L-Proline catalyzed multi-component synthesis of N -pyridyl-tetrahydroisoquinolines and their α-C(sp 3 )-H oxygenation

Herein, we report an effective multi-component synthesis that starts with readily available starting materials and accesses poly-substituted pyridine derivatives by using L-proline as a benign catalyst. This process uses cyclic amines, aldehydes, and malononitrile in a condensation reaction to produ...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-11, Vol.22 (43), p.8608-8616
Main Authors: Boruah, Aditi, Deb, Mohit L, Thakuria, Ranjit, Baruah, Pranjal K
Format: Article
Language:English
Subjects:
Aldehydes
Amines
Catalysts
Chemical synthesis
Malononitrile
Oxygenation
Proline
Pyridines
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Summary:Herein, we report an effective multi-component synthesis that starts with readily available starting materials and accesses poly-substituted pyridine derivatives by using L-proline as a benign catalyst. This process uses cyclic amines, aldehydes, and malononitrile in a condensation reaction to produce a variety of pyridine derivatives under mild conditions. Furthermore, depending on the catalysts used, the selective synthesis of an amide and/or an aldehyde functionality is achieved through α-C(sp )-H oxygenation of the tertiary amine moiety in the resultant pyridine derivatives. The pyridine ring's nitrogen atom plays a crucial role in accelerating C-H oxygenation at the α-position of the tertiary amine, highlighting the synthetic versatility and usefulness of this method.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob01343c