New Opportunities with the Duff Reaction

New Opportunities with the Duff Reaction

The Duff reaction (HMTA, AcOH or TFA) was studied on substituted [6 + 5] heterocyclic compounds. This reaction provides a useful route to aldehydes for compounds bearing sensitive amide functions. It gives also access to tricyclic lactams of potential biological interest. The formation of an aminome...

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Veröffentlicht in:Journal of organic chemistry 2008-08, Vol.73 (15), p.5989-5992
Hauptverfasser: Masurier, Nicolas, Moreau, Emmanuel, Lartigue, Claire, Gaumet, Vincent, Chezal, Jean-Michel, Heitz, Annie, Teulade, Jean-Claude, Chavignon, Olivier
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Chemistry
Coordination chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic Compounds - chemistry
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics and mechanisms
Magnetic Resonance Spectroscopy
Medicinal Chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Radiochemistry
Reactivity and mechanisms
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Beschreibung
Zusammenfassung:The Duff reaction (HMTA, AcOH or TFA) was studied on substituted [6 + 5] heterocyclic compounds. This reaction provides a useful route to aldehydes for compounds bearing sensitive amide functions. It gives also access to tricyclic lactams of potential biological interest. The formation of an aminomethyl intermediate in the Duff reaction mechanism is unequivocally demonstrated.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800700b