Synthesis of Dithiocarbamates by Markovnikov Addition Reaction in PEG and Their Application in Amidoalkylation of Naphthols and Indoles

Abstract

Synthesis of dithiocarbamates by the one-pot three-component Markovnikov addition reaction of an amine, carbon disulfide and an alkyl vinyl ether or N -vinylpyrrolidone is reported in polyethylene glycol (PEG) under a mild and green procedure with high yields and completely regiospecific. Also, the products were used as efficient starting materials for amidoalkylation of electron-rich arenes such as naphthols and indoles. ]]>

Organotin(IV) Dithiocarbamate Complexes: Chemistry and Biological Activity

“…They have found other usage in agriculture as pesticides, herbicides, and fungicides [ 37 , 38 , 39 ]. Some compounds of these classes have been commercialized such as zineb, maneb, nabam, ziram and ferbam [ 40 ].…”

“…The earliest synthetic record of dithiocarbamate synthesis involved the use of thiophosgene, chlorothioformate and an isothiocyanate [ 40 ]. This had many drawbacks such as long reaction time, use of expensive and toxic reagents, and harsh reaction conditions.…”

“…This had many drawbacks such as long reaction time, use of expensive and toxic reagents, and harsh reaction conditions. Several synthetic procedures have been developed involving one-pot condensation of amines, carbon disulfide and electrophiles such as alkyl halides, epoxides, carbonyl compounds and α,β-unsaturated compounds [ 40 ]. They have been prepared from both the primary and secondary amine [ 32 , 41 , 42 ] as shown in Scheme 1 .…”

“…However, organotin(IV) dithiocarbamate complexes have been mostly reported to be prepared in situ. The in situ method involves a one pot system in which the organotin(IV) compound is introduced into the flask containing freshly prepared dithiocarbamate, and allowed to react for a few hours [ 40 ]. Some organotin(IV) dithiocarbamate complexes prepared via this method have been reported.…”

Transition-Metal-Free Coupling Reaction of Dithiocarbamates with Indoles: C–S Bond Formation

“…The chemistry of dithiocarbamates is well-known for their widespread applications in agriculture, polymer chemistry, and coordination chemistry . Recently, dithiocarbamates have been used as intermediates in synthetic organic chemistry for the construction of biologically active compounds . Various heterocyclic compounds containing dithiocarbamate groups including chromone-dithiocarbamate, triazole-dithiocarbamates, benzodioxole-dithiocarbamates, benzimidazole-dithiocarbamates, indole-dithiocarbamates, and quinazolinone-dithiocarbamate have been introduced as potential anticancer agents .…”