High-Speed Microwave-Promoted Hetero-Diels−Alder Reactions of 2(1H)-Pyrazinones in Ionic Liquid Doped Solvents
- 4 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (22) , 7904-7907
- https://doi.org/10.1021/jo0263216
Abstract
Inter- and intramolecular hetero-Diels−Alder reactions in a series of functionalized 2(1H)-pyrazinones were investigated under controlled microwave irradiation. The cycloaddition reactions were efficiently performed in sealed tubes, utilizing either a combination of 1,2-dichloroethane and a thermally stable ionic liquid, or 1,2-dichlorobenzene as reaction medium. In all cases, a significant rate-enhancement using microwave flash heating as compared to thermal heating was observed.Keywords
This publication has 14 references indexed in Scilit:
- Stereoselective intramolecular Diels–Alder reactions of 3-alkenyl(oxy)-2(1H)-pyrazinonesTetrahedron Letters, 2002
- Synthesis of a conformationally restricted dipeptide analogue and its evaluation as a β-turn mimicTetrahedron Letters, 2001
- The Catalytic Conversion of C1−Cn Hydrocarbons to Olefins and Hydrogen: Microwave-Assisted C−C and C−H Bond ActivationEnergy & Fuels, 2000
- A Novel Borosilicate Cage Compound with an Incomplete B4Si4 Cube Structure: [(tBuSi)4(CH2=CHC6H4B)4O10]Published by Wiley ,2000
- Diels-Alder reactions in room-temperature ionic liquidsTetrahedron Letters, 1999
- Diels–Alder reactions in ionic liquidsGreen Chemistry, 1999
- Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinonesTetrahedron, 1998
- Dielectric parameters relevant to microwave dielectric heatingChemical Society Reviews, 1998
- 2(1H)‐Pyrazinones and 2H‐1,4‐Oxazin‐2‐ones and their use in Heterocyclic SynthesisBulletin des Sociétés Chimiques Belges, 1994
- Generation of specifically substituted pyridines and pyridones from 2(1h) pyrazinones and acetylenes : A FMO descriptionTetrahedron, 1990