Synthese und IR‐Spektren von Aryl‐isoselenocyanaten

Bulka, Ehrenfried; Ahlers, Klaus‐Dieter; Tuček, E.

doi:10.1002/cber.19671000439

Cited by 35 publications

(10 citation statements)

References 12 publications

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“…Arylisocyanide reagieren mit elementarem Selen unter Bildung von Isoselenocyanaten 120. Wenig später wurden analoge Reaktionen mit Alkylisocyaniden in Gegenwart einer Base und die anschließenden Umsetzungen der so gebildeten Isoselenocyanate mit Aminen und Alkoholen zu Selenoharnstoffen 232 a bzw.…”

Section: Additionen An Die Isocyanogruppe Mit Anschließender Cycliunclassified

Isocyanide in der Synthese von Stickstoff‐Heterocyclen

2010

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Isocyanide bewähren sich seit langem als unersetzliche Bausteine in der modernen organischen Chemie. Die einzigartigen Eigenschaften der Isocyanogruppe machen Isocyanide für die Synthese etlicher wichtiger Klassen von Stickstoff‐Heterocyclen wie Pyrrolen, Indolen oder Chinolinen besonders wertvoll. In letzter Zeit wurde eine ganze Reihe von Cocyclisierungen von Isocyaniden über Zwitterionen und radikalische Intermediate ebenso wie übergangsmetallkatalysierte Synthesen verschiedener Arten von Heterocyclen entwickelt. Methoden, die von Isocyaniden ausgehen, weisen oftmals deutliche Vorteile gegenüber alternativen Wegen auf, was oft der verbesserten Konvergenz und der Einfachheit solcher Verfahren sowie der großen Vielfalt einfach zugänglicher Isocyanide geschuldet ist. So finden Isocyanide auch in enantioselektiven Synthesen chiraler heterocyclischer Verbindungen einschließlich Naturstoffen Verwendung.

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Section: Additionen An Die Isocyanogruppe Mit Anschließender Cycliunclassified

Isocyanide in der Synthese von Stickstoff‐Heterocyclen

2010

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“…The direct addition of selenium to isocyanides using black, finely powdered, elemental selenium in an organic solvent is the most typical method for the synthesis of isoselenocyanates. 9,10,[34][35][36][37][38][39][40][41] In our previous research, we have obtained isoselenocyanates (bearing nitroxyl 25 and aryl 26 moieties) from isocyanides. Unfortunately, we observed unreproducible results when the addition of selenium to isocyanides with black, finely powdered, elemental selenium occurred either in chloroform or in tetrahydrofuran in the presence of triethylamine (see below).…”

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confidence: 99%

Synthesis of Isoselenocyanates

2015

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“…39 While this method does provide moderate to high yields while using inexpensive elemental selenium, major disadvantages are the varied toxicities and extremely pungent odor of isocyanide molecules. 40,41 ISCs have also been synthesized by using a primary amine, CSe2 and HgCl2 in the presence of triethylamine (Figure 2-2). 42 This method attempts to stray away from isocyanides.…”

Section: Preparation Of Isoselenocyanates (Iscs)mentioning

confidence: 99%

Isoselenocyanates: Synthesis and Their Use for Preparing Selenium-Based Heterocycles

Neri

Bossmann

2021

Synthesis

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Isoselenocyanates (ISCs) are a class of organoselenium compounds that have been recognized as potential chemotherapeutic and chemopreventative agents against cancer(s) and infectious disease. ISC compounds are chemically analogous to their isosteric relatives, isothiocyanates (ITCs), however possess increased biological activity, such as an increased cytotoxicity against cancer cells. ISCs not only serve as significant products, but also as precursors and essential intermediates for a variety of organoselenium compounds, such as selenium-containing heterocycles which are biologically active. While the syntheses of ISCs have become less difficult to accomplish, the syntheses of selenium-containing heterocycles have been found often difficult due to the use of highly toxic selenium reagents. Because of this, ISCs can serve as versatile reagents in the preparation of these heterocycles. In this review, the classical and recent syntheses of ISCs will be discussed, along with notable and recent synthetic work in using ISCs to access novel selenium-containing heterocycles.

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Synthese und IR‐Spektren von Aryl‐isoselenocyanaten

Cited by 35 publications

References 12 publications

Isocyanide in der Synthese von Stickstoff‐Heterocyclen

Isocyanide in der Synthese von Stickstoff‐Heterocyclen

Synthesis of Isoselenocyanates

Isoselenocyanates: Synthesis and Their Use for Preparing Selenium-Based Heterocycles

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