Ulrich Widmer, H. Heimgartner, H. Schmid
Mar 8, 1978
Citations
0
Influential Citations
20
Citations
Journal
Helvetica Chimica Acta
Abstract
Synthesis of 3-Dimethylamino-3a,4,5, 7a-tetrahydro-1H-isoindol-1-ones by Intramolecular Diels-Alder Reaction Thermolysis of N2-acylamidines, the acyl group of which derives from an α,β,γ,δ-unsaturated carboxylic acid (2, 5–7), yields 3-dimethylamino-3a,4,5,7a-tetrahydro-1H-isoindol-1-ones (3,8–10, Schemes 1 and 3) in 63–78%. Only the thermodynamically controlled cis-fused ring system is formed. The starting materials are readily available by the reaction of 3-dimethylamino2H-azirines (1 and 4) and carboxylic acid chlorides.