79558-93-3

Upstream product

• 79558-91-1 N-(2-hydroxy-5-methylphenyl)-N'-phenylthiourea 
• 103-72-0 phenyl isothiocyanate 
• 95-84-1 3-amino-4-hydroxytoluene 

Relevant academic research and scientific papers

Microwave-assisted hydrogen peroxide-mediated synthesis of benzoxazoles and related heterocycles via cyclodesulfurization

A novel approach has been developed to construct benzoxazoles and similar N- and S-containing heterocycles from their corresponding isothiocyanates and o-substituted anilines via cyclodesulfurization. The reaction was found to proceed via in situ formatio

Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by: Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles

A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho -substituted anilines bearing N, N -, N, O -, and N, S -bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.

Iodide catalyzed synthesis of 2-aminobenzoxazoles via oxidative cyclodesulfurization of phenolic thioureas with hydrogen peroxide

A convenient and efficient oxidative cyclodesulfurization of o-phenolic thioureas to 2-aminobenzoxazoles employing TBAI (tetrabutylammonium iodide)/H2O2 catalyst/reagent system is reported. The protocol utilizes and offers a number o

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.

Visible-light-promoted cyclodesulfurization of phenolic thioureas: An organophotoredox catalytic approach to 2-aminobenzoxazoles

A facile and efficient one-pot operation for the photo-oxidative cyclodesulfurization of o-phenolic thioureas to afford 2-aminobenzoxazoles is reported. The protocol could be executed under visible light irradiation employing eosin Y as an organophotoredo

An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water

Tandem reactions of isothiocyanates (1) with 2-aminothiophenols (2), or isothiocyanates (1) with 2-aminophenols (4), were carried out rapidly and efficiently in water. A significant rate acceleration of the reaction between 1a and 2a in water compared wit

Synthesis and evaluation of benzoxazole derivatives as 5-lipoxygenase inhibitors

5-Lipoxygenase (5-LOX) is important enzyme in the biosynthesis of leukotrienes, and is a potential target in the treatment of asthma and allergy. We designed and synthesized a series of benzoxazoles and benzothiazoles as 5-LOX inhibitors. Fourteen compoun

Facile Synthesis of 2-Substituted Aminobenzoxazole. One Pot Cyclodesulfurization of N-(2-Hydroxyphenyl)-N'-phenylthioureas with Superoxide Radical Anion

Treatment of N-(2-hydroxyphenyl)-N'-phenylthioureas with the superoxide radical anion (O2-.) at 20 deg C in CH3CN, THF, or DMSO resulted in the formation of 2-substituted aminobenzoxazoles in excellent yields.

STUDIES ON HETEROCYCLIC COMPOUNDS. XXXIV. SYNTHESIS OF 2-SUBSTITUTED AMINOBENZOXAZOLES WITH NICKEL PEROXIDE

Oxidation of N-methyl (or phenyl)-N'-(4-methylpyrid-2-yl)thiourea (Ia, b) with nickel peroxide (Ni-PO) under reflux in benzene or acetonitrile afforded the corresponding ureas (IIa, b).N-(2-Hydroxy-5-methylphenyl)-N'-methylthiourea (IVa) was synthesized by the reaction of 2-amino-4-methylphenol (III) and methyl isothiocyanate in benzene under reflux.Howevwer, the reaction of III and phenyl isothiocyanate in benzene under reflux did not afford the thiourea (IVb) but IVb was obtained in ethanol at room temperature.NiPO oxidation of thioureas (IVa-f) in acetonitrile at room temperature afforded 2-substituted aminobenzoxazoles (VIIa-f) in good yields.The reaction mechanisms of Ni-PO and thioureas (Ia, b and IVa-f) are discussed.Keywords: - N-substituted N'-(4-methylpyrid-2-yl)thioureas; N-substituted N'-(4-methylpyrid-2-yl)ureas; N-(2-hydroxyphenyl) N'-substituted thioureas; 2-substituted aminobenzoxazoles; nickel peroxide; oxidative cyclization; 2-mercaptobenzoxazole; isothiocyanates