Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes

Abstract

A simple method for the preparation of a variety of N-sulfonyl aziridines (10 examples) from 1,2-amino alcohols under continuous flow conditions is described. Using flow based methods, the aziridines can be further ring opened with oxygen, carbon, and halide nucleophiles or ring expanded to imidazolines by Lewis acid promoted reaction with nitriles. Telescoping the aziridine generation and ring opening steps together in a microfluidic reactor allows the chemistry to be undertaken with limited exposure to the potentially hazardous aziridine intermediates.

Synthesis of Fluorine‐Containing Molecular Entities Through Fluoride Ring Opening of Oxiranes and Aziridines

“…After work‐up and chromatography, product (±)‐356 was obtained in 63 % yield. Synthesis of aziridine 355 was also possible utilizing flow methods …”

Continuous‐Flow Synthesis and Derivatization of Aziridines through Palladium‐Catalyzed C(sp3)−H Activation

“…Although several reactions have been described previously for aziridine ring opening in continuous flow, to the best of our knowledge, none have been performed by using an immobilization–activation strategy. The high purity of the crude mixture (>90 %, 1 H NMR) allows direct transformations of the synthesized amines without any additional treatment.…”

Synthesis of substituted imid(thi)azolidines by [3+2] cycloaddition of aziridines with nitriles(isothiocyanates) via visible light photocatalysis

“…17 Catalyzed by Lewis acid or transition metals, the [3+2] cycloaddition of aziridines with nitriles can be performed to acquire imidazolines. [18][19][20][21][22][23][24] For the synthesis of 2-iminothiazolidines, the [3+2] cycloaddition reaction of aziridines with isothiocayanates could also be accomplished using several catalysts or stoichiometric reagents.…”