Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/111996
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.
Mazur, D.
Beliaev, N. A.
Volkova, N. N.
Ilkin, V. G.
Dehaen, W.
Lebedev, A. T.
Bakulev, V. A.
Issue Date: 2019
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.
Keywords: AROMATIC COMPOUNDS
CHLORINE COMPOUNDS
SODIUM AZIDE
1 ,2 ,3-TRIAZOLES
AROMATIC AZIDES
ATOM ECONOMIC
ECO-FRIENDLY
ONE-POT REACTION
ROLE OF WATER
SULFONYL AZIDES
SULFONYL CHLORIDES
ENVIRONMENTAL PROTECTION
1,2,3 TRIAZOLE DERIVATIVE
ALKALI
AZIDE
CHLORIDE
SODIUM AZIDE
THIADIAZOLE DERIVATIVE
THIOACETAMIDE DERIVATIVE
WATER
ARTICLE
CATALYST
CHEMICAL REACTION
ONE POT SYNTHESIS
SYNTHESIS
URI: http://hdl.handle.net/10995/111996
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85073120953
PURE ID: 11333124
ISSN: 0022-3263
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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