Synthesis and Spectroscopic Characterization of Arylated Selenoureas

Pfeiffer, W.‐D.; Ahlers, Klaus‐Dieter; Falodun, Abiodun; Villinger, Alexander; Langer, Peter

doi:10.1080/10426507.2013.820729

Cited by 8 publications

(3 citation statements)

References 17 publications

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“…We reinvestigated this work and prepared selenoureas 17a-l by reaction of anilines with isoselenocyanates 16a-l which were obtained by reaction of isonitriles 15a-l with selenium (Scheme 12). 18 Scheme 12 Synthesis of 17a-l 4-Aryl-2-imino-2H-selenazolines can be formally regarded as N-substituted 2-amino-1,3-selenazoles. We have developed a synthesis of 4-aryl-2-imino-2H-selenazolines 20a-f, albeit in low isolated yields, by cyclization of anilines 19a-c with -(selenocyanato)acetophenones 18a-d which were prepared by reaction of the corresponding phenacyl bromides with KSeCN (Scheme 13).…”

Section: Scheme 11 Synthesis Of 14mentioning

confidence: 99%

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Adventures in 1,3-Selenazole Chemistry

Langer

2021

Synlett

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The synthesis of 1,3-selenazoles and related compounds, including 2,4,5-trisubstituted, 2,4-disubstituted, 4,5-disubstituted, 4-substituted 1,3-selenazoles, and parent unsubstituted 1,3-selenazole, is highlighted. Emphasis is also given on 2-benzoyl-1,3-selenazoles which can be functionalized by Knoevenagel reactions or by rearrangements via their corresponding oximes. Syntheses of bis-, tris-, and tetrakis(1,3-selenazoles) are discussed as well. 1,3,4-6H-Selenadiazines are available from selenosemicarbazides and can undergo ring-contraction or deselenation reactions. Most syntheses rely on the application of selenocarboxylic amides, selenourea and related building blocks which are conveniently available by reaction of the corresponding oxygen analogues with P4Se10.1 Introduction2 Selenocarboxylic Amides3 2,4,5-Tri- and 2,4-Disubstituted 1,3-Selenazoles4 Bis(1,3-selenazoles)5 2-Amino-1,3-selenazoles6 2-Unsubstituted 1,3-Selenazoles7 1,3,4-Selenadiazines8 Conclusions

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Section: Scheme 11 Synthesis Of 14mentioning

confidence: 99%

“…We reinvestigated this work and prepared selenoureas 17a – l by reaction of anilines with isoselenocyanates 16a – l which were obtained by reaction of isonitriles 15a – l with selenium (Scheme 12 ). 18…”

Section: -Amino-13-selenazolesmentioning

confidence: 99%

Adventures in 1,3-Selenazole Chemistry

Langer

2021

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“…Selenourea derivatives were synthesized from the following starting compounds—sources of selenium: isoselenocyanates and primary or secondary amines [27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44] selenoamides and nitrile oxides (generated in situ) [45], hydrogen selenide [46,47,48], lithium aluminum hydride (LiAlH 2 Se) [12,32,36,49,50,51,52,53], bis(dimethylaluminum) selenide [54], tetraethylammonium tetraselenotungstate [14], elemental selenium with an isonitrile and an amine [55], elemental selenium with an amine and triethylorthoformate [56], and elemental selenium with a secondary amine, a base, and dihalomethan derivatives [57,58].…”

Section: Introductionmentioning

confidence: 99%

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

et al. 2019

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The reactions of 3-isoselenocyanato-2,2,5,5-tetramethylpyrrolidine-1-oxyl, 3-isoselenocyanatomethyl-2,2,5,5-tetramethyl-3-pyrrolidine-1-oxyl, and 4-isoselenocyanato-2,2,6,6-tetramethylpiperidine-1-oxyl with selected amines and alcohols give the corresponding novel nitroxyl selenoureas and selenocarbamates, all bearing a nitroxyl moiety. Synthesized selenoureas and selenocarbamates show significant activity against pathogenic fungi and bacteria. In contrast to piperidine nitroxides, pyrrolidine, five-membered nitroxyl selenoureas and selenocarbamates show excellent antifungal and antibacterial activity against pathogenic fungi and bacteria, respectively.

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Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

et al. 2020

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Herein, we report a non‐metal strategy for cyclization reactions of 2‐vinylanilines with/without isonitriles to synthesize 2‐aminoquinoline and 3‐aryl‐1H‐indole derivatives. A series of 2‐aminoquinolines were afforded in good to excellent yields in a direct, facile, and efficient approach by Se‐catalyzed isocyanide insertion with 2‐vinylanilines under an air atmosphere. This reaction not only used low toxicity Se as the catalyst, isocyanobenzene substrates were compatible too compared to previous report. Meanwhile, an intramolecular cyclization of 2‐vinylanilines was developed to give 3‐aryl‐1H‐indoles in moderate to good yields by using SeO2 as oxidant.

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Synthesis and Spectroscopic Characterization of Arylated Selenoureas

Cited by 8 publications

References 17 publications

Adventures in 1,3-Selenazole Chemistry

Adventures in 1,3-Selenazole Chemistry

Reactions of Nitroxides, Part 17. Synthesis, Fungistatic and Bacteriostatic Activity of Novel Five- and Six-Membered Nitroxyl Selenoureas and Selenocarbamates

Selenium‐Mediated Cyclization Reaction of 2‐Vinylanilines with/without Isonitriles: Efficient Synthesis of 2‐Aminoquinoline/ 3‐Aryl‐1H‐indole Derivatives

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