A Solid-Phase Synthesis of N,N‘-Disubstituted Ureas and Perhydroimidazo[1,5-a]pyrazines via the Curtius Rearrangement
- 21 September 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (21) , 3309-3311
- https://doi.org/10.1021/ol006383n
Abstract
An efficient method for trapping isocyanates, generated from the Curtius rearrangement, with resin-bound amines is reported. A commercially available carboxylic acid is treated with diphenylphosphoryl azide, followed by thermal rearrangement, cooling, and trapping in one pot. Cleavage from the resin gives an N, N'-disubstituted urea in excellent purity, as demonstrated with several heterocyclic and aliphatic carboxylic acids. Further utility is shown by preparing several novel perhydroimidazo[1,5-a]pyrazines.Keywords
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