79558-91-1Relevant academic research and scientific papers
Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles
Duangkamol, Chuthamat,Pattarawarapan, Mookda,Phakhodee, Wong
, p. 1981 - 1990 (2020/07/03)
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.
One-pot reaction for the synthesis of N-substituted 2-aminobenzoxazoles using triphenylbismuth dichloride as cyclodesulfurization reagent
Murata, Yuki,Matsumoto, Natsuho,Miyata, Maya,Kitamura, Yuki,Kakusawa, Naoki,Matsumura, Mio,Yasuike, Shuji
, p. 18 - 23 (2018/02/09)
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.
Synthesis and evaluation of benzoxazole derivatives as 5-lipoxygenase inhibitors
Song, Hyunmin,Oh, Sei-Ryang,Lee, Hyeong-Kyu,Han, Gyoonhee,Kim, Joo-Heon,Chang, Hyeun Wook,Doh, Kyung-Eun,Rhee, Hee-Kyung,Choo, Hea-Young Park
experimental part, p. 7580 - 7585 (2011/01/04)
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
STUDIES ON HETEROCYCLIC COMPOUNDS. XXXIV. SYNTHESIS OF 2-SUBSTITUTED AMINOBENZOXAZOLES WITH NICKEL PEROXIDE
Ocura, Haruo,Mineo, Satoshi,Nakagawa, Kunio
, p. 1518 - 1524 (2007/10/02)
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
