A new, one-step synthesis of 1-heteroaryl-2-alkylaminoethanols |
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| Authors: | Fuqiang Ning David E Hibbs |
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| Institution: | a Sunderland Pharmacy School, University of Sunderland, Wharncliffe Street, Sunderland SR1 3SD, UK
b Faculty of Pharmacy, Pharmacy Building A15, University of Sydney, Sydney, NSW 2006, Australia |
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| Abstract: | Refluxing a mixture of a heteroarylcarboxaldehyde and an N-alkylamino acid in dry toluene, in the presence of 4 Å molecular sieves, results in the formation of β-hydroxyamines through the 1,3-electrocyclisation of an azomethine ylide and the subsequent ring-opening hydrolysis of an aziridine. The intermediacy of an azomethine ylide in this process is suggested by the isolation of oxazolidines from the cycloaddition of the azomethine ylides to their aldehyde precursors. |
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| Keywords: | Azomethine ylides Decarboxylation β-Hydroxyamines Aziridines Ring-opening |
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