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Synfacts 2006(12): 1214-1214
DOI: 10.1055/s-2006-955562
DOI: 10.1055/s-2006-955562
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Heteroring Annulation Using TandemN-Acylamide Methylenation-RCM
M. L. Bennasar*, T. Roca, M. Monerris, D. García-Díaz
University of Barcelona, Spain
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-955562-1.jpg)
Significance
Sequential Petasis and Grubbs metathesis reactions are involved in the construction of indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines from simple ortho-substituted anilines and benzylamines. Thus methylenation of N-acylamides and Grubbs’ II catalyzed ring-closing metathesis (RCM) of the resulting enamides lead to heteroannulated products in moderate overall yields. This reaction sequence appears to be general and may be also used to synthesize other heterocyclic compounds such as benzazepines and benzoxazepines. Slow RCM reactions and alkene isomerization appear to be responsible for the low yields of these processes whose scope was insufficiently tested.