Abstract
Diaroyl sulfides were prepared in one-pot reaction from ethylenediamine and carbon disulfide, via reaction of in situ generated ethylene-bis-carbamodithioates with aroyl chlorides. The reaction of diaroyl sulfides with acetylenic and ethylenic π-deficient compounds such as dimethyl acetylenedicarboxylate, ethyl propiolate, (E)-1,4-diphenylbut-2-ene-1,4-dione and 1,4diphenylbut-2-yne-1,4-dione afforded the corresponding thionylated products. NMR spectroscopic data of the isolated products were discussed.
Highlights
Diaroyl sulfides were previously described in the literature[1] and their synthesis remains of interest due to their biological importance.[2]
The bis(dithiocarbamate) salt 110 was synthesized by adding carbon disulfide to a solution of ethylenediamine and triethylamine as outlined in Scheme 1
It was reported that the reaction of polymethylene diamines with aroyl chloride and ammonium thiocyanate under solid-liquid phase-transfer catalysis by polyethylene glycol-400 (PEG-400) yielded polymethylene-bis-aroyl thioureas in good-to-excellent yields.[11]
Summary
Diaroyl sulfides were previously described in the literature[1] and their synthesis remains of interest due to their biological importance.[2]. Reaction of two equivalents of diaroyl sulfides 2a-c1a with one equivalent of dimethyl acetylenedicarboxylate (7) gave mainly 2,3-dimethyl bis(aroylthio)succinates 8a-c in good yields (Scheme 3). The reaction afforded ethyl (2Z)-3(benzoylthio)acrylates 12a-c (Scheme 5).
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
