Ugi-Type Reaction Enables Access to Fused Imidazole Derivatives for DNA-Encoded Library Technology

Hao Guo, Zitao Li, Gaonan Wang, Biyu Zhang, Mengxue Wang, Lu Liu, Alexander L. Satz, Wenji Su, Letian Kuai, Qi Zhang

Bioconjugate Chemistry 

DOI: 10.1021/acs.bioconjchem.5c00655

Abstract

Abstract Image

This study presents a DNA-compatible synthesis of diverse N-fused imidazopyridines via a catalyst-free Ugi-type multicomponent reaction using TMSCN as a functional isonitrile equivalent. The desilylation activation occurs efficiently in water without additional catalysts. The method exhibits a broad substrate scope for aldehydes and heterocyclic amidines and excellent chemoselectivity, underscoring its utility for constructing privileged heteroaromatic scaffolds in DNA-encoded library technology.

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