Header

UZH-Logo

Maintenance Infos

1,3-Dipolar Cycloadditions with 1-Alkoxy-substituted Nitrile Ylides


Bojkova, Nina; Heimgartner, Heinz (1998). 1,3-Dipolar Cycloadditions with 1-Alkoxy-substituted Nitrile Ylides. Heterocycles, 47(2):781-792.

Abstract

Thermolysis of 4-alkoxy-l,3-oxazol-5(2H)-ones (2) (X = O) leads to reactive nitrile ylides (1) bearing an alkoxy substituent at the nitrile C-atom. These intermediates can be trapped by C,C-, C,O-, C,N-, and C,S-dipolarophiles, yielding 5-membered heterocycles via 1,3- dipolar cycloaddition. In the case of 1,3-thiazole-5(4H)-thiones (11) as dipolarophiles, two regioisomeric cycloadducts were obtained. The results of the cycloadditions are discussed with respect to the influence of the alkoxy substituent on the structure of the nitrile ylide.

Abstract

Thermolysis of 4-alkoxy-l,3-oxazol-5(2H)-ones (2) (X = O) leads to reactive nitrile ylides (1) bearing an alkoxy substituent at the nitrile C-atom. These intermediates can be trapped by C,C-, C,O-, C,N-, and C,S-dipolarophiles, yielding 5-membered heterocycles via 1,3- dipolar cycloaddition. In the case of 1,3-thiazole-5(4H)-thiones (11) as dipolarophiles, two regioisomeric cycloadducts were obtained. The results of the cycloadditions are discussed with respect to the influence of the alkoxy substituent on the structure of the nitrile ylide.

Statistics

Citations

7 citations in Web of Science®
10 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 12 Nov 2013
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1998
Deposited On:12 Nov 2013 13:52
Last Modified:05 Apr 2016 17:07
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Professor Hans. E. Schmid-Stiftung
Publisher DOI:https://doi.org/10.3987/COM-97-S(N)74

Download

Preview Icon on Download
Content: Published Version
Filetype: PDF - Registered users only
Size: 330kB
View at publisher

Article Networks

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