31428-76-9Relevant academic research and scientific papers
Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes
Tanii, Saori,Arisawa, Mieko,Tougo, Takaya,Yamaguchi, Masahiko
, p. 1756 - 1759 (2018/04/14)
C-N-linked bi(heteroaryl)s are synthesized by a rhodium-catalyzed N-heteroarylation reaction of N-benzoyl heteroarenes including azoles/azolones, pyridones, cyclic ureas, and cyclic imides using heteroaryl aryl ethers. The reaction involves the covalent bond-exchange reaction of N-CO and HetAr-O bonds without using metal bases and exhibits a broad applicability, giving diverse C-N-linked bi(heteroaryl)s containing five- and six-membered heteroarenes. The N-heteroarylation of N-H azoles/azolones and pyridone proceeds at higher reaction temperatures.
Design and synthesis of 3-acyl-2(3H)-benzoxazolone and 3-acyl-2(3H)- benzothiazolone derivatives
Guenadil, Faouzi,Aichaoui, Hocine,Kapanda, Coco N.,Lambert, Didier M.,McCurdy, Christopher R.,Poupaert, Jacques H.
experimental part, p. 67 - 80 (2011/09/20)
A simpler and efficient "green" method using solid sodium hydroxide in a solvent mixture of acetone/water was found to catalyze N-acylation of 2(3H)-benzoxazolones and 2(3H)-benzothiazolones for facile and rapid synthesis of N-acyl derivatives in excellent yields. This method was applied to the synthesis of a series of 132 compounds employing a variety of acyl chlorides. Graphical abstract: [Figure not available: see fulltext.]
Efficient and selective deprotection method for N-protected 2(3H)-benzoxazolones and 2(3H)-benzothiazolones
Carato, Pascal,Yous, Sa?d,Sellier, Didier,Poupaert, Jacques H.,Lebegue, Nicolas,Berthelot, Pascal
, p. 10321 - 10324 (2007/10/03)
Cyclic carbamate flanked with heterocyclic or aliphatic moieties are frequently used in medicinal chemistry. The synthesis of derivatives bearing a free NH often requires the use of a protection method. A literature search reveals very few protection/deprotection methods for cyclic carbamates. In this paper, we described different methods applicable to 2(3H)-benzoxazolone and 2(3H)-benzothiazolone. Graphical abstract
Application of the "fries like" rearrangement using ZnCL 2 for the synthesis of 6-acyl-2(3H)-benzothiazolones
Guenadil, Faouzi,Aichaoui, Hocine
, p. 1703 - 1708 (2007/10/03)
In this work we report another method of acylation on the 6-position of the 2(3H)-benzothiazolone ring with Fries-like rearrangement catalyzed by zinc chloride instead of aluminium chloride and 3-acyl-2(3H)-benzothiazolones derivatives as starting materia
Synthesis and anticonvulsant activity of 2(3H)-benzoxazolone and 2(3H)- benzothiazolone derivatives
Ucar, Huseyin,Van Derpoorten, Kim,Cacciaguerra, Silvia,Spampinato, Santi,Stables, James P.,Depovere, Paul,Isa, Majed,Masereel, Bernard,Delarge, Jacques,Poupaert, Jacques H.
, p. 1138 - 1145 (2007/10/03)
A series of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives were synthesized and evaluated for anticonvulsant activity. The compounds were assayed, intraperitoneally in mice and per os in rats, against seizures induced by maximal electroshock (MES) and pentylene-tetrazole (scMet). Neurologic deficity was evaluated by the rotarod test. The compounds were prepared to determine the relationship between the 2(3H)-benzoxazolone and 2(3H)-benzothiazolone derivatives' structures and anticonvulsant activity. Several of these compounds showed significant anticonvulsant activity. Compounds 43 and 45 were the most active of the series against MES-induced seizures with ED50 values of 8.7 and 7.6 mg/kg, respectively. Compound 45 displayed good protection against MES-induced seizures and low toxicity in rats with an oral ED50 of 18.6 mg/kg and a protective index (PI = TD50/ED50) of 1 receptors with nanomolar affinities.
Synthesis of 6-benzoyl-2(3H)-benzoxazolone and 6-benzoyl-2(3H)-benzothiazolone
Ucar, Huseyin,derpoorten, Kim Van,Kanyonyo, Martial,Isa, Majed,Lambert, Didier,et al.
, p. 773 - 776 (2007/10/03)
This paper reports and compares different methods to synthesize 6-benzoyl-2(3H)-benzoxazolone and 6-benzoyl-2(3H)-benzothiazolone by Friedel-Crafts acylation of 2(3H)-benzoxazolone and 2(3H)-benzothiazolone.The best method found consisted of the transposition of the N-benzoyl derivative to the target compound, a process taking place at 160 deg C and catalyzed by AlCl3.In these conditions, 6-benzoyl-2(3H)-benzoxazolone and 6-benzoyl-2(3H)-benzothiazolone were obtained in 80 and 85 percent yield, respectively.
