37848-70-7Relevant articles and documents
Complex polycyclic lactams from pericyclic cascade reactions of Zincke aldehydes
Steinhardt, Sarah E.,Vanderwal, Christopher D.
supporting information; experimental part, p. 7546 - 7547 (2009/10/17)
(Chemical Equation Presented) In the course of a simple mechanistic study on the rearrangement of Zincke aldehydes to Z-α,β,γ,δ- unsaturated amides, a thermally induced pericyclic cascade rearrangement that converts Zincke aldehydes derived from allylic and homoallylic amines into polycyclic lactams was discovered. The key reaction involves an E-Z alkene isomerization, a 6? electrocyclic ring closure, a[1,5]-sigmatropic shift of hydrogen, a 6? electrocyclic ring-opening , and a Diels-Alder cycloaddition, and proceeds with excellent stereoselectivity. The unusual observation that furans and an indole serve as dienophiles in this cascade reaction permitted the synthesis of complex, functional group-rich tri- and tetracyclic lactams. In all cases, the rigid polycyclic products are available in only two steps from pyridinium salts and the allylic or homoallylic secondary amines.
Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement
Bremner, John B.,Perkins, David F.
, p. 2659 - 2665 (2007/10/03)
This paper describes the synthesis of functionalised azecine and azonine derivatives incorporating the adrenaline motif. In a key step, an enolate assisted aza Claisen rearrangement was employed to interconvert from 6- and 5-membered heterocycles to their corresponding 10- and 9-membered lactams.
A metallocarbenoid approach to the formation of spirocyclic ammonium ylides leading to the preparation of medium-sized azacane rings
Wright, Dennis L.,Weekly, R. Matt,Groff, Royce,McMills, Mark C.
, p. 2165 - 2168 (2007/10/03)
A novel approach to azacyclooctene and azacyclononene containing substrates has been achieved via the intermediacy of a spirocyclic ammonium ylide derived from the diazodecomposition of a tethered α-diazoester moiety.
