405934-28-3

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 128814-70-0 N-phenyl-4H-benzo[d][1,3]oxazin-2-amine 
• 109768-66-3 N-phenyl-4H-benzo[d][1,3]thiazin-2-amine 

Relevant academic research and scientific papers

A Bench-Stable Vilsmeier Reagent for in situ Alcohol Activation: Synthetic Application in the Synthesis of 2-Amino-2-Thiazolines

A robust, chemoselective direct condensation/cyclization of thioureas and amino alcohols is described. Employing a bench-stable Vilsmeier reagent, methoxymethylene- N, N -dimethyliminium methyl sulfate, the selective in situ activation of alcohols is achieved with high efficiency and broad functional-group tolerance. The reversible interaction of the Vilsmeier reagent with substrate was key to the success of this activation strategy.

A Facile Synthesis of 2-Aminobenzoxazines Based on Iodine-Catalyzed Desulfurative Cyclization

A facile and environmentally benign access to N-aryl/alkyl-4H-benzoxazin-2-amines is achieved from 1-[2-(hydroxymethyl)phenyl/alkyl]-3-phenylthioureas under transition-metal-free conditions. The conversions occur smoothly in the presence of a catalytic amount of molecular iodine and hydrogen peroxide as the oxidant in tetrahydrofuran at room temperature to afford moderate to good yields (28-90%) of the desired products within 2 hours. This method reports the first examples of the catalytic transformations of 1-[2-(hydroxymethyl)phenyl/alkyl]-3-phenylthioureas into N-aryl/alkyl-4H-benzoxazin-2-amines based on desulfurative cyclization.

P(III)-Mediated Cascade C-N/C-S Bond Formation: A Protocol towards the Synthesis of N,S-Heterocycles and Spiro Compounds

A P(III)-mediated entry towards construction of C?N/C?S bond has been devised. The developed heterocyclization method was exercised for the synthesis of a diverse range of N,S-heterocycles and related spiro molecules. P(NMe2)3 revealed the maximum efficacies under the aerobic reaction conditions and a spectrum of bis-nucleophiles, and isothiocyanates were tolerated well to serve the access of manifold immense molecules. (Figure presented.).

Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines

A reagent-controlled chemoselective process has been devised for the synthesis of 4H-1,3-benzoxazines and related biologically important heterocycles in high yields under mild conditions. These scaffolds could be efficiently constructed using two different chemoselective reactions that rely on the choice of reagents and reaction conditions. The treatment of various 2-amino-arylalkyl alcohols with isothiocyanates afforded thiourea intermediates, which were reacted in situ with molecular iodine in the presence of triethylamine to give 2-amino-4H-1,3-benzoxazines, whereas the corresponding 2-amino-4H-1,3-benzothiazines were obtained by the reaction of thiourea intermediates in the presence of T3P (a mild cyclodehydrating agent) and triethylamine as the base. The described protocol represents the first example for the synthesis of 4H-1,3-benzoxazines via the dehydrosulfurization method using molecular iodine as the reagent.

One-pot reaction for the synthesis of N-substituted 2-aminobenzoxazoles using triphenylbismuth dichloride as cyclodesulfurization reagent

The treatment of various 2-aminophenols with isothiocyanates afforded thioureas, which were reacted in situ with triphenylbismuth dichloride in the presence of triethylamine to give the expected N-substituted benzoxazol-2-amines in good to excellent yields. Triphenylbismuth dichloride promoted the successful cyclodesulfurization of thioureas with short reaction times under mild reaction conditions. This reaction is the first example of the synthesis of heterocyclic rings using a pentavalent organobismuth reagent.