New Synthesis of Dimethyl‐cinnamoylimino‐dithiocarboxylate and Reactions with Nucleophiles
A new general synthesis of dimethyl‐cinnamoylimino‐dithiocarboxylate 1d is possible by reaction of 4‐nitro‐cinnamoylamide with carbon disulfide in the presence of sodium hydride and following alkylation. With the unsubstituted dimethyl‐cinnamoylimino‐dithiocarboxylate 10 is in‐vestigated the reaction behavior with nucleophilic compounds. The treatment of 1c with primary amines, respectively, by mono‐ and disubstitution of the methylthio groups yields isothiourea 2 or guanidines 3. Benzocondensed heterocycles are formed by reaction of 1c with o‐bifunctional nucleo‐philes.
The compounds 5, 6 and 7 have been synthesized from 1c with cysteamine, p‐phenylenediamine and ethylenediamine.
The oxadiazole 8 and isothiosemicarbazide 9 are obtained by reaction of the dithioester 1c with hydrazides. On the other hand cyclisation to the 1,2,4‐triazole 11 over the intermediate 10 and to the 1,3,5‐triazine 12 are possible.
The reaction of 1c with carbanions in a basic medium affords acrylic derivatives 13.
In the same way we isolated by reaction of dithioester 1c with a benzothiazolium salt the dark coloured compound 14. The physical properties of synthesized compounds are discussed by mass‐, ^1^H‐n.m.r.‐, i.r.‐ and u.v.‐spectra.