Synthese von 3-Dimethylamino-3a,4,5,7a-tetrahydro-1H-iso-indol-1-onen durch intramolekulare Diels-Alder-Reaktion

✍ Scribed by Ulrich Widmer; Heinz Heimgartner; Hans Schmid

• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: German
• Weight: 460 KB
• Volume: 61
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19780610228

✦ Synopsis

Synthesis of 3‐Dimethylamino‐3a,4,5, 7a‐tetrahydro‐1__H__‐isoindol‐1‐ones by Intramolecular Diels‐Alder Reaction

Thermolysis of N^2^‐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‐dimethylamino2__H__‐azirines (1 and 4) and carboxylic acid chlorides.