–ylamino]-1,5–benzothiazepines and its antimicrobial activity. Arkivoc xii: pp. 233-244 CrossRef
  9. Raval, JP, Desai, KR (2009) A comparative study of microwave-assisted and conventional synthesis of novel 2-(4-diethylamino-2-hydroxyphenyl)-3-substituted-thiazolidin-4-one derivatives. Lietuvos Mokslu Akademija 20: pp. 101-108
  10. Raval, JP, Patel, HV, Patel, PS, Patel, NH, Desai, KR (2009) A rapid convenient microwave assisted and conventional synthesis of novel azetidin-2-one derivatives as potent antimicrobial agents. Asian J Res Chem 2: pp. 171-177
  11. Al-Hazimi, HM, El-Faham, A, Ghazzali, M, Al-Farhan, K (2012) Microwave irradiation: A facile, scalable and convenient method for synthesis of N-phthaloylamino acids. Arabian J Chem 5: pp. 285-289 CrossRef
  12. Ghazzali, M, El-Faha, A, Abd-Megeed, A, Al-Farhan, K (2012) Microwave-assisted synthesis, structural elucidation and biological assessment of 2-(2-acetamidophenyl)-2-oxo-N-phenyl acetamide and N-(2-(2-oxo-2(phenylamino)acetyl)phenyl)propionamide derivatives. J Mol Str 1013: pp. 163-167 CrossRef
  13. Charde, M, Shukla, A, Bukhariya, V, Mehta, J, Chakole, R (2012) A Review on: A significance of microwave assist technique in green chemistry. Int J Phytopharm 2: pp. 39-50
  14. Ravichandran, S, Karthikeyan, E (2011) Microwave Synthesis - A Potential Tool for Green Chemistry. Int J Chem Tech Res 3: pp. 466-470
  15. Da Silva, JFM, Garden, SJ, Pinto, AC (2001) The Chemistry of Isatins: a Review from 1975 to 1999. J Braz Chem Soc 12: pp. 273-324 CrossRef
  16. Cheah, WC, Black, DS, Goh, WK, Kumar, N (2008) Synthesis of anti-bacterial peptidomimetics derived from N-acylisatins. Tetrahedron Lett 49: pp. 2965-2968 CrossRef
  17. Obafemi, CA, Taiwo, FO, Iwalewai, EO, Akinpelu, DA (2012) Synthesis, Antibacterial And Anti-Inflammatory Activities Of Some 2-Phenylglyoxylic Acid Derivatives. Int J Life Sci & Pharma Res 2: pp. 22-36
  18. Hossain, MM, Islam, RM, Saha, SK, Islam, MK (2010) An efficient microwave-assisted synthesis of dihydropyrazinones and bis-benzoylketones. Tetrahedron Lett 51: pp. 1155-1157 CrossRef
  19. Andreani, A, Burnelli, S, Granaiola, M, Leoni, A, Locatelli, A, Morigi, R, Rambaldi, M, Varoli, L, Cremonini, MA, Placucci, G, Cerv
• 刊物类别：Chemistry and Materials Science
• 出版者：Chemistry Central Ltd
• ISSN：1752-153X

文摘

Background The carbonyl group at position 2 of N-acetylisatin behaves as an amide which is more susceptible to nucleophilic attack via ring-opening in the presence of nucleophiles. Because of this behavior, in the present work we describe the microwave synthesis of a series of α-ketoamide and bis-(α-ketoamide) derivatives via the facile ring-opening of N-acylisatin with different amines and diamines. The microwave irradiation afforded the product in less reaction time, higher yield and purity. Reaction of N-acylisatin with methanol under microwave irradiation afforded the α-phenylglyoxyl methyl ester derivatives with excellent yields and purities. Aminolysis of the ester derivatives with piperidine and morpholine afforded the same α-ketoamide derivatives obtained from direct aminolysis of N-acylisatin. The structures of the synthesized compounds were confirmed by FT-IR, NMR, X-ray and elemental analysis. Results Reaction of N-acetylisatin and N-propoionylsatin with different amines and diamines afforded a series of α-ketoamide and bis-(α-ketoamide) derivatives respectively via the ring opening of N-acylisatins. The reaction was performed under conventional condition as well as microwave irradiation. The microwave irradiation afforded the product in less reaction time, higher yield and purity. Reaction of N-acylisatin with methanol under microwave irradiation afforded the α-phenylglyoxyl methyl ester derivatives in excellent yields and purities as observed from their spectral data. A plausible mechanism involves nucleophilic attack by methanol at C2 carbonyl carbon of N-acetylisatin and subsequent ring opening to generate the α-ketoester. Aminolysis of α-ketoester with amine afforded the same α-ketoamide which is obtained by direct aminolysis of N-acylisatin. The IR, NMR spectra, microanalyses, and single crystal X-ray diffraction confirmed the structures of the synthesized compounds. Conclusions In conclusion, we have demonstrated that microwave irradiation could be employed efficiently for the synthesis of biologically important α-ketoamide and bis-(α-ketoamide) derivatives. The microwave irradiation has more advantageous over the classical method with regard to reaction time, solvent quantity, and product yield. Reaction of N-acylisatin with methanol under microwave irradiation afforded the α-phenylglyoxyl methyl ester derivatives with excellent yields and purities. Aminolysis of the methyl ester derivatives with amine under microwave irradiation afford the same α-ketoamide derivatives as obtained from direct aminolysis of N-acylisatins.