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|Title:||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|
|Authors:||Filimonov, V. O.|
Dianova, L. N.
Beryozkina, T. V.
Beliaev, N. A.
Volkova, N. N.
Ilkin, V. G.
Lebedev, A. T.
Bakulev, V. A.
|Publisher:||American Chemical Society|
American Chemical Society (ACS)
|Citation:||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 / V. O. Filimonov, L. N. Dianova, T. V. Beryozkina et al. // Journal of Organic Chemistry. — 2019. — Vol. 84. — Iss. 21. — P. 13430-13446.|
|Abstract:||The reactions of thioamides with azides in water were studied. It was reliably shown that the reaction of 2-cyanothioacetamides 1 with various types of azides 2 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 5 and 1,2,3-triazole-4-carbothioamides 4. This method can be extended to the one-pot reaction of sulfonyl chlorides and 6-chloropyrimidines 2′o 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 N,N′-bis-(2-cyanothiocarbonyl)pyrazine 1h with sulfonyl azides to afford bicyclic 1,2,3-thiadiazoles 8 and 1,2,3-triazoles 9 connected via a 1,1′-piperazinyl linker. 2-Cyanothioacetamides 1 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 11. In contrast to aromatic azides and similarly to sulfonyl azides, 6-azidopyrimidine-2,4-diones 2o-q react with cyanothioacetamides to form N-pyrimidin-6-yl-5-dialkylamino-1,2,3-thiadiazole-4-N-l-carbimidamides 12. A mechanism was proposed to rationalize the role of water in changing the reactivity of azides toward 2-cyanothioacetamides. Copyright © 2019 American Chemical Society.|
1 ,2 ,3-TRIAZOLES
ROLE OF WATER
1,2,3 TRIAZOLE DERIVATIVE
ONE POT SYNTHESIS
|metadata.dc.description.sponsorship:||We gratefully acknowledge financial support of this work by the Russian Science Foundation (18-13-00161).|
|RSCF project card:||18-13-00161|
|Appears in Collections:||Научные публикации, проиндексированные в SCOPUS и WoS CC|
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