Highly efficient and diastereoselective synthesis of new pyrazolylpyrrolizine and pyrazolylpyrrolidine derivates by a three-component domino process.
Diastereoselective reactions between 4-formylpyrazoles, N-substituted maleimides and glycine derivates led to new series of pyrazolyldipyrrolo [3,4-a:3',4'-f]pyrrolizines and pyrazolylpyrrolo[3,4-c]pyrroles in good yields. The reactions proceeded by a domino process through azomethine ylides formed in situ via a 1,3-dipolar cycloaddition reaction.
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia. jairo.quiroga@correounivalle.edu.co.
Jairo
J
Quiroga
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia. jaimegalvez.n@gmail.com.
Jaime
J
Gálvez
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia. rodrigo.abonia@correounivalle.edu.co.
Rodrigo
R
Abonia
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia. braulio.insuasty@correounivalle.edu.co.
Braulio
B
Insuasty
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, Cali 760032, Colombia. alejandro.ortiz@correounivalle.edu.co.
Alejandro
A
Ortíz
Department of Inorganic and Organic Chemistry, Universidad de Jaén, Jaén 23071, Spain. jcobo@ujaen.es.
Justo
J
Cobo
Department of Inorganic and Organic Chemistry, Universidad de Jaén, Jaén 23071, Spain. mmontiel@ujaen.es.
Manuel
M
Nogueras
D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D005998:Glycine / Q000031:analogs & derivatives; D008301:Maleimides / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
D001391:Azo Compounds; D008301:Maleimides; D011758:Pyrroles; D013882:Thiosemicarbazones; C512188:azomethine; D005998:Glycine