Abstract
Isoselenocyanates (ISCs) are a class of organoselenium compounds that have been recognized
as potential chemotherapeutic and chemopreventative agents against cancer(s) and infectious
diseases. ISC compounds are chemically analogous to their isosteric relatives, isothiocyanates
(ITCs); however, they possess increased biological activity, such as enhanced 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 syntheses of ISCs have become less
difficult to accomplish, the syntheses of selenium-containing heterocycles are often
difficult due to the use of highly toxic selenium reagents. Because of this, ISCs
can serve as versatile reagents for 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 employing ISCs to access novel selenium-containing heterocycles.
1 Introduction
1.1 Selenium and Health
2 Isoselenocyanates
2.1 Preparation of Isoselenocyanates
3 Selenium-Containing Heterocycles
3.1 Notable Synthetic Work
3.2 Recent Synthetic Work
3.2.1 Synthesis of N-(3-Methyl-4-phenyl-3H-selenazol-2-ylidene)benzamide Derivatives
3.2.2 Synthesis and X-ray Studies of Diverse Selenourea Derivatives
3.2.3 Synthesis of Heteroarene-Fused [1,2,4]Thiadiazoles/Selenadiazoles via Iodine-Promoted
[3+2] Oxidative Cyclization
3.2.4 2-Amino-1,3-selenazole Derivatives via Base-Promoted Multicomponent Reactions
4 Conclusion
Key words
isoselenocyanides - selenium heterocycles - selenourea - multicomponent reactions
- iodine-promoted cyclization
