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.
[Reaction: see text]. 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 alkylamino 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.
Nefzi
Adel
A
Torrey Pines Institute for Molecular Studies, 3500 General Atomics Court, San Diego, California 92124, USA. adeln@tpims.org
Santos
Rodegar T
RT
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure
D000473:Alkanes; D001372:Aza Compounds; D006571:Heterocyclic Compounds; C022884:undecane