New Opportunities with the Duff Reaction

• Published in: Journal of organic chemistry Vol. 73; no. 15; pp. 5989 - 5992
• Main Authors: Masurier, Nicolas, Moreau, Emmanuel, Lartigue, Claire, Gaumet, Vincent, Chezal, Jean-Michel, Heitz, Annie, Teulade, Jean-Claude, Chavignon, Olivier
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.2008; Amer Chemical Soc
• Subjects: Chemical Sciences; Chemistry; Chemistry, Organic; 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; Physical Sciences; Preparations and properties; Radiochemistry; Reactivity and mechanisms; Science & Technology; POTENT ACTIVITY; FORMYLATION; NITROGEN HETEROCYCLIC COMPOUNDS; HEXAMETHYLENETETRAMINE; IMIDAZO<1,2-A>PYRIDINES; N-CHLOROSUCCINIMIDE; RING-SYSTEM; SUBSTITUTION REACTIONS; REIMER-TIEMANN REACTION; DERIVATIVES; Duff reaction; Amine; Nitrogen heterocycle; Lactam; Reaction mechanism; Carboxamide; Acetic acid; Aldehyde; Tricyclic compound; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo800700b

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.