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Diversity‐Oriented Metal‐Free Synthesis of Nitrogen‐Containing Heterocycles Using Atropaldehyde Acetals as a Dual C3/C2‐Synthon

Von Wiley-VCH zur Verfügung gestellt

Diverse as one can: Atropaldehyde acetals can serve as dual C3/C2-synthons to react selectively with glycine esters in industrially acceptable solvents, that is, diethyl carbonate or acetonitrile, with the aid of trifluoroacetic acid. On the basis of these reactions, diversity-oriented synthesis of nitrogen-containing heterocycles, pyrrolo[1,2-a]quinolines and 3,5-diarylpyridines, is successfully established.


Abstract

A highly efficient and elegant diversity-oriented reaction paradigm employing atropaldehyde acetals as new dual C2/C3 synthons was developed under metal-free conditions using glycine esters as the counterpart reagents, which allowed rapid synthesis of two important nitrogen-containing heterocycles, pyrrolo[1,2-a]quinolines and 3,5-diarylpyridines. The divergent products are subtly controlled by the manipulation of the substitutional groups of glycine esters. When a N-arylglycine ester was used, pyrrolo[1,2-a]quinolines can be formed through cascade oxidative C−C cleavage/multiple cyclization. Instead, N-benzylglycine ester as the counter-reagent led to the synthesis of 3,5-diarylpyridines via two key C−N cleavages. Mild conditions, broad substrate scope, scalability and environmentally acceptable organic solvents rendered this method practical and attractive.

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