Research Article

Convenient route synthesis of some new benzothiazole derivatives and their pharmacological screening as antimicrobial agents

Ahmed A Fadda*, Nanees N Soliman and Ahmed Fekri

Published: 08/29/2017 | Volume 1 - Issue 1 | Pages: 032-046


Background: The reaction of 2-(benzo]d[thiazol-2-yl)-3-oxopentanedinitrile 4 with DMF/DMA has been investigated to explore the synthetic potentialities of this novel activated nitrile in heterocyclic synthesis.

Results: Pyrano, pyridino, pyrazolo, azepino and oxothiepano carbonitrile derivatives could be obtained starting from 4 and plausible mechanisms for their formations are reported.

Conclusion: The newly synthesized compounds were assessed for their antimicrobial activity. Compounds 7, 10 and 12 exhibited broad spectrum antibacterial profile against the tested organisms.

Read Full Article HTML DOI: 10.29328/journal.aac.1001004 Cite this Article


  1. Papesch V, Schroeder E. Synthesis of 1 Mono and 1,3 Di Substituted 6 Amino Uracils. Diuretic Activity 1. J Org Chem. 1951; 16: 1879-1890. Ref.:
  2. Muller T, Augustin M, Werchan HGZ. Zur Nitrosierung N′-aryl-substituierter N-Cyanacetyl-harnstoffe; Ringschluß und -transformation von Uracil-Derivaten. Zeitschrift für Chemie, 1989; 29: 281-283. Ref.:
  3. Isobe Y, Tobe M, Inoue Y, Isobe M, Tsuchiya M, et al. Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents. Bioorg Med Chem 2003; 11: 4933-4940. Ref.:
  4. Kappe T, Stelzel HP, Ziegler E. Synthese von Pyridonen aus Enaminen und Cyanessigsäuren. Montsh Chem. 1983; 114: 953-963. Ref.:  
  5. Stetinova J, Kada R, Lesko J, Zalibera L, Ilavský D et al. Synthesis and properties of substituted 1-(2-benzothiazolyl)-2-pyridones. Collect Czech Chem Commun. 1995; 60: 999-1008. Ref.:
  6. Al-Lohedan H, Bunton CA. Micellar effects upon the ElcB mechanism of ester hydrolysis. J Org Chem. 1981; 46: 3929-3930. Ref.:
  7. Refat HM, Fadda AA. Synthesis and Cytotoxicity Activity of Some Novel Hydrazide, Pyrazole, Isoxazole, Pyrimidine and Fused Pyran-2-one Derivatives. Heterocycles. 2015; 91: 1212-1226. Ref.:
  8. Fadda AA, El-Mekawy RE, El-Shafei AI. Synthesis, antiviral, cytotoxicity and antitumor evaluations of A4 type of porphyrin derivative. J Porphirins Phthalocyanins. 2015; 19: 753-768. Ref.:
  9. Fadda AA, Amer FA, Zaki MEA. Revised synthesis of some new 2-heterocyclic benzothiazolyl derivatives of biological interest. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 155: 59-66. Ref.:
  10. Fadda AA, Abdelrazek FM, Mohamed KS, Mostafa HM, Etman HA, et al. Synthetic applications of benzothiazole containing cyanoacetyl group. Eur J Chem. 2010; 1: 90-95. Ref.:
  11. Mohamed KS, Abdulaziz NM, Fadda AA. Synthesis of New Heterocyclic rings Containing Benzothiazole Moiety. J Heterocycl Chem. 2013; 50: 650-653. Ref.:
  12. Mohamed KS, Abdulaziz NM, Fadda AA. Synthesis of Some New Pyridine and Pyrimidine Derivatives Containing Benzothiazole Moiety. J Heterocycl Chem. 2013; 50: 645-649. Ref.:
  13. Fadda AA, Hammouda M, Afsah EM. Nitriles in Organic Synthesis: Synthesis of New Benzothiazole Derivatives of Biological Interest. Phosphorus, Sulfur Silicon Relat Elem. 2010; 185: 433-446. Ref.:
  14. Fadda AA, Abdel-latif E, Bondock S. Synthesis of Some New Pyrimidine and Pyrimido [4,5-d] pyrimidine Derivatives. Synth Commun. 2008; 38: 4352-4368. Ref.:
  15. Fadda AA, Zaki MEA, Mohamed KS, Amer FA. Nitriles in Organic Synthesis: Synthesis of Some New 2-Heterocyclic Benzothiazol Derivatives. Phosphorus Sulfur Silicon Relat Elem. 2007; 182: 1845-1856. Ref.:
  16. Zaki MEA, Fadda AA, Mohamed KS. Nitriles in Organic Synthesis: A Convenient Route to Some Heterocycles Incorporating a Benzothiazole Moiety. Phosphorus Sulfur Silicon Relat Elem. 2006; 181: 1815-1823. Ref.:
  17. Zaki MEA, Fadda AA, Samir K, Amer FA. Nitriles in Organic Synthesis: Synthesis of Pyrido[2,1-b]Benzothiazole Derivatives and Polyfunctionally Substituted Pyridines. Chem Heterocycl Compd. 2003; 39: 1242-1248. Ref.:
  18. Abdel-latif E, Mustafa HM, Etman HA, Fadda AA. Synthesis of new Purin, Pteridine and other Pyrimidine Derivatives. Russ J Org Chem. 2007; 43: 443-448. Ref.:
  19. Fadda AA, Refat HM, Mohamed, KS. Synthesis and Antimicrobial Evaluation of Some New Dihydropyridine, Pyrazole, Chromene, Pyrrole, Thiazole and Thiophene Derivatives. Heterocycles. 2014; 89: 2318-2333. Ref.:
  20. Bondock S, Khalifa W, Fadda AA. Synthesis and Antimicrobial Evaluation of Some New Thiazole, Thiazolidinone and Thiazoline Derivatives Starting from 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem. 2007; 42: 948-954. Ref.:
  21. Abo-Melha H, Fadda AA. Synthesis, spectral characterization and in vitro antimicrobial activity of some new azopyridine derivatives. Spectrochim Acta Part A. 2012; 89: 123-128. Ref.:
  22. Fadda AA, Zaki M, Mohamed KS, Samir K, Etman HA. Chemistry of 2-Cyanomethyl-benzothiazole. Phosphorus, Sulfur Silicon Relat Elem. 2008; 183: 1801-1842. Ref.: