Solution-phase parallel synthesis of spirohydantoins.
Spirohydantoins are considered privileged structures, making them attractive for the preparation of compound libraries with the potential for diverse biological activity. However, very few modifications of this scaffold have been reported to date. The spirohydantoin template was elaborated into a library of 168 compounds through a two-step solution-phase parallel synthesis starting from various N-substituted piperidinones. The Strecker reaction was employed to generate alpha-amino nitriles from aniline and TMSCN (or KCN). Subsequent reaction of the anilido nitrogen with a diverse set of isocyanates, followed by refluxing under acidic conditions, afforded the title library in high yield and purity.
Nieto
Marcelo J
MJ
Department of Medicinal Chemistry and Laboratory for Applied Drug Design and Synthesis, School of Pharmacy, University of Mississippi, University, Mississippi 38677, USA.
Philip
Ashok E
AE
Poupaert
Jacques H
JH
McCurdy
Christopher R
CR
D020650:Combinatorial Chemistry Techniques; D015195:Drug Design; D006827:Hydantoins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012996:Solutions; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006827:Hydantoins; D012996:Solutions; D013141:Spiro Compounds