Formation of polymer-modified electrodes from 2-mercaptobenzoxazole in aqueous solution

Berlich, Andrea; Flemmig, Beate; Wittstock, Günther

doi:10.1007/s100080000186

Cited by 12 publications

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“…In Figure , curve c is the voltammogram of 2-mercaptobenzothiazole ( 2a ). Wittstock and co-workers reported that the main product in the oxidation of 2-mercaptobenzoxazole is bis(benzoxazolyl) disulfide …”

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“…Wittstock and co-workers reported that the main product in the oxidation of 2-mercaptobenzoxazole is bis(benzoxazolyl) disulfide. 37 The overall reaction mechanism for the anodic oxidation of 4-morpholinoaniline (1) in the presence of 2-mercaptobenzothiazole (2a) is an ECCEC mechanism. In intramolecular nucleophilic substitution reaction, the −NH 2 group at the intermediate 5a attacks the carbon linked to sulfur in benzothiazole moiety and via a rearrangement converts to thiol 6a.…”

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Electrochemical Method for the Synthesis of Disulfides of 2-(Benzo[d]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzenethiol

Esmaili

Nematollahi

2013

J. Org. Chem.

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Electrochemical synthesis of two new disulfides of 2-(benzo[d]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzene thiols was carried out via the electrooxidation of 4-morpholinoaniline in the presence of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole. Our results indicate that electrogenerated p-quinonediimine participated in a Michael-type addition reaction with 2-SH-benzazoles and after intramolecular nucleophilic substitution reaction and electrooxidative disulfide bond formation were converted to the corresponding disulfide compounds.

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Electrochemical Method for the Synthesis of Disulfides of 2-(Benzo[d]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzenethiol

Esmaili

Nematollahi

2013

J. Org. Chem.

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“…Considering closeness of oxidation potential peaks of 4- tert -butylcatechol ( 1c ) and 2-mercaptobenzoxazole ( 3 ) (Figure ), to minimize the oxidation of 2-mercaptobenzoxazole ( 3 ) and hence achieving higher selectivity, we applied 0.10 V potential versus SCE in both coulometry and preparative synthesis processes. Wittstock and co-workers reported that the main product in oxidation of 2-mercaptobenzoxazole ( 3 ) is bis(benzoxazolyl) disulfide …”

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Electroorganic Synthesis of Catecholthioethers

2005

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[reaction: see text] It is demonstrated that o-quinones, generated by the electrochemically driven oxidation of the catechols (1a-d) at physiological pH, are rapidly scavenged by 2-mercaptobenzoxazole (3) to give related catecholthioethers (4a-d) via an EC electrochemical mechanism pathway. The electrochemical syntheses of 4a-d have been successfully performed in one-pot in ambient conditions and in an undivided cell using an environmentally friendly method with high atom economy.

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“…In addition, similar to the oxidation of 2‐mercaptobenzoxazole, which leads to the formation of bis(benzoxazolyl) disulfide [24], 2‐mercaptobenzimidazole ( 3 ) can be oxidized to the corresponding disulfide [Fig. (I), curve c], and the anodic peak (A 2 ) appeared at 0.53 V can be assigned for the oxidation of 3 .…”

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An Efficient, One‐Pot, Green Synthesis of Tetracyclic Imidazo[2,1‐b]Thiazoles via Electrochemically Induced Tandem Heteroannulation Reactions

Khodaei

Alizadeh

Kanjouri

2013

Journal of Heterocyclic Chem

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A series of novel catechol‐fused tetracyclic compounds, with an imidazo[2,1‐b]thiazole central core, were successfully synthesized through the anodic oxidation of catechols in the presence of 2‐mercaptobenzimidazole in aqueous solution. The cyclic voltammetric results indicate that a one‐pot four‐step sequential reaction occurs between 2‐mercaptobenzimidazole and the electrochemically derived o‐benzoquinones affording fused polyheterocyclic compounds. The mechanism of this catalyst‐free, domino reaction is proved as an ECEC pathway using controlled‐potential coulometry. In addition, the electrosyntheses of fused compounds have been successfully performed in ambient conditions in an undivided cell using an environmentally friendly method with high atom economy. The structures of products were characterized by FT‐IR, 1H NMR, 13C NMR, and HRMS spectrometric methods.

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Formation of polymer-modified electrodes from 2-mercaptobenzoxazole in aqueous solution

Cited by 12 publications

References 0 publications

Electrochemical Method for the Synthesis of Disulfides of 2-(Benzo[d]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzenethiol

Electrochemical Method for the Synthesis of Disulfides of 2-(Benzo[d]thiazol(or oxazol)-2-ylamino)-5-morpholinobenzenethiol

Electroorganic Synthesis of Catecholthioethers

An Efficient, One‐Pot, Green Synthesis of Tetracyclic Imidazo[2,1‐b]Thiazoles via Electrochemically Induced Tandem Heteroannulation Reactions

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