GABRIEL-HEINE Aziridine Isomerization

Gabriel-Heine Aziridine Isomerization Jeremy M. Richter 1.2.1 Description... 

The Gabriel-Heine aziridine isomerization describes the rearrangement of an acylaziridine 1 into an oxazoline 2. " ... 

Much like with total synthesis, the Gabriel-Heine aziridine isomerization has not found widespread application within the medicinal chemistry community, despite its ability to efficiently generate a variety of azoles. DeWald and coworkers at Parke-Davis used the Gabriel-Heine reaction in the preparation of potential antipsychotics. Compound 27 was rearranged upon exposure to sodium iodide in acetone to provide compounds of type 28 in moderate to good yield, which were evaluated as nondopamine-binding antipsychotics. 

Researchers at Sandoz prepared a series of bronchodilators using the Gabriel-Heine aziridine isomerization as a key step. Aziridine 29 was reacted with sodium iodide and acetone to prepare the ring-expanded product 30 in 90% yield. Further manipulations furnished the title compounds 31 in good yield, which were evaluated as bronchodilators. 

Iqbal and co-workers used the Gabriel-Heine aziridine isomerization to confirm the stereochemistry of an intermediate for preparation of an HIV... 

Kohn and Jung reported the conversion of alkenes into vicinal diamines using the Gabriel-Heine aziridine isomerization as a key step during this sequence. Alkene 34 was converted into the aziridine 35 using standard chemistry. Rearrangment under the action of sodium iodide provided the desired imidazolone, which was hydrolyzed with barium hydroxide to give the vicinal diamine 36. 

The Banks and Mattay groups independently reported the use of the Gabriel-Heine aziridine isomerization in the context of fullerenes. Acylaziridinofiillerine 39 was rearranged simply by heating to provide the oxazininofullerine 40 in quantitative yield. 

The Gabriel-Heine aziridine isomerization has seen many other uses since its development, whether in the preparation of starting materials or for studies of fundamental reactivities. ... 

Gabriel-Heine Aziridine Isomerization to Prepare Bronchodilators... 

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