Cyano Diels−Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines
- 3 September 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (38), 13203-13205
- https://doi.org/10.1021/ja106901u
Abstract
Two metal-free, formal [2 + 2 + 2] cycloaddition strategies for the construction of polycyclic pyridine derivatives are described that proceed via pericyclic cascade mechanisms featuring the participation of unactivated cyano groups as enophile and dienophile cycloaddition partners.This publication has 19 references indexed in Scilit:
- Formal [2 + 2 + 2] Cycloaddition Strategy Based on an Intramolecular Propargylic Ene Reaction/Diels−Alder Cycloaddition CascadeJournal of the American Chemical Society, 2010
- Ene reactions between two alkynes? Doors open to thermally induced cycloisomerization of macrocyclic triynes and enediynesChemical Communications, 2010
- The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactionsChemical Society Reviews, 2007
- Ene Reaction of Arynes with AlkynesJournal of the American Chemical Society, 2006
- gem-Disubstituent Effect: Theoretical Basis and Synthetic ApplicationsChemical Reviews, 2005
- Construction of Pyridine Rings by Metal-Mediated [2 + 2 + 2] CycloadditionChemical Reviews, 2003
- First Partially Intramolecular Palladium‐Catalyzed [2+2+2] Cycloaddition of Benzyne: Application to the Synthesis of Benzo[b]fluorenonesEuropean Journal of Organic Chemistry, 2003
- Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Ynones. Formation of Polycyclic Furans via the Generation and Rearrangement of Strained Heterocyclic AllenesJournal of the American Chemical Society, 1998
- THE ENE REACTION OF TRISUBSTITUTED ALKENES WITH ELECTRON-DEFICIENT NITRILES IN THE PRESENCE OF BORON TRICHLORIDEChemistry Letters, 1985
- A New Stereoselective Approach to Substituted Pyrrolidines by Intramolecular Ene‐Reactions. Preliminary communicationHelvetica Chimica Acta, 1973