2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.
Cynthia K McClure, Jeffrey S Link
Index: J. Org. Chem. 68(21) , 8256-7, (2003)
Full Text: HTML
Abstract
The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable adduct. Hydrolysis of the tosyl cyanide adduct resulted in the isoquinuclidinone 2-aza[2.2.2]octa-3,5-dione as a crystalline compound in excellent yield from the nitrile.
Related Compounds
Related Articles:
High-Temperature Diels-Alder Reactions: Transfer from Batch to Continuous Mode. Abele S, et al.
[Org. Process Res. Dev. 16(5) , 1114-1120, (2011)]
Design and Scale-Up of Diels-Alder Reactions for the Practical Synthesis of 5-Phenylbicyclo [2.2. 2] oct-5-en-2-one. Funel JA, et al.
[Org. Process Res. Dev. 15(6) , 1420-1427, (2011)]
Safety Assessment of Diels-Alder Reactions with Highly Reactive Acrylic Monomers. Abele S, et al.
[Org. Process Res. Dev. 16(12) , 2015-2020, (2012)]