Abstract
Propargylic amines are important multifunctional building blocks that are frequently exploited in the synthesis of privileged heterocyclic entities. Herein we report on a novel flow process that achieves the safe and effective on-demand synthesis of propargylic amines in a telescoped manner. This process minimizes exposure to hazardous azide intermediates and renders a streamlined route into these building blocks. The value of this approach is demonstrated by the rapid generation of a small selection of drug-like thiazolines that result from a high-yielding reaction cascade between propargylic amines with different aryl isothiocyanates.
Highlights
As modern drug development programs continue to rely on suitably functionalized molecular building blocks, efforts towards their effective preparation remain a challenge at the forefront of modern synthetic chemistry
This was driven by the desire to streamline the synthesis effort avoiding time consuming isolation and purification stages for the potentially hazardous azide intermediate 5 as well as the release of nitrogen gas during the Staudinger reduction step, that could lead to a dangerous run-away process
We have developed a straightforward access to valuable propargylic amines that exploits a telescoped continuous flow approach
Summary
As modern drug development programs continue to rely on suitably functionalized molecular building blocks, efforts towards their effective preparation remain a challenge at the forefront of modern synthetic chemistry. Oftentimes such key building blocks may not be readily available or cannot be stored for long periods of time due to unavoidable degradation, making on-demand synthesis the only option for synthetic chemists. Propargylic amines have recently featured prominently as key components in contemporary syntheses of pyridines [2], imidazoles [3] and oxazolines [4] (Scheme 1).
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