Synthesis of sugar-derived isoselenocyanates, selenoureas, and selenazoles

López, Óscar; Maza, Susana; Ulgar, Vı́ctor; Maya, Inés; Fernández-Bolaños, José G.

doi:10.1016/j.tet.2009.01.038

Cited by 59 publications

(44 citation statements)

References 63 publications

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“…Reaction of phenyl isoselenocyanate [18] with -glucosamine hydrochloride in aqueous ethanol in the presence of NaHCO 3 afforded 5-hydroxy-4-polyhydroxyalkylimidazolidine-2-selone 3 in a high yield of 99 % after column chromatography (Scheme 1). This reaction must be carried out in the dark, as many selenium-containing compounds undergo UV-induced decomposition.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

et al. 2009

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We report the synthesis of acyclic and spiranic imidazole-derived C-selenonucleosides. 5-Hydroxy-4-tetrahydroxybutyl imidazolidine-2-selones, a novel class of acyclic selenonucleosides, were transformed into (tetrahydroxybutylimidazol-2-yl)diselenide, by acetylation and chemoselective N-deacetylation with methanolic imidazole. Furthermore, the synthesis of a new class of conformationally restricted arabinoconfigured spironucleosides containing an imidazolidine-2-

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Section: Resultsmentioning

confidence: 99%

“…We have devoted our efforts in developing strategies to reach, from carbohydrates, stable and versatile organoselenium templates. [18] In this communication we have…”

Section: Introductionmentioning

confidence: 86%

Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

et al. 2009

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“…In recent time, various efficient procedures for their preparation have been developed. One of the most efficient and convenient procedure for the synthesis of selenoureas 1 in high yield is based on the reaction of aryl and alkyl isoselenocyanates 2 with various primary and secondary amines [61][62][63][64][65][66][67][68][69][70]. N-Acyl selenoureas 5 can be obtained by reaction of amines with acyl isoselenocyanates 4 which are prepared in turn from acyl chlorides 3 and potassium selenocyanate [68,[71][72][73][74] (Scheme 1).…”

Section: Synthesis Of Selenoureasmentioning

confidence: 99%

“…The first step of this reaction is alkylation of 14 at the selenium atom to give isoselenourea 28 which undergoes cyclization to 4,5-dihydro-1,3-selenazol-4-ol 29, and dehydration of the latter yields 1,3-selenazole 30 (Scheme 8) [92]. Although N,N-disubstituted N′-acylselenoureas 5 were reported previously [68,[71][72][73], they were not involved in the synthesis of 1,3-selenazoles according to the classical Hantzsch reaction until it was modified [92,98].…”

Section: Selenium-containing Heterocyclesmentioning

confidence: 99%

Synthesis of selenoureas and heterocycles based thereon

et al. 2015

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“…It is also well documented that many seleninum-containing products display diverse biological activities, and some are of significant importance in the pharmaceutical and agrochemical fields [2]. In analogy to isocyanates and isothiocyanates, isoselenocyanates easily react with N-nucleophiles, such as primary and secondary amines, furnishing the corresponding selenoureas [1] [3]. Hydrazines display a similar reactivity leading to selenosemicarbazides [4].…”

Section: Introduction -Isoselenocyanates Are Well Known As Versatilementioning

confidence: 99%

New Selenosemicarbazides Derived from Imidazole‐Based Carbohydrazides

Pieczonka

Ciepielowski

Cebulska

et al. 2013

Helvetica Chimica Acta

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Imidazole-based carbohydrazides, i.e., 3-oxidoimidazole-4-carbohydrazides 1 and 2-[(imidazol-2-yl)sulfanyl]acetohydrazides 6, react with aryl isoselenocyanates 4 in MeOH at room temperature to give the corresponding selenosemicarbazides 5 and 7, respectively, in good yields. On heating 7b in DMF in the presence of air to 100°, 1,3,4-oxadiazole 8a was formed via cyclization and formal elimination of H2Se. Product 8a was also obtained after heating of a mixture of 4a and 6b under the same conditions. On the other hand, on heating of a solution of 7c in MeOH at reflux, a cyclization occurred to give the corresponding 1,2,4-triazole-3-selone 9b. Again, the same product was formed when a mixture of 4b and 6b was heated in MeOH. Surprisingly, analogous cyclizations of selenosemicarbazides of type 5 under the same conditions failed, and only decomposition was observed. The structures of 7a, 7d, and 9b have been established by X-ray crystallography. and 2-(imidazol-2-yl)sulfanylacetohydrazides 6, react with aryl isoselenocyanates 4 in MeOH at room temperature to give the corresponding selenosemicarbazides 5 and 7, respectively, in good yields. On heating 7b in DMF in the presence of air to 100°, 1,3,4-oxadiazole 8a was formed via cyclization and formal elimination of H 2 Se. Product 8a was also obtained after heating of a mixture of 4a and 6b under the same conditions. On the other hand, on heating of a solution of 7c in MeOH at reflux, a cyclization to give the corresponding 1,2,4-triazole-3-selone 9b occurred. Again, the same product was formed when a mixture of 4b and 6b was heated in MeOH. Surprisingly, analogous cyclizations of selenosemicarbazides of type 5 under the same conditions failed, and only decomposition was observed. The structures of 7a, 7d, and 9b have been established by X-ray crystallography.

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Synthesis of sugar-derived isoselenocyanates, selenoureas, and selenazoles

Cited by 59 publications

References 63 publications

Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

Synthesis of selenoureas and heterocycles based thereon

New Selenosemicarbazides Derived from Imidazole‐Based Carbohydrazides

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