Abstract

GARCIA-GUTIERREZ, Hugo A.; ROMAN-MARIN, Luisa U.; HERNANDEZ-HERNANDEZ, Juan D.  and  CERDA-GARCIA-ROJAS, Carlos M.. Preparación de bases de Schiff y transposición de Beckmann en derivados del longipinano. Rev. latinoam. quím [online]. 2012, vol.40, n.3, pp.210-224. ISSN 0370-5943.

In order to increase the knowledge on the chemical study of longipinane derivatives, a series of Schiff bases of the natural product rastevione (1) and derivatives 2 and 3 was prepared taking advantage of the carbonyl group at C-1 in the six-membered ring of these substances. The chemical behavior of longipinane derivatives (1-3) was typical as carbonyl containing compounds which react in the presence of 2,4-dinitrophenylhydrazine, semicarbazide hydrochloride and hydroxylamine hydrochloride. Oximes (10-12) were subjected to Beckmann rearrangement conditions yielding lactams (13-15). This reaction allowed introduction of a nitrogen atom in the longipinane skeleton, besides this is the first time that the four-membered ring is not involved in a molecular rearrangement of this system.

Keywords : longipinane derivatives; rastevione; Schiff bases; Beckmann rearrangement.