Novel Synthesis of cis-Nickel(II) 3-Alkylimino-3-alkyl(or aryl)thio-1-arylpropenethiolates and Their Application to the Preparation of 5-Aryl-3-(arylthio)isothiazoles

Abstract

Treatment of (E)-3-alkylamino-3-alkylthio-1-(thioaroyl)propenes 2 with Ni(OAc)2.4H2O in EtOH at room temperature gave cis-Ni(II)-3-alkylimino-3-alkylthio-1-arylpropenethiolates 3 in excellent yields. Heating a mixture of 3 and alkyl- or arylthiols in 1,2-dichloroethane gave new ketene S,N-acetals 4 having new alkyl- or arylthio groups depending on the thiols employed. For the first time, 5-aryl-3-(arylthio)isothiazoles were prepared from 2 with an arylthio group according to a known procedure.

Five‐Membered Heterocycles: 1,2‐Azoles. Part 2. Isoxazoles and Isothiazoles

“…Dealkylation with KI in DMSO affords the corresponding 5-aryl-3-(arylthio)isoxazoles 106 (Scheme 9.34) [200].…”

“…2-Alkyl-3-alkylthio-5-arylisothiazolium halides 289 are reduced to the S,N-acetals 290 by treatment with NaBH 4 in ethanol at room temperature (Scheme 9.121) [200,371]. [214].…”