A novel approach to a substituted 1,3-selenazole core as a precursor of electron rich olefins: diselenadiazafulvalene and azino-diselenadiazafulvalene

Časar, Zdenko; Maréchal, Alenka Majcen-Le; Lorcy, Dominique

doi:10.1039/b302942p

Cited by 21 publications

(3 citation statements)

References 25 publications

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“…Although the generality of these processes have not yet been fully explored, reaction of ester 5b with the carbanions generated from 50 are utilized to prepare selenazoles 51 and 52 (Scheme 25). 31 The use of t-BuOK as a base leads to formation of trisubstituted selenazoles 51. Although the yields of 51 are low, this substance cannot be easily formed by using other methods.…”

Section: Scheme 24mentioning

confidence: 99%

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Murai¹

2005

Synlett

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This review describes the synthesis and reactions of selenothioic acid S-esters and diselenoic acid esters. Synthetic work with these substances has provided observations, which have led to a proposal about factors that effect their stability. A survey shows that aliphatic derivatives of selenothioic acid S-esters, although being stable compounds, are highly reactive with various electrophilic and nucleophilic reagents. In addition, a-protons in these esters have high acidities. Studies have shown that the chemistry of these esters can be utilized in the synthesis of new types of organoselenium compounds.

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Section: Scheme 24mentioning

confidence: 99%

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Murai¹

2005

Synlett

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“…Selenazoles have been extensively described as useful synthetic tools [ 1 , 2 , 3 , 4 ] with biologically significant antibiotic [ 5 ] and cancerostatic [ 6 , 7 ] and superoxide anion scavenging activity [ 8 ]. A few reports have appeared on the synthesis of selenazoles and thiazoles, including both solid phase [ 9 ] and solution phase synthesis [ 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Single Crystal Structures of Substituted-1,3-Selenazol-2-amines

Hua

Slawin

et al. 2016

Molecules

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The synthesis and X-ray single crystal structures of a series of new 4-substituted-1,3-selenazol-2-amines is reported. The efficient preparation of these compounds was carried out by two-component cyclization of the selenoureas with equimolar amounts of α-haloketones. The selenoureas were obtained from the reaction of Woollins’ reagent with cyanamides, followed by hydrolysis with water. All new compounds have been characterized by IR spectroscopy, multi-NMR (1H, 13C, 77Se) spectroscopy, accurate mass measurement and single crystal X-ray structure analysis.

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“…Several reviews [1] describe their preparation [2] and pharmaceutical potential [3]. They have been studied widely, for example as anticancer [4] and antiradiation agents [5], as protein kinase activators [6] and as superoxide anion-scavengers [7], but they are also well recognized in dye chemistry [8] and with respect to their physical properties [9].…”

mentioning

confidence: 99%

Selenium‐Containing Heterocycles from Isoselenocyanates: 4‐Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride

Sommen¹,

Linden²,

Heimgartner³

2008

Helvetica Chimica Acta

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Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et3N to give the corresponding 2‐(3‐aryl‐2,3‐dihydro‐4‐methyl‐1,3‐selenazol‐2‐ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6f) instead of 6a. In some cases, the corresponding noncyclic 2‐[(arylamino)(prop‐2‐ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X‐ray crystallography.

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A novel approach to a substituted 1,3-selenazole core as a precursor of electron rich olefins: diselenadiazafulvalene and azino-diselenadiazafulvalene

Cited by 21 publications

References 25 publications

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Synthesis and Reactions of Selenothioic Acid S-Esters and Diselenoic Acid Esters

Synthesis and Single Crystal Structures of Substituted-1,3-Selenazol-2-amines

Selenium‐Containing Heterocycles from Isoselenocyanates: 4‐Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride

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