Mercaptotriazole as a nucleophile in addition to o-quinone electrochemically derived from catechol: application to electrosynthesis of a new group of triazole compounds

Abstract Electrochemical oxidation of catechol in the presence of 3-mercapto-1,2,4-triazole (MTA) as a nucleophile in aqueous buffered solutions was studied by cyclic voltammetry and controlled-potential coulometry. The mechanism of electrochemical reaction is confirmed by spectrophotometric tracing in various times of controlled-potential coulometry. The voltammetric and spectrophotometric foundations indicate that a 1,4 Michael addition of MTA from its thiol moiety to the electrochemically derived o -quinone is occurred. The electrochemical synthesis of Michael addition product has been successfully accomplished by controlled-potential coulometry in a divided H-type cell and the reaction product was characterized by spectrophotometric, 1 H and 13 C NMR, elemental analysis and mass spectrometric methods.

[1]  F. Sa̧czewski,et al.  A new type of mixed anhydride and its applications to the synthesis of 7-substituted 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazines with in vitro antitumor activity. , 2002, Journal of medicinal chemistry.

[2]  M. Kazemi,et al.  Mechanistic study of the oxidation of catechol in the presence of secondary amines by digital simulation of cyclic voltammograms , 2004 .

[3]  R. K. Saxena,et al.  Microwave assisted solid support synthesis of novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines as potent antimicrobial agents. , 2001, Bioorganic & medicinal chemistry.

[4]  B. Poojary,et al.  Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. , 2003, European journal of medicinal chemistry.

[5]  Alfonso R. Gennaro,et al.  Remington:the science and practice of pharmacy , 1995 .

[6]  R. R. Moore,et al.  Electrocatalytic detection of thiols using an edge plane pyrolytic graphite electrode. , 2004, The Analyst.

[7]  P. C. White,et al.  Electrochemically Driven Derivatisation-Detection of Cysteine , 2001 .

[8]  C. Livingstone,et al.  Potentiometric detection of thiols: a mechanistic evaluation of quinone-thiol interactions , 2003 .

[9]  N. Lawrence,et al.  Selective Electroanalytical Assay for Cysteine at a Boron Doped Diamond Electrode , 2004 .

[10]  N. Lawrence,et al.  Electrochemical detection of thiols in biological media. , 2001, Talanta.

[11]  P. C. White,et al.  Electrochemically initiated 1,4 additions: a versatile route to the determination of thiols , 2001 .

[12]  D. Nematollahi,et al.  Investigation of the electro-methoxylation reaction: Part 1. Electrochemical study of 4-tert-butylcatechol and 3,4-dihydroxybenzaldehyde in methanol , 2000 .

[13]  A. Samadi-Maybodi,et al.  Mechanistic study of electrochemical oxidation of 4-tert-butylcatechol: A facile electrochemical method for the synthesis of new trimer of 4-tert-butylcatechol , 2004 .

[14]  M. Rafiee,et al.  Electrochemical oxidation of catechols in the presence of acetylacetone , 2004 .

[15]  W. Stigelman,et al.  Goodman and Gilman's the Pharmacological Basis of Therapeutics , 1986 .

[16]  S. Shahrokhian,et al.  Electrochemical oxidation of catechol in the presence of 2-thiouracil: application to electro-organic synthesis , 2003 .

[17]  Nouri Neamati,et al.  Application of CoMFA and CoMSIA 3D-QSAR and docking studies in optimization of mercaptobenzenesulfonamides as HIV-1 integrase inhibitors. , 2004, Journal of medicinal chemistry.

[18]  J. Coulon,et al.  1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents. , 2003, Bioorganic & medicinal chemistry letters.