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. 2013 Aug 7;11(29):4792-6.
doi: 10.1039/c3ob40523k. Epub 2013 Jun 13.

Various Cyclization Scaffolds by a Truly Ugi 4-CR

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Free PMC article

Various Cyclization Scaffolds by a Truly Ugi 4-CR

Mantosh K Sinha et al. Org Biomol Chem. .
Free PMC article

Abstract

Efficient access to a large chemical space based on new scaffolds with defined 3D conformations and highly variable in the side chains is needed to find novel functional materials. Four heterocyclic scaffolds based on a four component Ugi reaction of α-amino acids, oxo components, isocyanides and primary or secondary amines suitably functionalized are described. A handful of examples are described for each scaffold.

Figures

Fig. 1
Fig. 1
Structure of pyrrolidinedione product 9a in solid state.
Fig. 2
Fig. 2
Structure of Ugi/Pictet-Spengler product 11d in solid state
Fig. 3
Fig. 3
Bicyclic Ugi/condensation product 13c in solid state
Fig. 4
Fig. 4
Principal Moment of Inertia (PMI) calculated for 1,000 randomly generated compounds for each of the four scaffolds 7 (green triangles), 9 (light blue triangles), 11 (purple triangles) and 13 (navy blue triangles) compared to 1,000 randomly chosen compounds from the Zinc Library (yellow squares). PMI of specific compounds from this paper can be seen in all four graphs as red squares.
Fig. 4
Fig. 4
Principal Moment of Inertia (PMI) calculated for 1,000 randomly generated compounds for each of the four scaffolds 7 (green triangles), 9 (light blue triangles), 11 (purple triangles) and 13 (navy blue triangles) compared to 1,000 randomly chosen compounds from the Zinc Library (yellow squares). PMI of specific compounds from this paper can be seen in all four graphs as red squares.
Scheme 1
Scheme 1
Previously reported Ugi 4-CR of α-amino acid, oxo-component, isocyanide and primary or secondary amine

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