Journal of Combinatorial Chemistry 2006-01-01

Annulation of primary amines to piperazines and diazaspirocycles utilizing alpha-methyl benzyl resin.

Calum Macleod, Blanca I Martinez-Teipel, William M Barker, Roland E Dolle

Index: J. Comb. Chem. 8 , 132, (2006)

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Abstract

The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates. Critical to the success of this chemistry was the development of alpha-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.