ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
New Synthesis of Dimethyl-cinnamoylimino-dithiocarboxylate and Reactions with NucleophilesA 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-, 1H-n.m.r.-, i.r.- and u.v.-spectra.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19803220314
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