Efficient Approaches toward the Solid-Phase Synthesis of New Heterocyclic Azoniaspiro Ring Systems:Synthesis of Tri- and Tetrasubstituted 10-Oxo-3,9-diaza-6-azoniaspiro[5.5]undecanes

摘要

An efficient approach for the parallel solid-phase synthesis of novel heterocyclic azoniaspiro ring systems is described.The target compounds,the 1,8,9-trisubstituted 10-oxo-3,9-diaza-6-azoniaspiro[5.5]undecanes,were obtained starting from resin-bound reduced dipeptides.The azoniaspiro cation was formed by intramolecular attack of a tertiary nitrogen on pendent alpha-bromocarbonyl.N-3 acylated and N-3 alkyl-amino carbonyl derivatives of the 1,8,9-trisubstituted 10-oxo-3,9-diaza-6-azoniaspiro[5.5]undecanes were obtained following in solution treatment of the N-3 azoniaspiro derivatives with different carboxylic acids and isocyanates.