Synthesis of Substituted Thioamides from <i>gem</i>‐Dibromoalkenes and Sodiumsulfide

Morri, Ashok K.; Thummala, Yadagiri; Adepu, Ramesh; Sharma, G. V. M.; Ghosh, Subhash; Doddi, Venkata Ramana

doi:10.1002/ejoc.201901411

Cited by 3 publications

(1 citation statement)

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“…Na 2 S-mediated synthesis of 2-arylethanethioamides in DMF by Jiang and co-workers [61]. Doddi and co-workers used sodium sulfide and N-substituted formamide in a threecomponent transformation of gem-dibromostyrenes (Scheme 39) [62]. A series of 2-arylethanethioamides 96 were obtained in fair-to-excellent yields in the absence of any catalyst.…”

Section: Sodium Sulfide As a Sulfuration Agentmentioning

confidence: 99%

Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update

2023

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Compounds possessing a thioamide function play a crucial role in organic synthesis, serving as key building blocks. They are also important in the pharmaceutical chemistry and drug design, owing to their ability to mimic the amide function in biomolecules while retaining or developing biological activity. From the synthetic viewpoint, several methods have been developed for preparing thioamides using sulfuration agents. The purpose of this review is to give an update of the last decade of contributions focusing on the formation of thioamides employing different sulfur sources. When appropriate, the cleanness and practicality of the new methods are highlighted.

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Section: Sodium Sulfide As a Sulfuration Agentmentioning

confidence: 99%

Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update

2023

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Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur

et al. 2020

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A mild and chemoselective method for the thioacylation of amines using -ketoacids and elemental sulfur has been developed. The key to success for this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties are tolerated under the applied reaction conditions. To demonstrate the advantages of this method compared to conventional O-S exchange reactions using Lawesson's reagent or P2S5, thioamide moieties were introduced sitespecifically into biologically active compounds.

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