Dithiocarbamate-mediated thioamidation of arylglyoxylic acids by decarboxylative–decarbonylative C–C bond formation reactions

Abstract

Arylglyoxylic acids have been employed in a novel decarboxylative-decarbonylative thioamidation reaction with the dithiocarbamate intermediates prepared in situ by the prompt reaction of amines and carbon disulfide. A series of...

Dithiocarbamate mediated thioamidation via C–C single bond cleavage of styrene: study of the protocol in decarbonylative and decarboxylative thioamidations

“…Formation of the PhCO˙ radical intermediate has been proved by trapping it with TEMPO (Scheme 3a, k and n). The PhCO˙ radical undergoes decarbonylation 3,7 b ,14 to generate the Ph˙ radical intermediate. However, benzoic acid follows a decarboxylative pathway to generate the Ph˙ radical in the presence of persulfate 15 via the formation of the carboxyphenyl radical intermediate (PhCOO˙).…”

“…2 Our group has recently reported decarboxylative-decarbonylative thioamidation of arylglyoxylic acids using dithiocarbamates as the source of the thioamide group (Scheme 1a). 3 We have explored dithiocarbamates as the reaction intermediates for preparing various useful organosulfur compounds. 4 As a continuation of our work we report here a dealkenylative approach for the synthesis of thioamides from styrene using freshly prepared dithiocarbamate salts.…”

Metal-free trifunctionalization of phenylacetylenes: an efficient one-pot two-step synthesis ofgem-bis(dithiocarbamates)

“…In our previous report, we demonstrated the β-dithiocarbamylation of styrenes. 7 As a continuation of our research work involving the dithiocarbamate chemistry, 8 here we are introducing a novel strategy to obtain phenacyl-bis(dithiocarbamates) by molecular bromine-mediated trifunctionalization of phenylacetylenes (Scheme 1).…”

Base-mediated synthesis of cyclic dithiocarbamates from 1-amino-3-chloropropan-2-ol derivatives and carbon disulfide

“…Due to their extensive biological applications in medicinal and agricultural chemistry, dithiocarbamates are considered to be an important class of molecules. 1,2 Thus, a number of procedures have been developed for the preparation of dithiocarbamates. 3–6 One simple synthetic method is a three-component reaction of primary/secondary amines, CS 2 , and electrophiles such as alkyl halides through dithiocarbamic acid salt intermediates (Scheme 1a).…”