jo5b02497_si_001.pdf (5.9 MB)
The Reaction of DABCO with 4‑Chloro‑5H‑1,2,3-dithiazoles: Synthesis and Chemistry of 4‑[N‑(2-Chloroethyl)piperazin-1-yl]‑5H‑1,2,3-dithiazoles
journal contribution
posted on 2016-01-15, 00:00 authored by Maria Koyioni, Maria Manoli, Panayiotis A. KoutentisN-(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)anilines
react with DABCO in hot PhCl to give N-{4-[N-(2-chloroethyl)piperazin-1-yl]-5H-1,2,3-dithiazol-5-ylidene}anilines in high yields (70–92%).
The reaction also works with 4-chloro-5H-1,2,3-dithiazol-5-one
and -thione, giving the corresponding products in 85% and 76% yields,
respectively. While the reaction of several (4-chloro-5H-1,2,3-dithiazol-5-ylidene)methanes with DABCO failed to give
{4-[N-(2-chloroethyl)piperazin-1-yl]-5H-1,2,3-dithiazol-5-ylidene}methanes, these can be
prepared in moderate yields via classical cycloaddition–retrocycloaddition
strategies from 4-[N-(2-chloroethyl)piperazin-1-yl]-5H-1,2,3-dithiazole-5-thione. The 2-chloroethyl moiety on
selected dithiazoles was also modified without cleavage of the 1,2,3-dithiazole
by reaction with various nucleophiles, giving access to 4-[N-(2-substituted)piperazin-1-yl]-5H-1,2,3-dithiazoles in moderate to high yields.