Header

UZH-Logo

Maintenance Infos

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


Widmer, Ulrich; Heimgartner, Heinz; Schmid, Hans (1978). Synthese von 3-Dimethylamino-3a,4,5,7a-tetrahydro-1H-isoindol-1-onen durch intramolekulare Diels-Alder-Reaktion. Helvetica Chimica Acta, 61:815-821.

Abstract

Thermolysis of N2-acylamidines, the acyl group of which derives from an alpha,beta,gamma,delta-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-dimethylamino-2H-azirines (1 and 4) and carboxylic acid chlorides.

Abstract

Thermolysis of N2-acylamidines, the acyl group of which derives from an alpha,beta,gamma,delta-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-dimethylamino-2H-azirines (1 and 4) and carboxylic acid chlorides.

Statistics

Citations

24 citations in Web of Science®
19 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

0 downloads since deposited on 26 Aug 2014
0 downloads since 12 months

Additional indexing

Other titles:Synthesis of 3-Dimethylamino-3a,4,5,7a-tetrahydro-1H-isoindol-1-ones by Intramolecular Diels-Alder Reaction
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1978
Deposited On:26 Aug 2014 15:51
Last Modified:08 Dec 2017 06:59
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
Publisher DOI:https://doi.org/10.1002/hlca.19780610228

Download