A multicomponent reaction of isocyanides, selenium powder and 3-aminooxetanes in pure water: green and efficient synthesis of 1,3-selenazolines

Herein, a novel, efficient and metal-free multicomponent reaction of isocyanides, selenium powder and 3-aminooxetanes is reported. The reaction uses selenium powder as the selenium source and H 2 O as the sole reaction medium, delivering a series of 1,3-selenazolines under mild conditions. The trans...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-06, Vol.25 (11), p.4239-4243
Main Authors: Liu, Huan, Ye, Zi-Lin, Cai, Zhong-Jian, Ji, Shun-Jun
Format: Article
Language:English
Subjects:
Atom economy
Biocompatibility
Biological activity
Catalysts
Chemical synthesis
Functional groups
Green chemistry
Organoselenium compounds
Phase transfer catalysts
Powder
Reagents
Selenium
Selenium compounds
Substrates
Transition metals
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Summary:Herein, a novel, efficient and metal-free multicomponent reaction of isocyanides, selenium powder and 3-aminooxetanes is reported. The reaction uses selenium powder as the selenium source and H 2 O as the sole reaction medium, delivering a series of 1,3-selenazolines under mild conditions. The transformation features good functional group compatibility, broad substrate scope and high atom economy, avoiding the use of unstable and toxic selenium agents, additional phase transfer catalysts and transition-metal catalysts, which is in line with the concept of green organic synthesis. In addition, the obtained selenazolines were easily applied to the derivatization of biologically active molecules, which provides a new avenue for the synthesis of drug-like organoselenium compounds. A novel and green multicomponent reaction in aqueous media is developed for the efficient synthesis of 1,3-selenazolines.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc00708a