Metal-Free C–S Bond Cleavage to Access N-Substituted Acrylamide and β-Aminopropanamide
Metal-free and Selectfluor-mediated C–S bond cleavage is described. This novel strategy provides a facile and efficient method to access important N-substituted acrylamide and β-aminopropanamide derivatives with good functional group tolerance and yields.
Synthesis and antiallergic activity of dimethyl-2- (phenylcarbamoyl)ethylsulfonium p-toluenesulfonate derivatives
The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p- toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE- induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4- propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (±)-2-[N-[4-(3-ethoxy-2- hydroxypropoxy)phenyl]carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.
Tada, Yukio,Yamawaki, Ichiro,Ueda, Shuichi,Matsumoto, Hiroshi,Matsuura, Naosuke,Yasumoto, Mitsugi,Koda, Akihide,Hori, Mikio
p. 3330 - 3336
(2007/10/03)
SYNTHESIS OF 5,1-BENZOTHIAZOCINES AND THEIR HOMOLOGUES
A facile one pot synthesis of 1,5-benzothiazocines and their homologues from acyclic aniline derivatives has been achieved by the effective synthetic control via aza-sulfonium intermediates.