Journal
CHEMSUSCHEM
Volume 15, Issue 20, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.202201301
Keywords
diversity-oriented synthesis; atropaldehyde acetals; dual C3; C2-synthon; metal-free catalysis; nitrogen-containing heterocycles
Funding
- National Natural Science Foundation of China [21872060, 21902054, 21761132014, 22072049]
- Fundamental Research Funds for the Central Universities [2019kfyXJJS072]
- Program for HUST Academic Frontier Youth Team [2019QYTD06]
- Innovation and Talent Recruitment Base of New Energy Chemistry and Device
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A highly efficient and elegant diversity-oriented reaction paradigm was developed using atropaldehyde acetals as new dual C2/C3 synthons under metal-free conditions. Glycine esters were used as the counterpart reagents, enabling rapid synthesis of two important nitrogen-containing heterocycles. The manipulation of the substitutional groups of glycine esters controlled the divergent products.
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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