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

Abstract

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 H₂O 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.