Peptidomimetics are designed to circumvent problems associated with a natural peptide such as stability against proteolysis and poor bioavailability. Such molecules have high pharmacological relevance, especially since receptor selectivity or potency can be substantially improved through effective medicinal chemistry design principles. The Ugi multi-component reaction (MCR) involving an aldehyde, amine, isocyanide, and carboxylic acid is known to produce diverse molecules containing a dipeptide-like backbone. The Ugi MCR offers several advantages in constructing functionalized structures in an operationally friendly and atom economic fashion. Additionally, 1,5-disubstituted tetrazoles, effectively accessed through Ugi-Azide MCR, have been shown to be cis-amide bond surrogates. Heterocycles containing this motif and a peptide backbone are thus of high interest and several routes are being investigated to deliver previously unexplored diverse molecular framework. This talk will cover the generation of unique and complex small molecules synthesized from Ugi MCR followed by intramolecular chemical transformation in domino processes.

Assembly of unique and complex heterocycles generated via post-condensation of Ugi multicomponent reaction products

244th National Meeting (2012)

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