10.1021/acs.joc.5b02497.s001

The Reaction of DABCO with 4‑Chloro‑5<i>H</i>‑1,2,3-dithiazoles: Synthesis and Chemistry of 4‑[<i>N</i>‑(2-Chloroethyl)piperazin-1-yl]‑5<i>H</i>‑1,2,3-dithiazoles

Abstract

<i>N</i>-(4-Chloro-5<i>H</i>-1,2,3-dithiazol-5-ylidene)­anilines react with DABCO in hot PhCl to give <i>N</i>-{4-[<i>N</i>-(2-chloroethyl)­piperazin-1-yl]-5<i>H</i>-1,2,3-dithiazol-5-ylidene}­anilines in high yields (70–92%). The reaction also works with 4-chloro-5<i>H</i>-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-5<i>H</i>-1,2,3-dithiazol-5-ylidene)­methanes with DABCO failed to give {4-[<i>N</i>-(2-chloroethyl)­piperazin-1-yl]-5<i>H</i>-1,2,3-dithiazol-5-ylidene}­methanes, these can be prepared in moderate yields via classical cycloaddition–retrocycloaddition strategies from 4-[<i>N</i>-(2-chloroethyl)­piperazin-1-yl]-5<i>H</i>-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-[<i>N</i>-(2-substituted)­piperazin-1-yl]-5<i>H</i>-1,2,3-dithiazoles in moderate to high yields

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oai:figshare.com:article/2087386Last time updated on 2/12/2018

This paper was published in FigShare.

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