28953-24-4

Usage

InChI:InChI=1/C9H8N2O2S/c1-13-9(12)11-8-10-6-4-2-3-5-7(6)14-8/h2-5H,1H3,(H,10,11,12)

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 39982-28-0 methyl N-chlorolcarbamate 
• 35266-49-0 methoxycarbonylisothiocyanate 
• 1141-88-4 2-Aminophenyl disulfide 
• 136-95-8 2-amino-benzthiazole 
• 4542-30-7 benzothiazol-2-yl-carbamic acid 
• 74-88-4 methyl iodide 
• 79-22-1 methyl chloroformate 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of benzazolyl azolyl urea derivatives

A new class of benzazolyl azolyl urea derivatives were prepared by the reaction of methyl benzazoyl carbamates with azolyl amines in the presence of mild base potassium tert-butoxide. The presence of electron withdrawing substituents on the aromatic ring enhanced the activity. Nitro substituted benzothiazolyl thiazolyl urea, benzothiazolyl imidazolyl urea and benzimidazolyl thiazolyl urea exhibited potential antibacterial activity against Bacillus subtilis. The compound benzothiazolyl imidazolyl urea and nitro substituted benzimidazolyl imidazolyl urea showed potential antifungal activity against Aspergillus niger.

(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies

Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.

Unexpected formation of benzothiazoles in the synthesis of new heterocycles: Benzo-1,2,4-dithiazines

The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2′-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed procedure offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2′-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown. Georg Thieme Verlag Stuttgart.

Mild and convenient synthesis of organic carbamates from amines and carbon dioxide using tetraethylammonium superoxide

A safe and simple method of preparing organic carbamates has been achieved from amines and carbon dioxide using tetraethylammonium superoxide generated in situ. Copyright Taylor & Francis Group, LLC.