Evolution of Natural Product Scaffolds by Acyl- and Arylnitroso Hetero-Diels−Alder Reactions: New Chemistry on Piperine
The Journal of Organic Chemistry2008Vol. 73(12), pp. 4559–4567
Citations Over TimeTop 12% of 2008 papers
Abstract
Piperine, a natural product containing a conjugated diene, was reacted with polymer-supported acyl- and arylnitroso dienophiles. The reactions with arylnitroso dienophiles were also carried out in solution. The oxazine rings formed by the corresponding hetero-Diels-Alder reactions were further transformed and novel acyclic as well as heterocyclic derivatives including pyrroles and quinoxalinones were prepared.
Related Papers
- → Diene-transmissive hetero Diels–Alder reaction of cross-conjugated azatrienes with ketenes: a novel and efficient, stereo-controlled synthetic method for hexahydroquinolinones(2002)29 cited
- → Chemistry of 2,5-bis(trimethylsiloxy) furans. I: Preparation and diels-alder reactions(1980)62 cited
- → Diene-transmissive hetero-Diels–Alder reaction of cross-conjugated azatrienes: a novel and efficient method for the synthesis of ring-fused nitrogen heterocycles(1997)26 cited
- → Diene-transmissive Hetero Diels-Alder Reactions of Bis(silyloxy) Cross-conjugated Trienes with Azodicarbonyl Compounds(1994)23 cited
- → ChemInform Abstract: Switched Role of Fullerene in the Diels—Alder Reaction: Facile Addition of Dienophiles to the Conjugated Fullerene Diene Moiety.(2009)1 cited