3-(4-Thiocarbamoyl-1,2,3-triazol-1-yl)benzo-15-crown-5: synthesis and properties

Prokhorova, P. E.; Глухарева, Т. В.; Dyudya, L. V.; Алексеева, Е. А.; Morzherin, Yu. Yu.

doi:10.1007/s11172-010-0177-1

Cited by 5 publications

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“…Thus thiadiazoles 48 undergo Dimroth-type rearrangement to form 1H-1,2,3-triazol-3-ium-5-thiolates 49, in good yields[34]. 4-Carbimino-1,2,3-thiadiazoles 48 (R 3 = HC = NR) formed by reaction of 4-formyl-1,2,3-thiadiazole with amines, are labile and rearrange to 1,2,3-triazol-4-carbothioamides 50 under the conditions used for their generation[39,40]. It was found that interaction of 1,2,3-thiadiazolylhydrazones of acetophenones with phosphorus pentachloride in benzene or toluene leads to 5H-[1,2,3]triazolo[5,1-b][1,3,4] thiadiazines 51.…”

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Progress in intermolecular and intramolecular reactions of thioamides with diazo compounds and azides

Бакулев

Shafran

Dehaen

2019

Tetrahedron Letters

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Reactions of thioamides with nitrogen-rich 1,3-dipoles, diazo compounds and azides, have been known for long time already. However in recent years introduction of catalysts of different types (rhodium-, ruthenium-and copper-containing and Lewis acids) as well as highly electrophilic sulfonyl azides, allowed the development of new methods for the synthesis of heterocycles, enamines and N-sulfonyl amidines. Moreover, a new methodology in organic synthesis, based on generation and subsequent transformations of a-diazocarbonyl compounds was created. Reactions of sulfonyl azides with thioamides undergo readily in mild conditions to produce different sorts of N-sulfonyl amidines and represent a new type of click-type processes. Most of the cited works were published in the current decade. Earlier seminal papers are also reviewed when they constitute the background for new synthetic methods which were developed further.

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