The Synthesis of Aminobenzothiazoles from 2,3‐Biaryl‐5‐anilino‐Δ³‐1,2,4‐thiadiazolines.

Abstract

Benzothiazole derivatives Benzothiazole derivatives R 0270The Synthesis of Aminobenzothiazoles from 2,3-Biaryl-5-anilino-∆ 3 -1,2,4-thiadiazolines. -2,3-Biaryl-5-anilino-∆ 3 -1,2,4-thiadiazolium bromides (I) undergo a thermally-promoted rearrangement forming 2-amidinobenzothiazoles (II). In some cases, the yield can be improved by adding a base. -(PAN*, K.; REITZ, A. B.; Synth.

Synthesis and Biological Evaluation of a New Series of 2,3,5-Substituted [1,2,4]-Thiadiazoles as Modulators of Adenosine A1 Receptors and Their Molecular Mechanism of Action

“…The stability and reactivity of other thiadiazoles have been studied by several authors. Pan et al have demonstrated that thiadiazoles bearing aryl R 2 substituents shown to be active as melanocortin MC4 receptor agonists may undergo a thermal rearrangement to 2-amidinobenzothiazole in DMSO. , The same authors reduced 2-(4-methylphenyl)-3-phenyl-5-(4-methoxyphenylamino)-[1,2,4]-thiadiazolium bromide to its precursor imidoylthiourea by dithioerythritol. They suspected that this compound also reacts with the thiol group on cysteine residues or that it oxidizes two thiol groups to create a disulfide bond, causing irreversible binding to the receptor .…”