Synfacts 2009(12): 1319-1319  
DOI: 10.1055/s-0029-1218233
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Synthesis of Benzazepines

Contributor(s): Victor Snieckus, Emilie David
Á. González-Gómez*, G. Domínguez, J. Pérez-Castells*
Universidad San Pablo CEU, Madrid, Spain
Further Information

Publication History

Publication Date:
20 November 2009 (online)


Reported here is the cyclization of ortho-acetylenic aniline N-allenyl amides under gold(III) catalysis to give products which vary as a function of substrates and conditions. Thus, cyclization of N-allenyl sulfonamides 1 affords trans-substituted benzazepines 2 using AuCl3 as catalyst and alcohols as nucleophilic traps at low temperature. Under those conditions, the formation of allene addition product 3 was also observed. This may be rationalized by coordination of the metal to the allene, instead of coordination to the alkyne, promoting nucleophilic addition to afford 3. This may, in turn, undergo deallenylation to give 4 (also an observed product), which leads ultimately to benzazepines 2. The intermediacy of 3 under AuCl3 catalysis in the presence of methanol was demonstrated in a separate experiment.