1437-77-0Relevant academic research and scientific papers
An improved and mild wenker synthesis of aziridines
Li, Xinyao,Chen, Ning,Xu, Jiaxi
experimental part, p. 3423 - 3428 (2010/11/21)
The conventional Wenker synthesis of aziridines from vicinal amino alcohols has been modified by employing mild reaction conditions. Amino alcohols were converted into their hydrogen sulfates with chlorosulfonic acid. The sulfates were cyclized with sodium hydroxide, and even with non-nucleophilic sodium carbonate. The current, improved method extends the scope of the typical Wenker synthesis and is applicable to unstable amino alcohols in hot sulfuric acid and to unstable sulfates which favor elimination and hydroxide displacement in the presence of strong base. Georg Thieme Verlag Stuttgart.
Synthesis and Biological Activity of 2-Aminothiazolines and 2-Mercaptothiazolines as Octopaminergic Agonists
Hirashima, Akinori,Yoshii, Yutuka,Eto, Morifusa
, p. 2537 - 2546 (2007/10/02)
2-Aminothiazoline derivatives were synthesized by both hydrochloric acid-catalyzed cyclization of thiourea and cyclization of β-aminoalkyl hydrogen sulfate with isothiocyanate in the presence of sodium hydroxide.Substituted 2-mercaptothiazoline derivatives were prepared by alkylation or acylation of the sodium salt of 2-mercaptothiazoline, which was obtained from β-aminoalkyl hydrogen sulfate with carbon disulfide. 2-(4-Chloro-o-toluidino)-2-thiazoline (III-16) was 33percent as effective as octopamine at 100 μM in stimulating adenylate cyclase of Periplaneta americana ventral-nerve-cord homogenates.Its activity was nonadditive to the activity of octopamine.Stimulation of nerve-cord adenylate cyclase activity by III-16 was inhibited by several antagonists, including mianserin, cyproheptadine, chlorpromazine and gramine.The rank-order ability of these antagonists to block the activation by III-16 was identical to the rank-order ability of the same antagonists to block enzyme activation of octopamine.The β-adrenergic antagonist propanolol was less potent.These data suggest that III-16 is a potent and selctive agonist of octopamine-activated adenylate cyclase.Aminothiazolines which activated adenylate cyclase by 10-87percent relative to octopamine also had acaricidal activity at 300 ppm, indicating a correlation between the in vitro octopaminergic-agonist activity and in vivo acaricidal activity of aminothiazolines.
