Regioselective multicomponent sequential synthesis of hydantoins.
The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry.
Department of Chemistry, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano, via Mancinelli 7, 20131 Milano, Italy.
Francesca
F
Olimpieri
Maria Cristina
MC
Bellucci
Tommaso
T
Marcelli
Alessandro
A
Volonterio
D001386:Azides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D002626:Chemistry, Pharmaceutical; D055808:Drug Discovery / Q000379:methods*; D006827:Hydantoins / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D015394:Molecular Structure; D013861:Thiocyanates / Q000737:chemistry
D001386:Azides; D002264:Carboxylic Acids; D006827:Hydantoins; D006846:Hydrocarbons, Halogenated; D017953:Isocyanates; D013861:Thiocyanates