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. 2008 Aug 1;73(15):5989-92.
doi: 10.1021/jo800700b. Epub 2008 Jul 3.

New opportunities with the Duff reaction

Nicolas Masurier  1 , Emmanuel Moreau, Claire Lartigue, Vincent Gaumet, Jean-Michel Chezal, Annie Heitz, Jean-Claude Teulade, Olivier Chavignon
Affiliations

New opportunities with the Duff reaction

Nicolas Masurier et al. J Org Chem. .

Abstract

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.

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