Water/Alkali-Catalyzed Reactions of Azides with 2-Cyanothioacetamides. Eco-Friendly Synthesis of Monocyclic and Bicyclic 1,2,3-Thiadiazole-4-carbimidamides and 5-Amino-1,2,3-triazole-4-carbothioamides.

Clicks: 293
ID: 58327
2019
Article Quality & Performance Metrics
Overall Quality
Not rated
Combines reader engagement with the AI quality analysis. This article has not been analysed, so there is no overall score — reader engagement is measured and shown alongside.
AI Quality Assessment
Not analyzed
Readership in this journal
Steady

Ranked #32 of 103 articles by views in The Journal of organic chemistry

Most read Least read

Bar heights use a square-root scale.

Mint this article as an NFT
Not yet minted

Create a permanent, verifiable on-chain record of this article on the Scimatic Network. The NFT is held in your Journament account, and you can withdraw it to your own wallet at any time.

5 SUSD one-off · no wallet required
Sign in to mint
Abstract
The reactions of thioamides with azides in water were studied. It was reliably shown that the reaction of 2-cyanothioacetamides with various types of azides in water in the presence of alkali presents an efficient, general, one-step, atom-economic, and eco-friendly method for the synthesis of 1,2,3-thiadiazol-4-carbimidamides and 1,2,3-triazole-4-carbothioamides . This method can be extended to the one-pot reaction of sulfonyl chlorides and 6-chloropyrimidines with sodium azide, leading to final products in higher yields, that is, avoiding the isolation of unsafe sulfonyl azides. The method was furthermore applied to the reaction of ,'-bis-(2-cyanothiocarbonyl)pyrazine with sulfonyl azides to afford bicyclic 1,2,3-thiadiazoles and 1,2,3-triazoles connected via a 1,1'-piperazinyl linker. 2-Cyanothioacetamides were also shown to react with aromatic azides in water in the presence of alkali to afford 1-aryl-5-amino-1,2,3-triazole-4-carbothioamides . In contrast to aromatic azides and similarly to sulfonyl azides, 6-azidopyrimidine-2,4-diones react with cyanothioacetamides to form -pyrimidin-6-yl-5-dialkylamino-1,2,3-thiadiazole-4--l-carbimidamides . A mechanism was proposed to rationalize the role of water in changing the reactivity of azides toward 2-cyanothioacetamides.
Reference Key
filimonov2019wateralkalicatalyzedthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Filimonov, Valeriy O;Dianova, Lidia N;Beryozkina, Tetyana V;Mazur, Dmitrii;Beliaev, Nikolai A;Volkova, Natalia N;Ilkin, Vladimir G;Dehaen, Wim;Lebedev, Albert T;Bakulev, Vasiliy A;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b01599
URL
Keywords
1,2,4-triazoles 2,2,2-trifluoro acetimidoyl chloride amidine oxidative cyclization

Citations

No citations found. To add a citation, contact the admin at info@scimatic.org

Comments

No comments yet. Be the first to comment on this article.