𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Diels-alder reactions of the heterodiene system in 2(1h)-pyrazinones

✍ Scribed by M. Tutonda; D. Vanderzande; J. Vekemans; S. Toppet; G. Hoornaert

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
235 KB
Volume
27
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Variously substituted 2(1H-pyrazinones react with acetylenic derivatives to give specifically substituted pyridones or pyridines. The observed selectivity can be explained in terms of HO-LU interactions for the reagents and two competitive retro Diets-Alder reactions of the primary bicycloadducts. With cyanotosylate as dienophile no pyrimidone derivative but a new 2C'lH)-pyrazinone is obtained.

📜 SIMILAR VOLUMES

Stereoselective intramolecular Diels–Ald
Stereoselective intramolecular Diels–Alder reactions of 3-alkenyl(oxy)-2(1H)-pyrazinones
✍ Wim M. De Borggraeve; Frederik J.R. Rombouts; Bie M.P. Verbist; Erik V. Van der 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 78 KB

Dichloropyrazinones are reacted with alkenolates or a Grignard reagent in order to tether a dienophilic side-chain at the 3-position. The compounds smoothly undergo intramolecular Diels-Alder reaction forming tricyclic ring systems. The reactions proceed completely stereoselective yielding only endo