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Research Article Open access CC BY 3.0

Microwave-Assisted Synthesis, NMR, and Cyclic Voltammetric Study of Some Novel 3,5-Disubstituted 1H-1,2,4-Triazoles Containing Hetaryl Fragments

Yaseen A. Al-Soud, Ziad Moussa, Ali F. Al-Ghamdi

Chemical Science International Journal · pp. 1001–1013 · Published 23 Aug 2014

10.9734/ACSJ/2014/12036

Abstract

The synthesis of the title compounds 5a-c has been accomplished by a Suzuki cross coupling reaction between arylbromide 3 and 5-Indole boronic acid to furnished precursor 4, which was used as a key intermediate for the synthesis of the preceding targets. Thus, treatment of 4 with variously-substituted arylsulfonyl chlorides, the sulfonate derivatives 5a-c were obtained in good yields and high purity. The structures of 5a-c were characterized by 1H, 13C NMR, and liquid chromatography-mass spectroscopy techniques. Further, the electrochemical behavior of compound 5c has been investigated by cyclic voltammetry using Britton-Robinson (B-R) buffer at pH 3, pH 7 and pH 9, acetate buffer pH 3, and Phosphate buffer pH 3.  A broad anodic cyclic voltammetric wave at Eap= 640 mV was observed.  

Synthesis suzuki cross coupling 1, 2, 4-triazoles cyclic voltammetry

References (26)

  1. 1 Antiviral drugs in current clinical use [DOI]
  2. 2 New pyrazole derivatives containing 1,2,4-triazoles and benzoxazoles as potent antimicrobial and analgesic agents [DOI]
  3. 3 Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents [DOI]
  4. 4 Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles [DOI]
  5. 5 Design, Synthesis, Biological Evaluation and Pharmacokinetics of Bis(hydroxyphenyl) substituted Azoles, Thiophenes, Benzenes, and Aza-Benzenes as Potent and Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1) [DOI]
  6. 6 Triazole incorporated pyridazinones as a new class of antihypertensive agents: Design, synthesis and in vivo screening [DOI]
  7. 7 Synthesis and Antifungal Activity of 1,2,4-triazole Derivatives Containing Cyclopropane Moiety [DOI]
  8. 8 Development and validation of a specific stability indicating high performance liquid chromatographic method for rizatriptan benzoate [DOI]
  9. 9 New nitric oxide donating 1,2,4-triazole/oxime hybrids: Synthesis, investigation of anti-inflammatory, ulceroginic liability and antiproliferative activities [DOI]
  10. 10 The antiviral drug ribavirin is a selective inhibitor of S-adenosyl-l-homocysteine hydrolase from Trypanosoma cruzi [DOI]
  11. 11 Separation of 1,4-benzodiazepines by micellar elektrokinetic capillary chromatography [DOI]
  12. 12 Antimycobacterial and antimicrobial study of new 1,2,4‐triazoles with benzothiazoles [DOI]
  13. 13 Effect of 4-(4-bromophenyl)-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione on the anticonvulsant action of different classical antiepileptic drugs in the mouse maximal electroshock-induced seizure model [DOI]
  14. 14 Synthesis, characterization, and antimicrobial evaluation of some new hydrazinecarbothioamide, 1,2,4-triazole and 1,3,4-thiadiazole derivatives [DOI]
  15. 15 Synthesis and Biological Evaluation of Phenyl Substituted 1H‐1,2,4‐Triazoles as Non‐Steroidal Inhibitors of 17β‐Hydroxysteroid Dehydrogenase Type 2 [DOI]
  16. 16 Synthesis, Acidity and Antioxidant Properties of Some Novel 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives [DOI]
  17. 17 The role of the heterocycle in bis(hydroxyphenyl)triazoles for inhibition of 17β-Hydroxysteroid Dehydrogenase (17β-HSD) type 1 and type 2 [DOI]
  18. 18 Synthesis, Antifungal Activity, and Molecular Docking Studies of Novel Triazole Derivatives [DOI]
  19. 19 Steroidal aromatase inhibitors in elderly patients [DOI]
  20. 20 Synthesis and antioxidant activities of some 4-benzylidenamino-4,5-dihydro- 1 H -1,2,4-triazol-5-one derivatives
  21. 21 Preparation, GIAO NMR Calculations and Acidic Properties of Some Novel 4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives with Their Antioxidant Activities [DOI]
  22. 22 Synthesis and Antiviral Activity of 1-[(1,5-Dialkyl-1H-1,2,4-triazol-3-yl)methyl]thymines [DOI]
  23. 23 Electrochemical oxidation of 5-hydroxytryptamine in acidic acetonitrile [DOI]
  24. 24 DNA-directed alkylating agents: synthesis, antitumor activity and DNA affinity of bis-N,N′-trisubstituted 1,2,4-triazolo-piperazines [DOI]
  25. 25 Structural correction of the 3-methylindole oxidatively-coupled dimer [DOI]
  26. 26 Synthesis and antitumor activity of some new phthalimide analogues.

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