Abstract
The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using cyclopentyl methyl ether (CPME) as an environmentally benign solvent, resulting into a sustainable, safe and potentially automatable method for the synthesis of interesting strained compounds.
Highlights
Since their conception in the early 1990s, Green Chemistry Principles (GCP) have been applied with increasing effort towards the design of efficient production processes [1,2,3]
We investigated the thermally induced cyclisation of 1-(1-azidovinyl)-4-methylbenzene (1a) in refluxing 2-MeTHF and cyclopentyl methyl ether (CPME) as green solvent candidates, and compared the results with the reaction conducted in toluene (Table 1)
A solution of 1-(1azidovinyl)-4-methylbenzene (1a, 0.25 M in CPME) was introduced, via a high pressure syringe pump, into the coil reactor maintained at the temperature of 130 °C, and the residence time varied by adjusting the flow rate (Table 2)
Summary
Since their conception in the early 1990s, Green Chemistry Principles (GCP) have been applied with increasing effort towards the design of efficient production processes [1,2,3]. In 2013, Kirschning harnessed the photoinduced electrocyclization of vinyl azides in a microfluidic photoreactor yielding 2H-azirines as precursors of 1,3-dipolarophiles (Scheme 1a) [27]. Kappe reported the generation of 2H-azirines under continuous flow conditions, and their transformation into functionalized oxazoles using acetone as the solvent (Scheme 1c) [28]. We report a sustainable mixed flow-batch approach that enables the direct preparation of functionalized NH-aziridines from vinyl azides.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
