2-Azabicyclo[2.2.2]octa-3,5-dione via a Nitrile Diels−Alder Reaction

2-Azabicyclo[2.2.2]octa-3,5-dione via a Nitrile Diels−Alder Reaction

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...

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Veröffentlicht in:Journal of organic chemistry 2003-10, Vol.68 (21), p.8256-8257
Hauptverfasser: McClure, Cynthia K, Link, Jeffrey S
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034961i