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.

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.

Citations

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:05 Apr 2016 18:21
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
Permanent URL: https://doi.org/10.5167/uzh-98342

Download

[img]
Filetype: PDF - Registered users only
Size: 471kB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations